organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

(Received 20 November 2012; accepted 26 November 2012; online 30 November 2012)

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 sulfonamides and their derivatives and for their pharmacological applications, see: Supuran (2008[Supuran, C. T. (2008). Nat. Rev. Drug Discov. 7, 168-181.]); Turkmen et al. (2005[Turkmen, H., Durgun, M., Yılmaztekin, S., Emul, M., Innocenti, A., Vullo, D., Scozzafava, A. & Supuran, C. T. (2005). Bioorg. Med. Chem. Lett. 15, 367-372.]); Rami et al. (2011[Rami, M., Innocenti, A., Montero, J. L., Scozzafava, A., Winum, J. Y. & Supuran, C. T. (2011). Bioorg. Med. Chem. Lett. 21, 5210-5213.]). For related structures, see: Yalçın et al. (2012[Yalçın, Ş. P., Akkurt, M., Durgun, M., Türkkan, B. & Türkmen, H. (2012). Acta Cryst. E68, o3430.]); Akkurt et al. (2010a[Akkurt, M., Yalçın, Ş. P., Türkmen, H. & Büyükgüngör, O. (2010a). Acta Cryst. E66, o1596.],b[Akkurt, M., Yalçın, Ş. P., Türkmen, H. & Büyükgüngör, O. (2010b). Acta Cryst. E66, o1596.]). For puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C15H23N3O3S·H2O

  • Mr = 343.45

  • Monoclinic, P 21 /n

  • a = 11.3200 (3) Å

  • b = 7.4068 (3) Å

  • c = 20.7937 (8) Å

  • β = 96.787 (2)°

  • V = 1731.23 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.21 mm−1

  • T = 294 K

  • 0.24 × 0.15 × 0.12 mm

Data collection
  • Rigaku R-AXIS RAPID-S diffractometer

  • Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995[Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53-56.]) Tmin = 0.951, Tmax = 0.975

  • 36305 measured reflections

  • 3540 independent reflections

  • 2259 reflections with I > 2σ(I)

  • Rint = 0.166

Refinement
  • R[F2 > 2σ(F2)] = 0.073

  • wR(F2) = 0.178

  • S = 1.02

  • 3540 reflections

  • 225 parameters

  • 6 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+1, -y+1, -z; (iii) x-1, y, z; (iv) -x, -y, -z.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

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.

Related literature top

For inhibitors of carbonic anhydrase enzyme, inhibitors of cysteine protease enzyme, the antibacterial and antimicrobial activity and physical properties of sulfonamides and their derivatives and for their pharmacological applications, see: Supuran (2008); 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).

Experimental top

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.

Refinement top

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.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: 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).

