organic compounds
4-[3-(4-Methylpiperidin-1-yl)propanamido]benzenesulfonamide monohydrate
aDepartment of Chemistry, Faculty of Arts and Sciences, Harran University, 63300 Şanlıurfa, Turkey, bDepartment of Physics, Faculty of Arts and Sciences, Harran University, 63300 Şanlıurfa, Turkey, cCentral Research Lab, Harran University, Osmanbey Campus, 63300 Şanlıurfa, Turkey, and dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr
In the title compound, C15H23N3O3S·H2O, the piperidine ring has a chair conformation. In the crystal, the sulfonamide molecules are linked by N—H⋯O hydrogen bonds, forming a layer parallel to (10-1). The layers are interconnected via N—H⋯Ow, Ow—H⋯N and Ow—H⋯O (w = water) hydrogen bonds, forming a three-dimensional network.
Related literature
For inhibitors of carbonic anhydrase enzyme, inhibitors of cysteine protease enzyme, the antibacterial and antimicrobial activity and physical properties of ); Turkmen et al. (2005); Rami et al. (2011). For related structures, see: Yalçın et al. (2012); Akkurt et al. (2010a,b). For puckering analysis, see: Cremer & Pople (1975).
and their derivatives and for their pharmacological applications, see: Supuran (2008Experimental
Crystal data
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Refinement
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Data collection: CrystalClear (Rigaku/MSC, 2005); cell CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812048477/is5222sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812048477/is5222Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812048477/is5222Isup3.cml
The starting material, 4-(3-chloropropionylamino)benzenesulfonamide, was prepared by the reaction of sulfanilamide with 3-chloropropanoylchloride (Turkmen et al., 2005). The title compound, 4-(3-methylpiperidinopropionylamino)benzenesulfonamide was prepared by the reaction of 4-(3-chloropropionylamino)benzenesulfonamide with 3-methylpiperidine (Turkmen et al., 2005). To a stirred solution of an excess of 3-methylpiperidine (1.12 g, 11.4 mmol) and TEA (1.75 g, 7.6 mmol) in tetrahydrofuran (20 ml) was added 4-(3-chloropropionylamino)benzenesulfonamide (1.00 g, 3.80 mmol) over 30 min at 273 K. After completion of the addition the reaction was allowed to warm to room temperature and stirred at 313 K for 48 h. The impurity was removed by flash column chromotography (ethyl acetate/methanol: 6/1) to give the title compound. (70%), m.p. 435–437 K; Anal. Calculated for C15H23N2O3S (%): C 55.36, H 7.12, N 12.91, S 9.85. Found (%): C 55.17, H 7.44, N 12.7, S 9.43; (KBr, υmax/cm-1) 1682 (NHCO), 1181 (SO2NH2); dH(DMSO-d6) 11.83 (1H, s, –CONH), 7.85 (4H, m, –Ar—H), 7.2 (2H, s, SO2NH2), 2.72 (2H, t, J 6 Hz, –NCH2), 2.55 (2H, t, J 6 Hz, CH2CO), 2.24 (4H, t, J 6 Hz, CH2NCH2), 1.67 (H, s, CH3CH), 1.48 (4H, t, J 6 Hz, CH2CHCH2), 1.01 (3H, s, CH3–); dC(DMSO-d6) 173.28 (C=O), 144.83 (CNH–),138.24 (C—SO2NH2), 128.7 (C-2 Aryl), 128.7 (C-2 Aryl), 121.18 (C-3 Aryl), 121.18 (C-3 Aryl), 55.7(CH2N–), 54.97 (CH2NCH2), 38.8 (CH2CO), 34.72 (CH2CHCH2), 32.04 (CH2CHCH2), 23.01 (CH3N–); m/z EI+ 327 [M]+. Crystals suitable for X-ray diffraction studies were grown by slow evaporation of an ethanol, chloroform, dichloromethane (4/3/3 v/v) solution of 4-(3-methylpiperidinopropionylamino)benzenesulfonamide.
The H atoms of the NH and NH2 groups and the water molecule were located from a difference Fourier map and refined with distance restraints of N—H = 0.88 (2) Å and O—H = 0.83 (2), H···H = 1.35 Å, and with Uiso(H) = 1.5Ueq(N,O). The rest H atoms were positioned geometrically, with C—H = 0.93–0.97 Å, and refined as riding with Uiso(H) = 1.2 or 1.5Ueq(C). Seven poorly fitted reflections (4 0 10), (-4 1 20), (-1 0 2), (3 0 14), (-5 5 15), (-6 1 23) and (0 5 6) were omitted from the refinement.
