organic compounds
N,N-Diethyl-2-(4-methylbenzenesulfonamido)benzamide
aChemistry Department, Menarini Ricerche S.p.A., Via dei Sette Santi 3, I-50131 Firenze, Italy, and bDip. Energetica "Sergio Stecco", University of Firenze, Via S. Marta 3, I-50139 Firenze, Italy
*Correspondence e-mail: paolapaoli@unifi.it
The 18H22N2O3S, contains two molecules, exhibiting similar conformations [C—S—N—C torsion angles of −82.2 (2) and −70.4 (2)°, and dihedral angles between the mean planes of the aromatic rings of 56.6 (6) and 51.6 (6)° in molecules I and II, respectively]. However, the two independent molecules show distinctly different hydrogen-bonding patterns. In the crystal, molecules I form inversion dimers via pairs of N—H⋯O hydrogen bonds, whereas for molecules II the N—H⋯O hydrogen bond is intramolecular. The hydrogen-bonded dimers of I further propagate along the b-axis direction through π–π interactions [the distance between ring centroids is 3.8424 (8) Å].
of the title compound, CRelated literature
For the synthesis of the title compound, see: Bakker et al. (1997); Kaul et al. (2002). For the biological activity of compounds having the sulfonamide –SO2NH– group, see: Lu & Tucker (2007); Tappe et al. (2008); Chegwidden et al. (2000); Purushottamachar et al. (2008). For structural and conformational studies of molecules featuring the sulfonamide moiety, see: Parkin et al. (2008); Perlovich et al. (2009, 2011); Altamura et al. (2009); Vega-Hissi et al. (2011).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97, WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).
Supporting information
10.1107/S160053681204264X/ld2075sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681204264X/ld2075Isup2.hkl
Supporting information file. DOI: 10.1107/S160053681204264X/ld2075Isup3.cml
For the synthesis of the title compound, see: Bakker et al. (1997); Kaul et al., (2002). Crystals of N,N-diethyl-2-(4-methylphenylsulfonamido)benzamide suitable for single-crystal X-ray
were obtained by slow evaporation of an ethanol/water solution of N,N-diethyl-2-(4-methylphenylsulfonamido)benzamide.The N—H H atoms were located in the Fourier difference map and their coordinates were refined with Uiso(H) = 1.2Ueq(N). All other H atoms were positioned using idealized geometry, and refined using a riding model with Uiso(H) 1.2 times Ueq(C) (1.5 for methyl H atoms).
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell
CrysAlis CCD (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).C18H22N2O3S | Z = 4 |
Mr = 346.43 | F(000) = 736 |
Triclinic, P1 | Dx = 1.346 Mg m−3 |
a = 9.4674 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.2882 (9) Å | θ = 4.1–28.6° |
c = 16.0569 (12) Å | µ = 0.21 mm−1 |
α = 108.426 (7)° | T = 150 K |
β = 97.357 (6)° | Parallelepiped, colourless |
γ = 100.245 (6)° | 0.54 × 0.43 × 0.38 mm |
V = 1709.7 (2) Å3 |