Figures top
[Figure 1] 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.
[Figure 2] 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.
4-[3-(4-Methylpiperidin-1-yl)propanamido]benzenesulfonamide monohydrate top
Crystal data top
C15H23N3O3S·H2OF(000) = 736
Mr = 343.45Dx = 1.318 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5649 reflections
a = 11.3200 (3) Åθ = 2.2–26.4°
b = 7.4068 (3) ŵ = 0.21 mm1
c = 20.7937 (8) ÅT = 294 K
β = 96.787 (2)°Needle, pale yellow
V = 1731.23 (11) Å30.24 × 0.15 × 0.12 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID-S
diffractometer
3540 independent reflections
Radiation source: Sealed Tube2259 reflections with I > 2σ(I)
Graphite Monochromator monochromatorRint = 0.166
Detector resolution: 10.0000 pixels mm-1θmax = 26.4°, θmin = 2.9°
ω scansh = 1414
Absorption correction: part of the refinement model (ΔF)
(XABS2; Parkin et al., 1995)
k = 98
Tmin = 0.951, Tmax = 0.975l = 2626
36305 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178H 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 parametersΔρmax = 0.28 e Å3
6 restraintsΔρmin = 0.19 e Å3
Crystal data top
C15H23N3O3S·H2OV = 1731.23 (11) Å3
Mr = 343.45Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.3200 (3) ŵ = 0.21 mm1
b = 7.4068 (3) ÅT = 294 K
c = 20.7937 (8) Å0.24 × 0.15 × 0.12 mm
β = 96.787 (2)°
Data collection top
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 = 0.975Rint = 0.166
36305 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0736 restraints
wR(F2) = 0.178H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.28 e Å3
3540 reflectionsΔρmin = 0.19 e Å3
225 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.76956 (7)0.20104 (14)0.14854 (4)0.0554 (3)
O10.7834 (2)0.0689 (4)0.19866 (13)0.0771 (11)
O20.8487 (2)0.1984 (4)0.09984 (13)0.0704 (10)
O30.2781 (2)0.3305 (4)0.07524 (13)0.0760 (10)
N10.7847 (3)0.3954 (5)0.18229 (15)0.0626 (11)
N20.2710 (2)0.1957 (4)0.02247 (15)0.0547 (10)
N30.0921 (2)0.2718 (4)0.12766 (13)0.0488 (9)
C10.6232 (3)0.1876 (5)0.10916 (16)0.0485 (11)
C20.5308 (3)0.1398 (5)0.14342 (18)0.0567 (14)
C30.4159 (3)0.1440 (5)0.11385 (17)0.0544 (11)
C40.3907 (3)0.1938 (5)0.04939 (17)0.0486 (11)
C50.4846 (3)0.2404 (6)0.01464 (18)0.0614 (14)
C60.5994 (3)0.2372 (6)0.04540 (17)0.0603 (14)
C70.2211 (3)0.2596 (5)0.03523 (19)0.0550 (11)
C80.0882 (3)0.2390 (5)0.04644 (18)0.0598 (14)
C90.0361 (3)0.3066 (5)0.11224 (18)0.0559 (11)
C100.1611 (3)0.3832 (5)0.08670 (16)0.0539 (12)
C110.2937 (3)0.3567 (5)0.10375 (17)0.0538 (11)
C120.3345 (3)0.3988 (5)0.17425 (17)0.0555 (11)
C130.2598 (3)0.2866 (5)0.21563 (17)0.0600 (14)
C140.1277 (3)0.3160 (5)0.19643 (16)0.0569 (14)
C150.4671 (3)0.3679 (6)0.1923 (2)0.0781 (16)
O1W0.1110 (2)0.1006 (4)0.11435 (15)0.0665 (10)
H1NA0.756 (4)0.405 (6)0.2199 (13)0.0940*
H20.546400.104900.186500.0680*
H1NB0.767 (4)0.486 (4)0.1561 (18)0.0940*
H2N0.221 (3)0.161 (5)0.0497 (16)0.0820*
H30.353900.112900.137400.0650*
H50.469800.273100.028700.0740*
H60.661900.269400.022500.0720*
H8A0.053000.305300.013300.0720*