Data collection: CrystalClear (Rigaku/MSC, 2005); cell
CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title molecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. | |
Fig. 2. View of the packing and hydrogen bonds of the title compound down the a axis. H atoms not involved in the hydrogen bonds have been omitted for clarity. |
C15H23N3O3S·H2O | F(000) = 736 |
Mr = 343.45 | Dx = 1.318 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5649 reflections |
a = 11.3200 (3) Å | θ = 2.2–26.4° |
b = 7.4068 (3) Å | µ = 0.21 mm−1 |
c = 20.7937 (8) Å | T = 294 K |
β = 96.787 (2)° | Needle, pale yellow |
V = 1731.23 (11) Å3 | 0.24 × 0.15 × 0.12 mm |
Z = 4 |
Rigaku R-AXIS RAPID-S diffractometer | 3540 independent reflections |
Radiation source: Sealed Tube | 2259 reflections with I > 2σ(I) |
Graphite Monochromator monochromator | Rint = 0.166 |
Detector resolution: 10.0000 pixels mm-1 | θmax = 26.4°, θmin = 2.9° |
ω scans | h = −14→14 |
Absorption correction: part of the (XABS2; Parkin et al., 1995) | model (ΔF) k = −9→8 |
Tmin = 0.951, Tmax = 0.975 | l = −26→26 |
36305 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)] = 0.073 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.178 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0595P)2 + 1.0901P] where P = (Fo2 + 2Fc2)/3 |
3540 reflections | (Δ/σ)max < 0.001 |
225 parameters | Δρmax = 0.28 e Å−3 |
6 restraints | Δρmin = −0.19 e Å−3 |
C15H23N3O3S·H2O | V = 1731.23 (11) Å3 |
Mr = 343.45 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.3200 (3) Å | µ = 0.21 mm−1 |
b = 7.4068 (3) Å | T = 294 K |
c = 20.7937 (8) Å | 0.24 × 0.15 × 0.12 mm |
β = 96.787 (2)° |
Rigaku R-AXIS RAPID-S diffractometer | 3540 independent reflections |
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995) | 2259 reflections with I > 2σ(I) |
Tmin = 0.951, Tmax = 0.975 | Rint = 0.166 |
36305 measured reflections |
R[F2 > 2σ(F2)] = 0.073 | 6 restraints |
wR(F2) = 0.178 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.28 e Å−3 |
3540 reflections | Δρmin = −0.19 e Å−3 |
225 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | 0.76956 (7) | 0.20104 (14) | 0.14854 (4) | 0.0554 (3) | |
O1 | 0.7834 (2) | 0.0689 (4) | 0.19866 (13) | 0.0771 (11) | |
O2 | 0.8487 (2) | 0.1984 (4) | 0.09984 (13) | 0.0704 (10) | |
O3 | 0.2781 (2) | 0.3305 (4) | −0.07524 (13) | 0.0760 (10) | |
N1 | 0.7847 (3) | 0.3954 (5) | 0.18229 (15) | 0.0626 (11) | |
N2 | 0.2710 (2) | 0.1957 (4) | 0.02247 (15) | 0.0547 (10) | |
N3 | −0.0921 (2) | 0.2718 (4) | −0.12766 (13) | 0.0488 (9) | |
C1 | 0.6232 (3) | 0.1876 (5) | 0.10916 (16) | 0.0485 (11) | |
C2 | 0.5308 (3) | 0.1398 (5) | 0.14342 (18) | 0.0567 (14) | |
C3 | 0.4159 (3) | 0.1440 (5) | 0.11385 (17) | 0.0544 (11) | |