Oxford Diffraction Xcalibur3 CCD diffractometer | 7512 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 4728 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 16.4547 pixels mm-1 | θmax = 28.7°, θmin = 4.1° |
ω scans | h = −12→11 |
Absorption correction: multi-scan (ABSPACK in CrysAlis RED; Oxford Diffraction, 2006) | k = −15→16 |
Tmin = 0.894, Tmax = 1.000 | l = −21→21 |
17890 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0677P)2] where P = (Fo2 + 2Fc2)/3 |
7512 reflections | (Δ/σ)max = 0.001 |
441 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
C18H22N2O3S | γ = 100.245 (6)° |
Mr = 346.43 | V = 1709.7 (2) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.4674 (6) Å | Mo Kα radiation |
b = 12.2882 (9) Å | µ = 0.21 mm−1 |
c = 16.0569 (12) Å | T = 150 K |
α = 108.426 (7)° | 0.54 × 0.43 × 0.38 mm |
β = 97.357 (6)° |
Oxford Diffraction Xcalibur3 CCD diffractometer | 7512 independent reflections |
Absorption correction: multi-scan (ABSPACK in CrysAlis RED; Oxford Diffraction, 2006) | 4728 reflections with I > 2σ(I) |
Tmin = 0.894, Tmax = 1.000 | Rint = 0.025 |
17890 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | Δρmax = 0.42 e Å−3 |
7512 reflections | Δρmin = −0.32 e Å−3 |
441 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | 1.22768 (5) | 0.28575 (4) | −0.00356 (3) | 0.02970 (14) | |
O1 | 1.18234 (15) | 0.23441 (12) | −0.09887 (8) | 0.0365 (3) | |
O2 | 1.36507 (14) | 0.36978 (12) | 0.03457 (9) | 0.0365 (3) | |
O3 | 1.03929 (14) | −0.01020 (12) | 0.08734 (9) | 0.0329 (3) | |
N1 | 1.23284 (17) | 0.17480 (15) | 0.03138 (10) | 0.0278 (4) | |
HN1 | 1.158 (2) | 0.1167 (18) | 0.0058 (13) | 0.033* | |
N2 | 0.98318 (16) | 0.13823 (13) | 0.19374 (10) | 0.0257 (4) | |
C1 | 1.0900 (2) | 0.35179 (16) | 0.03962 (12) | 0.0268 (4) | |
C2 | 1.1191 (2) | 0.42734 (17) | 0.12797 (13) | 0.0311 (5) | |
H2 | 1.2108 | 0.4429 | 0.1638 | 0.037* | |
C3 | 1.0114 (2) | 0.47931 (17) | 0.16265 (13) | 0.0331 (5) | |
H3 | 1.0315 | 0.5296 | 0.2220 | 0.040* | |
C4 | 0.8731 (2) | 0.45770 (17) | 0.11021 (13) | 0.0308 (5) | |
C5 | 0.8479 (2) | 0.38376 (18) | 0.02171 (14) | 0.0348 (5) | |
H5 | 0.7570 | 0.3698 | −0.0146 | 0.042* | |
C6 | 0.9537 (2) | 0.33011 (18) | −0.01428 (13) | 0.0334 (5) | |
H6 | 0.9339 | 0.2802 | −0.0737 | 0.040* | |
C7 | 1.30951 (19) | 0.18780 (16) | 0.11830 (12) | 0.0262 (4) | |
C8 | 1.23673 (19) | 0.14737 (16) | 0.17723 (12) | 0.0257 (4) | |
C9 | 1.3163 (2) | 0.15919 (17) | 0.26008 (12) | 0.0304 (5) | |
H9 | 1.2691 | 0.1312 | 0.2991 | 0.037* | |
C10 | 1.4645 (2) | 0.21191 (18) | 0.28524 (13) | 0.0343 (5) | |
H10 | 1.5162 | 0.2206 | 0.3411 | 0.041* | |
C11 | 1.5345 (2) | 0.25127 (18) | 0.22645 (13) | 0.0332 (5) | |
H11 | 1.6340 | 0.2868 | 0.2431 | 0.040* | |
C12 | 1.4591 (2) | 0.23881 (17) | 0.14310 (13) | 0.0305 (5) | |
H12 | 1.5082 | 0.2644 | 0.1037 | 0.037* | |
C13 | 0.7557 (2) | 0.51226 (19) | 0.14887 (15) | 0.0397 (5) | |
H13A | 0.6650 | 0.4798 | 0.1062 | 0.060* | |