H8B0.068000.112600.042400.0720*
H9A0.049700.435600.114400.0670*
H9B0.077800.249600.145000.0670*
H10A0.141700.509400.092100.0650*
H10B0.139000.351600.041600.0650*
H11A0.335800.434300.076500.0640*
H11B0.313900.232600.094800.0640*
H120.318000.526500.181700.0670*
H13A0.278300.159800.210900.0720*
H13B0.279900.318900.260800.0720*
H14A0.083100.241100.223300.0680*
H14B0.108200.441100.204100.0680*
H15A0.486300.245200.182900.1180*
H15B0.487600.390800.237700.1180*
H15C0.511000.448100.167700.1180*
HWA0.044 (2)0.144 (5)0.115 (2)0.1000*
HWB0.109 (4)0.011 (3)0.121 (2)0.1000*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0363 (5)0.0734 (7)0.0547 (5)0.0018 (4)0.0026 (4)0.0068 (5)
O10.0563 (16)0.089 (2)0.0806 (19)0.0044 (15)0.0147 (14)0.0295 (16)
O20.0380 (13)0.107 (2)0.0673 (17)0.0088 (14)0.0107 (12)0.0009 (15)
O30.0451 (15)0.109 (2)0.0711 (18)0.0076 (14)0.0051 (13)0.0250 (17)
N10.0512 (18)0.081 (2)0.054 (2)0.0091 (17)0.0008 (15)0.0017 (18)
N20.0377 (15)0.069 (2)0.0554 (18)0.0023 (15)0.0034 (13)0.0039 (16)
N30.0367 (14)0.0587 (18)0.0497 (16)0.0001 (13)0.0000 (12)0.0014 (14)
C10.0325 (16)0.059 (2)0.053 (2)0.0016 (15)0.0013 (14)0.0013 (17)
C20.045 (2)0.072 (3)0.052 (2)0.0018 (17)0.0017 (16)0.0059 (18)
C30.0368 (18)0.071 (2)0.055 (2)0.0057 (16)0.0043 (15)0.0054 (18)
C40.0366 (17)0.054 (2)0.054 (2)0.0007 (15)0.0002 (15)0.0005 (16)
C50.0390 (19)0.094 (3)0.050 (2)0.0023 (18)0.0004 (16)0.0091 (19)
C60.0392 (19)0.092 (3)0.050 (2)0.0019 (18)0.0061 (16)0.007 (2)
C70.0412 (19)0.058 (2)0.064 (2)0.0029 (16)0.0013 (17)0.0011 (19)
C80.0396 (19)0.073 (3)0.064 (2)0.0046 (17)0.0061 (17)0.0003 (19)
C90.0381 (18)0.066 (2)0.062 (2)0.0012 (16)0.0011 (16)0.0053 (19)
C100.050 (2)0.062 (2)0.048 (2)0.0020 (17)0.0018 (16)0.0053 (17)
C110.0415 (18)0.061 (2)0.059 (2)0.0008 (16)0.0059 (16)0.0015 (18)
C120.0444 (19)0.061 (2)0.058 (2)0.0043 (17)0.0066 (16)0.0040 (18)
C130.053 (2)0.074 (3)0.050 (2)0.0034 (19)0.0063 (17)0.0028 (18)
C140.052 (2)0.074 (3)0.0439 (19)0.0041 (18)0.0025 (16)0.0021 (18)
C150.043 (2)0.095 (3)0.092 (3)0.003 (2)0.010 (2)0.007 (3)
O1W0.0476 (14)0.0696 (18)0.0827 (19)0.0055 (13)0.0089 (14)0.0065 (16)
Geometric parameters (Å, º) top
S1—O11.425 (3)C11—C121.516 (5)
S1—O21.429 (3)C12—C151.521 (5)
S1—N11.602 (4)C12—C131.523 (5)
S1—C11.762 (3)C13—C141.517 (5)
O3—C71.229 (5)C2—H20.9300
O1W—HWA0.83 (3)C3—H30.9300
O1W—HWB0.84 (2)C5—H50.9300
N2—C41.404 (4)C6—H60.9300
N2—C71.350 (5)C8—H8A0.9700
N3—C91.472 (4)C8—H8B0.9700
N3—C141.476 (4)C9—H9A0.9700
N3—C101.474 (4)C9—H9B0.9700
N1—H1NA0.88 (3)C10—H10B0.9700
N1—H1NB0.87 (3)C10—H10A0.9700
N2—H2N0.89 (3)C11—H11A0.9700
C1—C21.380 (5)C11—H11B0.9700
C1—C61.372 (5)C12—H120.9800
C2—C31.372 (5)C13—H13B0.9700
C3—C41.387 (5)C13—H13A0.9700
C4—C51.397 (5)C14—H14B0.9700
C5—C61.379 (5)C14—H14A0.9700
C7—C81.503 (5)C15—H15C0.9600
C8—C91.510 (5)C15—H15A0.9600
C10—C111.514 (5)C15—H15B0.9600
O1—S1—O2119.01 (16)C6—C5—H5120.00
O1—S1—N1107.46 (17)C5—C6—H6119.00
O1—S1—C1108.49 (16)C1—C6—H6119.00
O2—S1—N1106.21 (18)C7—C8—H8A109.00
O2—S1—C1107.68 (16)C9—C8—H8A109.00
N1—S1—C1107.48 (18)C9—C8—H8B109.00