C4 | 0.3907 (3) | 0.1938 (5) | 0.04939 (17) | 0.0486 (11) | |
C5 | 0.4846 (3) | 0.2404 (6) | 0.01464 (18) | 0.0614 (14) | |
C6 | 0.5994 (3) | 0.2372 (6) | 0.04540 (17) | 0.0603 (14) | |
C7 | 0.2211 (3) | 0.2596 (5) | −0.03523 (19) | 0.0550 (11) | |
C8 | 0.0882 (3) | 0.2390 (5) | −0.04644 (18) | 0.0598 (14) | |
C9 | 0.0361 (3) | 0.3066 (5) | −0.11224 (18) | 0.0559 (11) | |
C10 | −0.1611 (3) | 0.3832 (5) | −0.08670 (16) | 0.0539 (12) | |
C11 | −0.2937 (3) | 0.3567 (5) | −0.10375 (17) | 0.0538 (11) | |
C12 | −0.3345 (3) | 0.3988 (5) | −0.17425 (17) | 0.0555 (11) | |
C13 | −0.2598 (3) | 0.2866 (5) | −0.21563 (17) | 0.0600 (14) | |
C14 | −0.1277 (3) | 0.3160 (5) | −0.19643 (16) | 0.0569 (14) | |
C15 | −0.4671 (3) | 0.3679 (6) | −0.1923 (2) | 0.0781 (16) | |
O1W | 0.1110 (2) | 0.1006 (4) | 0.11435 (15) | 0.0665 (10) | |
H1NA | 0.756 (4) | 0.405 (6) | 0.2199 (13) | 0.0940* | |
H2 | 0.54640 | 0.10490 | 0.18650 | 0.0680* | |
H1NB | 0.767 (4) | 0.486 (4) | 0.1561 (18) | 0.0940* | |
H2N | 0.221 (3) | 0.161 (5) | 0.0497 (16) | 0.0820* | |
H3 | 0.35390 | 0.11290 | 0.13740 | 0.0650* | |
H5 | 0.46980 | 0.27310 | −0.02870 | 0.0740* | |
H6 | 0.66190 | 0.26940 | 0.02250 | 0.0720* | |
H8A | 0.05300 | 0.30530 | −0.01330 | 0.0720* | |
H8B | 0.06800 | 0.11260 | −0.04240 | 0.0720* | |
H9A | 0.04970 | 0.43560 | −0.11440 | 0.0670* | |
H9B | 0.07780 | 0.24960 | −0.14500 | 0.0670* | |
H10A | −0.14170 | 0.50940 | −0.09210 | 0.0650* | |
H10B | −0.13900 | 0.35160 | −0.04160 | 0.0650* | |
H11A | −0.33580 | 0.43430 | −0.07650 | 0.0640* | |
H11B | −0.31390 | 0.23260 | −0.09480 | 0.0640* | |
H12 | −0.31800 | 0.52650 | −0.18170 | 0.0670* | |
H13A | −0.27830 | 0.15980 | −0.21090 | 0.0720* | |
H13B | −0.27990 | 0.31890 | −0.26080 | 0.0720* | |
H14A | −0.08310 | 0.24110 | −0.22330 | 0.0680* | |
H14B | −0.10820 | 0.44110 | −0.20410 | 0.0680* | |
H15A | −0.48630 | 0.24520 | −0.18290 | 0.1180* | |
H15B | −0.48760 | 0.39080 | −0.23770 | 0.1180* | |
H15C | −0.51100 | 0.44810 | −0.16770 | 0.1180* | |
HWA | 0.044 (2) | 0.144 (5) | 0.115 (2) | 0.1000* | |
HWB | 0.109 (4) | −0.011 (3) | 0.121 (2) | 0.1000* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0363 (5) | 0.0734 (7) | 0.0547 (5) | 0.0018 (4) | −0.0026 (4) | 0.0068 (5) |
O1 | 0.0563 (16) | 0.089 (2) | 0.0806 (19) | −0.0044 (15) | −0.0147 (14) | 0.0295 (16) |
O2 | 0.0380 (13) | 0.107 (2) | 0.0673 (17) | 0.0088 (14) | 0.0107 (12) | −0.0009 (15) |
O3 | 0.0451 (15) | 0.109 (2) | 0.0711 (18) | −0.0076 (14) | −0.0051 (13) | 0.0250 (17) |
N1 | 0.0512 (18) | 0.081 (2) | 0.054 (2) | −0.0091 (17) | −0.0008 (15) | −0.0017 (18) |
N2 | 0.0377 (15) | 0.069 (2) | 0.0554 (18) | −0.0023 (15) | −0.0034 (13) | 0.0039 (16) |
N3 | 0.0367 (14) | 0.0587 (18) | 0.0497 (16) | −0.0001 (13) | 0.0000 (12) | −0.0014 (14) |