H13B | 0.7826 | 0.5960 | 0.1626 | 0.060* | |
H13C | 0.7444 | 0.4959 | 0.2026 | 0.060* | |
C14 | 1.0785 (2) | 0.08570 (17) | 0.14925 (12) | 0.0250 (4) | |
C15 | 0.82675 (19) | 0.07980 (17) | 0.16405 (13) | 0.0293 (4) | |
H15A | 0.7766 | 0.1054 | 0.2133 | 0.035* | |
H15B | 0.8154 | −0.0048 | 0.1472 | 0.035* | |
C16 | 0.7572 (2) | 0.10750 (18) | 0.08525 (13) | 0.0326 (5) | |
H16A | 0.6554 | 0.0680 | 0.0677 | 0.049* | |
H16B | 0.8054 | 0.0810 | 0.0360 | 0.049* | |
H16C | 0.7666 | 0.1911 | 0.1020 | 0.049* | |
C17 | 1.0220 (2) | 0.25858 (16) | 0.25954 (12) | 0.0291 (4) | |
H17A | 0.9527 | 0.3020 | 0.2443 | 0.035* | |
H17B | 1.1183 | 0.2979 | 0.2561 | 0.035* | |
C18 | 1.0228 (2) | 0.26194 (18) | 0.35513 (13) | 0.0373 (5) | |
H18A | 1.0486 | 0.3424 | 0.3951 | 0.056* | |
H18B | 1.0930 | 0.2208 | 0.3712 | 0.056* | |
H18C | 0.9272 | 0.2247 | 0.3594 | 0.056* | |
S1' | 0.36428 (5) | 0.62169 (4) | 0.38496 (3) | 0.02947 (14) | |
O1' | 0.25700 (14) | 0.66660 (13) | 0.43239 (9) | 0.0389 (4) | |
O2' | 0.34408 (14) | 0.49807 (12) | 0.34048 (9) | 0.0356 (3) | |
O3' | 0.71780 (14) | 0.88703 (11) | 0.52660 (9) | 0.0346 (3) | |
N1' | 0.51694 (17) | 0.66700 (15) | 0.46038 (11) | 0.0279 (4) | |
HN1' | 0.534 (2) | 0.7376 (18) | 0.4848 (14) | 0.033* | |
N2' | 0.81608 (16) | 0.90225 (13) | 0.40820 (10) | 0.0263 (4) | |
C1' | 0.39078 (18) | 0.69322 (17) | 0.30717 (12) | 0.0273 (4) | |
C2' | 0.45199 (19) | 0.64421 (18) | 0.23389 (13) | 0.0297 (4) | |
H2' | 0.4787 | 0.5727 | 0.2251 | 0.036* | |
C3' | 0.4727 (2) | 0.70303 (18) | 0.17430 (13) | 0.0316 (5) | |
H3' | 0.5144 | 0.6706 | 0.1256 | 0.038* | |
C4' | 0.43286 (19) | 0.80900 (18) | 0.18556 (13) | 0.0314 (5) | |
C5' | 0.3715 (2) | 0.85577 (19) | 0.25892 (14) | 0.0369 (5) | |
H5' | 0.3431 | 0.9265 | 0.2671 | 0.044* | |
C6' | 0.3517 (2) | 0.79973 (18) | 0.32016 (13) | 0.0345 (5) | |
H6' | 0.3124 | 0.8333 | 0.3697 | 0.041* | |
C7' | 0.64714 (19) | 0.63062 (17) | 0.43794 (12) | 0.0246 (4) | |
C8' | 0.76801 (19) | 0.71269 (16) | 0.43306 (12) | 0.0251 (4) | |
C9' | 0.8955 (2) | 0.67471 (17) | 0.41748 (12) | 0.0279 (4) | |
H9' | 0.9765 | 0.7277 | 0.4145 | 0.034* | |
C10' | 0.9044 (2) | 0.56046 (18) | 0.40639 (13) | 0.0319 (5) | |
H10' | 0.9906 | 0.5369 | 0.3963 | 0.038* | |
C11' | 0.7839 (2) | 0.48063 (17) | 0.41038 (13) | 0.0316 (5) | |
H11' | 0.7894 | 0.4033 | 0.4025 | 0.038* | |
C12' | 0.6555 (2) | 0.51581 (17) | 0.42602 (13) | 0.0293 (4) | |
H12' | 0.5750 | 0.4620 | 0.4285 | 0.035* | |
C13' | 0.4544 (2) | 0.8733 (2) | 0.12051 (14) | 0.0437 (6) | |
H13D | 0.5286 | 0.8482 | 0.0885 | 0.066* | |
H13E | 0.4842 | 0.9567 | 0.1528 | 0.066* | |
H13F | 0.3642 | 0.8559 | 0.0789 | 0.066* | |
C14' | 0.76384 (19) | 0.84015 (17) | 0.45779 (12) | 0.0263 (4) | |
C15' | 0.8238 (2) | 1.02962 (17) | 0.44075 (13) | 0.0318 (5) | |
H15C | 0.9033 | 1.0690 | 0.4203 | 0.038* | |
H15D | 0.8465 | 1.0589 | 0.5057 | 0.038* | |