C1 | 0.0325 (16) | 0.059 (2) | 0.053 (2) | 0.0016 (15) | 0.0013 (14) | 0.0013 (17) |
C2 | 0.045 (2) | 0.072 (3) | 0.052 (2) | −0.0018 (17) | 0.0017 (16) | 0.0059 (18) |
C3 | 0.0368 (18) | 0.071 (2) | 0.055 (2) | −0.0057 (16) | 0.0043 (15) | 0.0054 (18) |
C4 | 0.0366 (17) | 0.054 (2) | 0.054 (2) | −0.0007 (15) | 0.0002 (15) | −0.0005 (16) |
C5 | 0.0390 (19) | 0.094 (3) | 0.050 (2) | −0.0023 (18) | 0.0004 (16) | 0.0091 (19) |
C6 | 0.0392 (19) | 0.092 (3) | 0.050 (2) | −0.0019 (18) | 0.0061 (16) | 0.007 (2) |
C7 | 0.0412 (19) | 0.058 (2) | 0.064 (2) | −0.0029 (16) | −0.0013 (17) | −0.0011 (19) |
C8 | 0.0396 (19) | 0.073 (3) | 0.064 (2) | −0.0046 (17) | −0.0061 (17) | −0.0003 (19) |
C9 | 0.0381 (18) | 0.066 (2) | 0.062 (2) | −0.0012 (16) | −0.0011 (16) | 0.0053 (19) |
C10 | 0.050 (2) | 0.062 (2) | 0.048 (2) | 0.0020 (17) | −0.0018 (16) | −0.0053 (17) |
C11 | 0.0415 (18) | 0.061 (2) | 0.059 (2) | 0.0008 (16) | 0.0059 (16) | −0.0015 (18) |
C12 | 0.0444 (19) | 0.061 (2) | 0.058 (2) | 0.0043 (17) | −0.0066 (16) | 0.0040 (18) |
C13 | 0.053 (2) | 0.074 (3) | 0.050 (2) | 0.0034 (19) | −0.0063 (17) | 0.0028 (18) |
C14 | 0.052 (2) | 0.074 (3) | 0.0439 (19) | 0.0041 (18) | 0.0025 (16) | 0.0021 (18) |
C15 | 0.043 (2) | 0.095 (3) | 0.092 (3) | 0.003 (2) | −0.010 (2) | 0.007 (3) |
O1W | 0.0476 (14) | 0.0696 (18) | 0.0827 (19) | −0.0055 (13) | 0.0089 (14) | 0.0065 (16) |
S1—O1 | 1.425 (3) | C11—C12 | 1.516 (5) |
S1—O2 | 1.429 (3) | C12—C15 | 1.521 (5) |
S1—N1 | 1.602 (4) | C12—C13 | 1.523 (5) |
S1—C1 | 1.762 (3) | C13—C14 | 1.517 (5) |
O3—C7 | 1.229 (5) | C2—H2 | 0.9300 |
O1W—HWA | 0.83 (3) | C3—H3 | 0.9300 |
O1W—HWB | 0.84 (2) | C5—H5 | 0.9300 |
N2—C4 | 1.404 (4) | C6—H6 | 0.9300 |
N2—C7 | 1.350 (5) | C8—H8A | 0.9700 |
N3—C9 | 1.472 (4) | C8—H8B | 0.9700 |
N3—C14 | 1.476 (4) | C9—H9A | 0.9700 |
N3—C10 | 1.474 (4) | C9—H9B | 0.9700 |
N1—H1NA | 0.88 (3) | C10—H10B | 0.9700 |
N1—H1NB | 0.87 (3) | C10—H10A | 0.9700 |
N2—H2N | 0.89 (3) | C11—H11A | 0.9700 |
C1—C2 | 1.380 (5) | C11—H11B | 0.9700 |
C1—C6 | 1.372 (5) | C12—H12 | 0.9800 |
C2—C3 | 1.372 (5) | C13—H13B | 0.9700 |
C3—C4 | 1.387 (5) | C13—H13A | 0.9700 |
C4—C5 | 1.397 (5) | C14—H14B | 0.9700 |
C5—C6 | 1.379 (5) | C14—H14A | 0.9700 |
C7—C8 | 1.503 (5) | C15—H15C | 0.9600 |
C8—C9 | 1.510 (5) | C15—H15A | 0.9600 |
C10—C11 | 1.514 (5) | C15—H15B | 0.9600 |
O1—S1—O2 | 119.01 (16) | C6—C5—H5 | 120.00 |
O1—S1—N1 | 107.46 (17) | C5—C6—H6 | 119.00 |
O1—S1—C1 | 108.49 (16) | C1—C6—H6 | 119.00 |
O2—S1—N1 | 106.21 (18) | C7—C8—H8A | 109.00 |
O2—S1—C1 | 107.68 (16) | C9—C8—H8A | 109.00 |
N1—S1—C1 | 107.48 (18) | C9—C8—H8B | 109.00 |
HWA—O1W—HWB | 110 (4) | H8A—C8—H8B | 108.00 |
C4—N2—C7 | 129.9 (3) | C7—C8—H8B | 109.00 |
C9—N3—C14 | 108.8 (3) | N3—C9—H9B | 109.00 |
C10—N3—C14 | 109.5 (3) | C8—C9—H9A | 109.00 |
C9—N3—C10 | 110.6 (3) | N3—C9—H9A | 109.00 |
S1—N1—H1NA | 115 (3) | H9A—C9—H9B | 108.00 |
H1NA—N1—H1NB | 114 (4) | C8—C9—H9B | 109.00 |
S1—N1—H1NB | 114 (2) | N3—C10—H10B | 109.00 |
C4—N2—H2N | 114 (2) | C11—C10—H10A | 109.00 |
C7—N2—H2N | 116 (2) | C11—C10—H10B | 109.00 |
C2—C1—C6 | 119.6 (3) | H10A—C10—H10B | 108.00 |
S1—C1—C2 | 120.2 (3) | N3—C10—H10A | 109.00 |
S1—C1—C6 | 120.0 (3) | C10—C11—H11A | 109.00 |
C1—C2—C3 | 120.0 (3) | C10—C11—H11B | 109.00 |
C2—C3—C4 | 121.0 (3) | C12—C11—H11B | 109.00 |
N2—C4—C5 | 123.3 (3) | H11A—C11—H11B | 108.00 |
N2—C4—C3 | 117.8 (3) | C12—C11—H11A | 109.00 |
C3—C4—C5 | 118.9 (3) | C11—C12—H12 | 108.00 |
C4—C5—C6 | 119.3 (3) | C15—C12—H12 | 108.00 |
C1—C6—C5 | 121.3 (3) | C13—C12—H12 | 108.00 |
O3—C7—C8 | 122.3 (3) | C12—C13—H13A | 109.00 |
O3—C7—N2 | 123.6 (3) | C14—C13—H13A | 109.00 |
N2—C7—C8 | 114.1 (3) | C14—C13—H13B | 109.00 |
C7—C8—C9 | 112.6 (3) | H13A—C13—H13B | 108.00 |
N3—C9—C8 | 114.1 (3) | C12—C13—H13B | 109.00 |
N3—C10—C11 | 111.8 (3) | N3—C14—H14A | 109.00 |
C10—C11—C12 | 112.3 (3) | C13—C14—H14A | 109.00 |
C13—C12—C15 | 112.1 (3) | C13—C14—H14B | 109.00 |
C11—C12—C13 | 107.9 (3) | N3—C14—H14B | 109.00 |
C11—C12—C15 | 112.7 (3) | H14A—C14—H14B | 108.00 |
C12—C13—C14 | 111.7 (3) | C12—C15—H15B | 109.00 |
N3—C14—C13 | 111.8 (3) | C12—C15—H15C | 109.00 |
C1—C2—H2 | 120.00 | C12—C15—H15A | 109.00 |
C3—C2—H2 | 120.00 | H15A—C15—H15C | 109.00 |
C4—C3—H3 | 119.00 | H15B—C15—H15C | 110.00 |
C2—C3—H3 | 120.00 | H15A—C15—H15B | 109.00 |
C4—C5—H5 | 120.00 | ||
O1—S1—C1—C2 | 32.8 (4) | S1—C1—C6—C5 | −175.3 (3) |
O2—S1—C1—C2 | 162.8 (3) | S1—C1—C2—C3 | 174.6 (3) |
N1—S1—C1—C2 | −83.2 (3) | C1—C2—C3—C4 | 0.8 (6) |
O1—S1—C1—C6 | −151.9 (3) | C2—C3—C4—N2 | −179.7 (3) |
O2—S1—C1—C6 | −21.9 (4) | C2—C3—C4—C5 | −0.1 (6) |
N1—S1—C1—C6 | 92.2 (3) | N2—C4—C5—C6 | 179.0 (4) |
C7—N2—C4—C3 | 170.6 (4) | C3—C4—C5—C6 | −0.6 (6) |
C7—N2—C4—C5 | −9.1 (6) | C4—C5—C6—C1 | 0.6 (6) |
C4—N2—C7—O3 | 0.0 (6) | N2—C7—C8—C9 | −178.2 (3) |
C4—N2—C7—C8 | −179.3 (3) | O3—C7—C8—C9 | 2.5 (5) |
C9—N3—C10—C11 | 177.3 (3) | C7—C8—C9—N3 | 174.1 (3) |
C10—N3—C9—C8 | 69.1 (4) | N3—C10—C11—C12 | −57.4 (4) |
C14—N3—C9—C8 | −170.7 (3) | C10—C11—C12—C15 | 178.5 (3) |
C10—N3—C14—C13 | −58.0 (4) | C10—C11—C12—C13 | 54.1 (4) |
C14—N3—C10—C11 | 57.5 (4) | C11—C12—C13—C14 | −54.3 (4) |
C9—N3—C14—C13 | −179.0 (3) | C15—C12—C13—C14 | −179.0 (3) |
C6—C1—C2—C3 | −0.7 (6) | C12—C13—C14—N3 | 58.0 (4) |
C2—C1—C6—C5 | 0.0 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1NA···O1i | 0.88 (3) | 2.17 (4) | 2.971 (4) | 150 (4) |
N1—H1NB···O3ii | 0.87 (3) | 2.18 (3) | 3.035 (4) | 168 (3) |
N2—H2N···O1W | 0.89 (3) | 1.99 (3) | 2.871 (4) | 176 (3) |
O1W—HWA···O2iii | 0.83 (3) | 2.23 (2) | 3.037 (3) | 165 (4) |