C16' | 0.6845 (2) | 1.0613 (2) | 0.40996 (15) | 0.0457 (6) | |
H16D | 0.6968 | 1.1454 | 0.4334 | 0.069* | |
H16E | 0.6056 | 1.0244 | 0.4312 | 0.069* | |
H16F | 0.6624 | 1.0344 | 0.3457 | 0.069* | |
C17' | 0.8356 (2) | 0.85147 (18) | 0.31525 (12) | 0.0305 (5) | |
H17C | 0.7752 | 0.8800 | 0.2772 | 0.037* | |
H17D | 0.8015 | 0.7664 | 0.2952 | 0.037* | |
C18' | 0.9930 (2) | 0.8811 (2) | 0.30377 (14) | 0.0443 (6) | |
H18D | 0.9980 | 0.8455 | 0.2420 | 0.066* | |
H18E | 1.0534 | 0.8515 | 0.3400 | 0.066* | |
H18F | 1.0270 | 0.9651 | 0.3220 | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0316 (3) | 0.0309 (3) | 0.0249 (3) | 0.0009 (2) | 0.0054 (2) | 0.0110 (2) |
O1 | 0.0445 (8) | 0.0397 (9) | 0.0227 (7) | 0.0037 (7) | 0.0059 (6) | 0.0109 (7) |
O2 | 0.0314 (7) | 0.0366 (8) | 0.0390 (8) | −0.0025 (6) | 0.0063 (6) | 0.0153 (7) |
O3 | 0.0342 (7) | 0.0305 (8) | 0.0278 (7) | 0.0052 (6) | 0.0064 (6) | 0.0029 (7) |
N1 | 0.0266 (8) | 0.0268 (10) | 0.0249 (9) | −0.0003 (7) | 0.0016 (7) | 0.0071 (8) |
N2 | 0.0283 (8) | 0.0233 (9) | 0.0245 (8) | 0.0048 (7) | 0.0064 (7) | 0.0069 (7) |
C1 | 0.0323 (10) | 0.0229 (10) | 0.0241 (10) | −0.0005 (8) | 0.0027 (8) | 0.0113 (9) |
C2 | 0.0320 (11) | 0.0308 (12) | 0.0274 (11) | 0.0020 (9) | −0.0003 (9) | 0.0111 (9) |
C3 | 0.0401 (12) | 0.0313 (12) | 0.0259 (11) | 0.0053 (9) | 0.0046 (9) | 0.0097 (10) |
C4 | 0.0377 (11) | 0.0225 (11) | 0.0340 (12) | 0.0039 (9) | 0.0046 (9) | 0.0150 (10) |
C5 | 0.0301 (11) | 0.0346 (12) | 0.0383 (12) | 0.0048 (9) | −0.0028 (9) | 0.0159 (10) |
C6 | 0.0372 (11) | 0.0312 (12) | 0.0268 (11) | 0.0021 (9) | −0.0005 (9) | 0.0090 (10) |
C7 | 0.0280 (10) | 0.0261 (11) | 0.0225 (10) | 0.0079 (8) | 0.0044 (8) | 0.0052 (9) |
C8 | 0.0284 (10) | 0.0219 (10) | 0.0263 (10) | 0.0073 (8) | 0.0053 (8) | 0.0069 (9) |
C9 | 0.0367 (11) | 0.0311 (12) | 0.0254 (10) | 0.0115 (9) | 0.0082 (9) | 0.0096 (9) |
C10 | 0.0358 (11) | 0.0357 (12) | 0.0276 (11) | 0.0132 (9) | −0.0023 (9) | 0.0063 (10) |
C11 | 0.0238 (10) | 0.0357 (12) | 0.0338 (11) | 0.0071 (9) | 0.0004 (9) | 0.0055 (10) |
C12 | 0.0294 (10) | 0.0304 (11) | 0.0317 (11) | 0.0075 (9) | 0.0089 (9) | 0.0093 (10) |
C13 | 0.0403 (12) | 0.0358 (13) | 0.0450 (13) | 0.0087 (10) | 0.0081 (10) | 0.0168 (11) |
C14 | 0.0305 (10) | 0.0246 (11) | 0.0216 (10) | 0.0052 (8) | 0.0050 (8) | 0.0108 (9) |
C15 | 0.0265 (10) | 0.0307 (11) | 0.0315 (11) | 0.0053 (8) | 0.0098 (9) | 0.0108 (9) |
C16 | 0.0302 (10) | 0.0376 (12) | 0.0325 (11) | 0.0104 (9) | 0.0082 (9) | 0.0137 (10) |
C17 | 0.0333 (11) | 0.0253 (11) | 0.0313 (11) | 0.0103 (9) | 0.0095 (9) | 0.0101 (9) |
C18 | 0.0493 (13) | 0.0328 (12) | 0.0299 (11) | 0.0142 (10) | 0.0081 (10) | 0.0086 (10) |
S1' | 0.0235 (2) | 0.0323 (3) | 0.0314 (3) | 0.0011 (2) | 0.0062 (2) | 0.0119 (2) |
O1' | 0.0278 (7) | 0.0482 (9) | 0.0444 (9) | 0.0060 (7) | 0.0164 (7) | 0.0190 (8) |
O2' | 0.0335 (7) | 0.0288 (8) | 0.0369 (8) | −0.0040 (6) | 0.0007 (6) | 0.0093 (7) |