O1W—HWB···N3iv | 0.84 (2) | 1.95 (2) | 2.783 (4) | 174 (5) |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) x−1, y, z; (iv) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C15H23N3O3S·H2O |
Mr | 343.45 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 294 |
a, b, c (Å) | 11.3200 (3), 7.4068 (3), 20.7937 (8) |
β (°) | 96.787 (2) |
V (Å3) | 1731.23 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.24 × 0.15 × 0.12 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID-S diffractometer |
Absorption correction | Part of the refinement model (ΔF) (XABS2; Parkin et al., 1995) |
Tmin, Tmax | 0.951, 0.975 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 36305, 3540, 2259 |
Rint | 0.166 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.073, 0.178, 1.02 |
No. of reflections | 3540 |
No. of parameters | 225 |
No. of restraints | 6 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.28, −0.19 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1NA···O1i | 0.88 (3) | 2.17 (4) | 2.971 (4) | 150 (4) |
N1—H1NB···O3ii | 0.87 (3) | 2.18 (3) | 3.035 (4) | 168 (3) |
N2—H2N···O1W | 0.89 (3) | 1.99 (3) | 2.871 (4) | 176 (3) |
O1W—HWA···O2iii | 0.83 (3) | 2.23 (2) | 3.037 (3) | 165 (4) |
O1W—HWB···N3iv | 0.84 (2) | 1.95 (2) | 2.783 (4) | 174 (5) |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z; (iii) x−1, y, z; (iv) −x, −y, −z. |
Acknowledgements
The authors thank the Unit of Scientific Research Projects of Harran University, Turkey for a research grant (HUBAK project Nos. 348 and 1136).
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.
Sulfonamides have been used as therapeutic agents for over fifty years. The basic sulfonamide group –SO2NH– occurs in various biological active compounds including antimicrobial drugs, antithyroid agents, antitumor, antibiotics and inhibitors of carbonic anhydrase (Rami et al., 2011; Supuran, 2008; Turkmen et al., 2005). In the present study, we have prepared and determined the crystal structure of the 4-(3-methylpiperidinopropionylamino)-benzenesulfonamide.
In the title compound (Fig. 1), the piperidine ring has a chair conformation, with the puckering parameters (Cremer & Pople, 1975) of QT = 0.571 (4) Å, θ = 180.0 (4)° and ϕ = 150 (19)°. The O3—C7—N2—C4, O3—C7—C8—C9, N2—C7—C8—C9 and C7—C8—C9—N3 torsion angles are -0.0 (6), 2.5 (5), -178.2 (3) and 174.1 (3)°, respectively. The bond lengths and bond angles are within the normal range and are comparable to those previously reported for the related similar structures (Pınar Yalçın et al., 2012; Akkurt et al., 2010a,b). The crystal structure is stabilized by intermolecular N—H···O, N—H···Owater, Owater—H···N and Owater—H···O hydrogen bonds (Table 1 and Fig. 2), forming a three dimensional network.