O3' | 0.0431 (8) | 0.0284 (8) | 0.0290 (8) | 0.0027 (6) | 0.0121 (7) | 0.0067 (7) |
N1' | 0.0286 (9) | 0.0247 (9) | 0.0289 (9) | 0.0024 (8) | 0.0072 (7) | 0.0090 (8) |
N2' | 0.0269 (8) | 0.0237 (9) | 0.0255 (9) | −0.0003 (7) | 0.0012 (7) | 0.0096 (7) |
C1' | 0.0190 (9) | 0.0322 (11) | 0.0278 (10) | 0.0023 (8) | 0.0008 (8) | 0.0100 (9) |
C2' | 0.0238 (10) | 0.0305 (11) | 0.0316 (11) | 0.0048 (8) | 0.0037 (9) | 0.0082 (10) |
C3' | 0.0273 (10) | 0.0388 (13) | 0.0276 (11) | 0.0041 (9) | 0.0049 (9) | 0.0119 (10) |
C4' | 0.0240 (10) | 0.0355 (12) | 0.0316 (11) | −0.0006 (9) | −0.0020 (9) | 0.0144 (10) |
C5' | 0.0406 (12) | 0.0336 (12) | 0.0381 (12) | 0.0125 (10) | 0.0042 (10) | 0.0138 (11) |
C6' | 0.0345 (11) | 0.0387 (13) | 0.0312 (11) | 0.0134 (10) | 0.0085 (9) | 0.0100 (10) |
C7' | 0.0242 (9) | 0.0288 (11) | 0.0199 (9) | 0.0034 (8) | 0.0026 (8) | 0.0095 (9) |
C8' | 0.0266 (10) | 0.0249 (11) | 0.0200 (10) | −0.0006 (8) | 0.0006 (8) | 0.0079 (9) |
C9' | 0.0262 (10) | 0.0291 (11) | 0.0264 (10) | 0.0008 (8) | 0.0035 (8) | 0.0105 (9) |
C10' | 0.0272 (10) | 0.0349 (12) | 0.0312 (11) | 0.0062 (9) | 0.0034 (9) | 0.0097 (10) |
C11' | 0.0366 (11) | 0.0260 (11) | 0.0304 (11) | 0.0069 (9) | 0.0023 (9) | 0.0090 (9) |
C12' | 0.0298 (10) | 0.0268 (11) | 0.0299 (11) | −0.0005 (8) | 0.0024 (9) | 0.0133 (9) |
C13' | 0.0447 (13) | 0.0475 (14) | 0.0386 (13) | 0.0027 (11) | 0.0016 (11) | 0.0216 (11) |
C14' | 0.0241 (10) | 0.0251 (11) | 0.0256 (10) | 0.0005 (8) | 0.0008 (8) | 0.0076 (9) |
C15' | 0.0361 (11) | 0.0240 (11) | 0.0303 (11) | −0.0016 (9) | 0.0020 (9) | 0.0092 (9) |
C16' | 0.0511 (14) | 0.0364 (13) | 0.0467 (14) | 0.0125 (11) | 0.0002 (11) | 0.0128 (11) |
C17' | 0.0304 (10) | 0.0321 (12) | 0.0246 (10) | −0.0013 (9) | 0.0012 (9) | 0.0102 (9) |
C18' | 0.0385 (12) | 0.0611 (16) | 0.0281 (11) | 0.0002 (11) | 0.0080 (10) | 0.0141 (11) |
S1—O1 | 1.4315 (13) | S1'—O2' | 1.4248 (14) |
S1—O2 | 1.4324 (13) | S1'—O1' | 1.4311 (14) |
S1—N1 | 1.6358 (17) | S1'—N1' | 1.6446 (17) |
S1—C1 | 1.758 (2) | S1'—C1' | 1.758 (2) |
O3—C14 | 1.235 (2) | O3'—C14' | 1.246 (2) |
N1—C7 | 1.435 (2) | N1'—C7' | 1.434 (2) |
N1—HN1 | 0.86 (2) | N1'—HN1' | 0.81 (2) |
N2—C14 | 1.350 (2) | N2'—C14' | 1.346 (2) |
N2—C17 | 1.469 (2) | N2'—C15' | 1.470 (2) |
N2—C15 | 1.470 (2) | N2'—C17' | 1.475 (2) |
C1—C2 | 1.388 (3) | C1'—C6' | 1.383 (3) |
C1—C6 | 1.390 (3) | C1'—C2' | 1.391 (3) |
C2—C3 | 1.381 (3) | C2'—C3' | 1.382 (3) |
C2—H2 | 0.9300 | C2'—H2' | 0.9300 |
C3—C4 | 1.395 (3) | C3'—C4' | 1.384 (3) |
C3—H3 | 0.9300 | C3'—H3' | 0.9300 |
C4—C5 | 1.386 (3) | C4'—C5' | 1.386 (3) |
C4—C13 | 1.500 (3) | C4'—C13' | 1.509 (3) |
C5—C6 | 1.384 (3) | C5'—C6' | 1.380 (3) |
C5—H5 | 0.9300 | C5'—H5' | 0.9300 |
C6—H6 | 0.9300 | C6'—H6' | 0.9300 |
C7—C12 | 1.393 (3) | C7'—C12' | 1.381 (3) |
C7—C8 | 1.400 (3) | C7'—C8' | 1.413 (2) |
C8—C9 | 1.393 (3) | C8'—C9' | 1.393 (3) |
C8—C14 | 1.493 (2) | C8'—C14' | 1.498 (3) |
C9—C10 | 1.385 (3) | C9'—C10' | 1.377 (3) |
C9—H9 | 0.9300 | C9'—H9' | 0.9300 |
C10—C11 | 1.378 (3) | C10'—C11' | 1.388 (3) |
C10—H10 | 0.9300 | C10'—H10' | 0.9300 |
C11—C12 | 1.382 (3) | C11'—C12' | 1.388 (3) |
C11—H11 | 0.9300 | C11'—H11' | 0.9300 |
C12—H12 | 0.9300 | C12'—H12' | 0.9300 |
C13—H13A | 0.9600 | C13'—H13D | 0.9600 |
C13—H13B | 0.9600 | C13'—H13E | 0.9600 |
C13—H13C | 0.9600 | C13'—H13F | 0.9600 |
C15—C16 | 1.513 (3) | C15'—C16' | 1.508 (3) |
C15—H15A | 0.9700 | C15'—H15C | 0.9700 |
C15—H15B | 0.9700 | C15'—H15D | 0.9700 |
C16—H16A | 0.9600 | C16'—H16D | 0.9600 |
C16—H16B | 0.9600 | C16'—H16E | 0.9600 |
C16—H16C | 0.9600 | C16'—H16F | 0.9600 |
C17—C18 | 1.521 (3) | C17'—C18' | 1.518 (3) |
C17—H17A | 0.9700 | C17'—H17C | 0.9700 |
C17—H17B | 0.9700 | C17'—H17D | 0.9700 |
C18—H18A | 0.9600 | C18'—H18D | 0.9600 |
C18—H18B | 0.9600 | C18'—H18E | 0.9600 |
C18—H18C | 0.9600 | C18'—H18F | 0.9600 |
O1—S1—O2 | 119.57 (8) | O2'—S1'—O1' | 120.27 (8) |
O1—S1—N1 | 105.49 (8) | O2'—S1'—N1' | 107.60 (8) |
O2—S1—N1 | 107.66 (8) | O1'—S1'—N1' | 104.98 (8) |
O1—S1—C1 | 108.16 (9) | O2'—S1'—C1' | 108.68 (9) |
O2—S1—C1 | 107.99 (9) | O1'—S1'—C1' | 107.76 (9) |
N1—S1—C1 | 107.40 (8) | N1'—S1'—C1' | 106.80 (8) |
C7—N1—S1 | 123.27 (13) | C7'—N1'—S1' | 120.56 (13) |
C7—N1—HN1 | 118.4 (13) | C7'—N1'—HN1' | 110.6 (14) |
S1—N1—HN1 | 113.0 (13) | S1'—N1'—HN1' | 110.0 (15) |
C14—N2—C17 | 124.10 (15) | C14'—N2'—C15' | 117.36 (15) |
C14—N2—C15 | 117.84 (15) | C14'—N2'—C17' | 125.41 (16) |
C17—N2—C15 | 117.24 (14) | C15'—N2'—C17' | 115.80 (15) |
C2—C1—C6 | 120.03 (18) | C6'—C1'—C2' | 120.19 (18) |
C2—C1—S1 | 119.44 (14) | C6'—C1'—S1' | 119.29 (14) |
C6—C1—S1 | 120.52 (15) | C2'—C1'—S1' | 120.51 (15) |
C3—C2—C1 | 119.89 (18) | C3'—C2'—C1' | 119.20 (19) |
C3—C2—H2 | 120.1 | C3'—C2'—H2' | 120.4 |
C1—C2—H2 | 120.1 | C1'—C2'—H2' | 120.4 |
C2—C3—C4 | 121.13 (18) | C2'—C3'—C4' | 121.49 (18) |
C2—C3—H3 | 119.4 | C2'—C3'—H3' | 119.3 |
C4—C3—H3 | 119.4 | C4'—C3'—H3' | 119.3 |
C5—C4—C3 | 117.83 (18) | C3'—C4'—C5' | 118.20 (18) |
C5—C4—C13 | 121.32 (18) | C3'—C4'—C13' | 121.76 (18) |
C3—C4—C13 | 120.85 (18) | C5'—C4'—C13' | 120.04 (19) |
C6—C5—C4 | 122.02 (18) | C6'—C5'—C4' | 121.47 (19) |
C6—C5—H5 | 119.0 | C6'—C5'—H5' | 119.3 |
C4—C5—H5 | 119.0 | C4'—C5'—H5' | 119.3 |
C5—C6—C1 | 119.07 (18) | C5'—C6'—C1' | 119.44 (18) |
C5—C6—H6 | 120.5 | C5'—C6'—H6' | 120.3 |
C1—C6—H6 | 120.5 | C1'—C6'—H6' | 120.3 |
C12—C7—C8 | 119.84 (17) | C12'—C7'—C8' | 120.49 (17) |
C12—C7—N1 | 119.24 (17) | C12'—C7'—N1' | 118.96 (16) |
C8—C7—N1 | 120.90 (16) | C8'—C7'—N1' | 120.45 (16) |
C9—C8—C7 | 118.94 (17) | C9'—C8'—C7' | 118.05 (17) |
C9—C8—C14 | 120.59 (17) | C9'—C8'—C14' | 121.72 (16) |
C7—C8—C14 | 120.36 (16) | C7'—C8'—C14' | 119.60 (16) |
C10—C9—C8 | 121.10 (18) | C10'—C9'—C8' | 121.49 (17) |
C10—C9—H9 | 119.4 | C10'—C9'—H9' | 119.3 |
C8—C9—H9 | 119.4 | C8'—C9'—H9' | 119.3 |
C11—C10—C9 | 119.21 (19) | C9'—C10'—C11' | 119.66 (18) |
C11—C10—H10 | 120.4 | C9'—C10'—H10' | 120.2 |
C9—C10—H10 | 120.4 | C11'—C10'—H10' | 120.2 |
C10—C11—C12 | 121.06 (18) | C12'—C11'—C10' | 120.24 (18) |
C10—C11—H11 | 119.5 | C12'—C11'—H11' | 119.9 |
C12—C11—H11 | 119.5 | C10'—C11'—H11' | 119.9 |
C11—C12—C7 | 119.83 (18) | C7'—C12'—C11' | 120.06 (17) |
C11—C12—H12 | 120.1 | C7'—C12'—H12' | 120.0 |
C7—C12—H12 | 120.1 | C11'—C12'—H12' | 120.0 |
C4—C13—H13A | 109.5 | C4'—C13'—H13D | 109.5 |
C4—C13—H13B | 109.5 | C4'—C13'—H13E | 109.5 |
H13A—C13—H13B | 109.5 | H13D—C13'—H13E | 109.5 |
C4—C13—H13C | 109.5 | C4'—C13'—H13F | 109.5 |
H13A—C13—H13C | 109.5 | H13D—C13'—H13F | 109.5 |
H13B—C13—H13C | 109.5 | H13E—C13'—H13F | 109.5 |
O3—C14—N2 | 122.48 (16) | O3'—C14'—N2' | 121.77 (17) |
O3—C14—C8 | 119.72 (16) | O3'—C14'—C8' | 118.54 (16) |
N2—C14—C8 | 117.80 (16) | N2'—C14'—C8' | 119.61 (16) |
N2—C15—C16 | 111.74 (15) | N2'—C15'—C16' | 113.69 (16) |
N2—C15—H15A | 109.3 | N2'—C15'—H15C | 108.8 |
C16—C15—H15A | 109.3 | C16'—C15'—H15C | 108.8 |
N2—C15—H15B | 109.3 | N2'—C15'—H15D | 108.8 |
C16—C15—H15B | 109.3 | C16'—C15'—H15D | 108.8 |
H15A—C15—H15B | 107.9 | H15C—C15'—H15D | 107.7 |
C15—C16—H16A | 109.5 | C15'—C16'—H16D | 109.5 |
C15—C16—H16B | 109.5 | C15'—C16'—H16E | 109.5 |
H16A—C16—H16B | 109.5 | H16D—C16'—H16E | 109.5 |
C15—C16—H16C | 109.5 | C15'—C16'—H16F | 109.5 |
H16A—C16—H16C | 109.5 | H16D—C16'—H16F | 109.5 |
H16B—C16—H16C | 109.5 | H16E—C16'—H16F | 109.5 |
N2—C17—C18 | 113.09 (16) | N2'—C17'—C18' | 113.74 (15) |
N2—C17—H17A | 109.0 | N2'—C17'—H17C | 108.8 |
C18—C17—H17A | 109.0 | C18'—C17'—H17C | 108.8 |
N2—C17—H17B | 109.0 | N2'—C17'—H17D | 108.8 |
C18—C17—H17B | 109.0 | C18'—C17'—H17D | 108.8 |
H17A—C17—H17B | 107.8 | H17C—C17'—H17D | 107.7 |
C17—C18—H18A | 109.5 | C17'—C18'—H18D | 109.5 |
C17—C18—H18B | 109.5 | C17'—C18'—H18E | 109.5 |
H18A—C18—H18B | 109.5 | H18D—C18'—H18E | 109.5 |
C17—C18—H18C | 109.5 | C17'—C18'—H18F | 109.5 |
H18A—C18—H18C | 109.5 | H18D—C18'—H18F | 109.5 |
H18B—C18—H18C | 109.5 | H18E—C18'—H18F | 109.5 |
C1—S1—N1—C7 | −82.2 (2) | C1'—S1'—N1'—C7' | −70.4 (2) |
HN1—N1—S1—O1 | −44 (1) | HN1'—N1'—S1'—O1' | −54 (2) |
C7—N1—S1—O2 | 33.9 (2) | C7'—N1'—S1'—O2' | 46.1 (2) |
C6—C1—S1—O1 | 11.7 (2) | C6'—C1'—S1'—O1' | 20.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1′—HN1′···O3′ | 0.81 (2) | 2.15 (2) | 2.809 (2) | 139 (2) |
N1—HN1···O3i | 0.86 (2) | 2.15 (2) | 2.969 (2) | 159 (2) |
Symmetry code: (i) −x+2, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C18H22N2O3S |
Mr | 346.43 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 9.4674 (6), 12.2882 (9), 16.0569 (12) |
α, β, γ (°) | 108.426 (7), 97.357 (6), 100.245 (6) |
V (Å3) | 1709.7 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.54 × 0.43 × 0.38 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur3 CCD diffractometer |
Absorption correction | Multi-scan (ABSPACK in CrysAlis RED; Oxford Diffraction, 2006) |
Tmin, Tmax | 0.894, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17890, 7512, 4728 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.676 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.118, 0.96 |
No. of reflections | 7512 |
No. of parameters | 441 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.42, −0.32 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SIR97 (Altomare et al., 1999), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).
C1—S1—N1—C7 | −82.2 (2) | C1'—S1'—N1'—C7' | −70.4 (2) |
HN1—N1—S1—O1 | −44 (1) | HN1'—N1'—S1'—O1' | −54 (2) |
C7—N1—S1—O2 | 33.9 (2) | C7'—N1'—S1'—O2' | 46.1 (2) |
C6—C1—S1—O1 | 11.7 (2) | C6'—C1'—S1'—O1' | 20.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1'—HN1'···O3' | 0.81 (2) | 2.15 (2) | 2.809 (2) | 139 (2) |
N1—HN1···O3i | 0.86 (2) | 2.15 (2) | 2.969 (2) | 159 (2) |
Symmetry code: (i) −x+2, −y, −z. |
Acknowledgements
The authors acknowledge the CRIST (Centro di Cristallografia Strutturale, University of Firenze), where the data collection was performed.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The sulfonamide moiety is a common pharmacophore in many biologically active compounds, such as HIV inhibitors (Lu & Tucker, 2007), antimicrobial drugs (Tappe et al., 2008), carbonic anhydrase inhibitors (Chegwidden et al., 2000), and anti-tumor agents (Purushottamachar et al., 2008). Because the structural and conformational properties of a compound usually are related to its biological properties, their study would provide useful information to design new effective drugs. In this regard, there are many recent publications reporting structural data on related sulfonamides (Parkin et al., 2008, Altamura et al., 2009, Perlovich et al., 2009, Perlovich et al., 2011,Vega-Hissi et al., 2011).
The asymmetric unit of the title compound contains two independent molecules, I and II, which are almost superimposable (Table 1). As expected, a staggered conformation about the N—S bond is adopted, with the N lone pair bisecting the OŜO angle, and with the p orbital at the ipso carbon bisecting the same angle (Table 1, Fig. 1). The sulfonamide nitrogen atom is almost planar-trigonal in molecule I (Σ<N=355 (1)°), while in II it is definitely more pyramidal (Σ<N=341 (1)°). The conformation of molecule II is stabilized by an intramolecular H-bond involving the H atom of the sulfonamide grouping (HN1') and the oxygen atom O3' of the amide moiety (Table 2). In the crystal packing, molecules I form dimers instead, which are held together by a couple of N—H···O=C hydrogen bonds (Table 2, Fig. 2). Dimers propagate along the b axis direction through π-π stacking interactions involving two symmetry related C1—C6 rings (centroid-centroid distance 3.8424 (8) Å, symmetry code: -x + 2, -y + 1, -z). No further significant intermolecular interactions are present in the crystal structure.