HWA—O1W—HWB110 (4)H8A—C8—H8B108.00
C4—N2—C7129.9 (3)C7—C8—H8B109.00
C9—N3—C14108.8 (3)N3—C9—H9B109.00
C10—N3—C14109.5 (3)C8—C9—H9A109.00
C9—N3—C10110.6 (3)N3—C9—H9A109.00
S1—N1—H1NA115 (3)H9A—C9—H9B108.00
H1NA—N1—H1NB114 (4)C8—C9—H9B109.00
S1—N1—H1NB114 (2)N3—C10—H10B109.00
C4—N2—H2N114 (2)C11—C10—H10A109.00
C7—N2—H2N116 (2)C11—C10—H10B109.00
C2—C1—C6119.6 (3)H10A—C10—H10B108.00
S1—C1—C2120.2 (3)N3—C10—H10A109.00
S1—C1—C6120.0 (3)C10—C11—H11A109.00
C1—C2—C3120.0 (3)C10—C11—H11B109.00
C2—C3—C4121.0 (3)C12—C11—H11B109.00
N2—C4—C5123.3 (3)H11A—C11—H11B108.00
N2—C4—C3117.8 (3)C12—C11—H11A109.00
C3—C4—C5118.9 (3)C11—C12—H12108.00
C4—C5—C6119.3 (3)C15—C12—H12108.00
C1—C6—C5121.3 (3)C13—C12—H12108.00
O3—C7—C8122.3 (3)C12—C13—H13A109.00
O3—C7—N2123.6 (3)C14—C13—H13A109.00
N2—C7—C8114.1 (3)C14—C13—H13B109.00
C7—C8—C9112.6 (3)H13A—C13—H13B108.00
N3—C9—C8114.1 (3)C12—C13—H13B109.00
N3—C10—C11111.8 (3)N3—C14—H14A109.00
C10—C11—C12112.3 (3)C13—C14—H14A109.00
C13—C12—C15112.1 (3)C13—C14—H14B109.00
C11—C12—C13107.9 (3)N3—C14—H14B109.00
C11—C12—C15112.7 (3)H14A—C14—H14B108.00
C12—C13—C14111.7 (3)C12—C15—H15B109.00
N3—C14—C13111.8 (3)C12—C15—H15C109.00
C1—C2—H2120.00C12—C15—H15A109.00
C3—C2—H2120.00H15A—C15—H15C109.00
C4—C3—H3119.00H15B—C15—H15C110.00
C2—C3—H3120.00H15A—C15—H15B109.00
C4—C5—H5120.00
O1—S1—C1—C232.8 (4)S1—C1—C6—C5175.3 (3)
O2—S1—C1—C2162.8 (3)S1—C1—C2—C3174.6 (3)
N1—S1—C1—C283.2 (3)C1—C2—C3—C40.8 (6)
O1—S1—C1—C6151.9 (3)C2—C3—C4—N2179.7 (3)
O2—S1—C1—C621.9 (4)C2—C3—C4—C50.1 (6)
N1—S1—C1—C692.2 (3)N2—C4—C5—C6179.0 (4)
C7—N2—C4—C3170.6 (4)C3—C4—C5—C60.6 (6)
C7—N2—C4—C59.1 (6)C4—C5—C6—C10.6 (6)
C4—N2—C7—O30.0 (6)N2—C7—C8—C9178.2 (3)
C4—N2—C7—C8179.3 (3)O3—C7—C8—C92.5 (5)
C9—N3—C10—C11177.3 (3)C7—C8—C9—N3174.1 (3)
C10—N3—C9—C869.1 (4)N3—C10—C11—C1257.4 (4)
C14—N3—C9—C8170.7 (3)C10—C11—C12—C15178.5 (3)
C10—N3—C14—C1358.0 (4)C10—C11—C12—C1354.1 (4)
C14—N3—C10—C1157.5 (4)C11—C12—C13—C1454.3 (4)
C9—N3—C14—C13179.0 (3)C15—C12—C13—C14179.0 (3)
C6—C1—C2—C30.7 (6)C12—C13—C14—N358.0 (4)
C2—C1—C6—C50.0 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1NA···O1i0.88 (3)2.17 (4)2.971 (4)150 (4)
N1—H1NB···O3ii0.87 (3)2.18 (3)3.035 (4)168 (3)
N2—H2N···O1W0.89 (3)1.99 (3)2.871 (4)176 (3)
O1W—HWA···O2iii0.83 (3)2.23 (2)3.037 (3)165 (4)
O1W—HWB···N3iv0.84 (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) x1, y, z; (iv) x, y, z.

Experimental details

Crystal data
Chemical formulaC15H23N3O3S·H2O
Mr343.45
Crystal system, space groupMonoclinic, P21/n
Temperature (K)294
a, b, c (Å)11.3200 (3), 7.4068 (3), 20.7937 (8)
β (°) 96.787 (2)
V3)1731.23 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.24 × 0.15 × 0.12
Data collection
DiffractometerRigaku R-AXIS RAPID-S
diffractometer
Absorption correctionPart of the refinement model (ΔF)
(XABS2; Parkin et al., 1995)
Tmin, Tmax0.951, 0.975
No. of measured, independent and
observed [I > 2σ(I)] reflections
36305, 3540, 2259
Rint0.166
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.073, 0.178, 1.02
No. of reflections3540
No. of parameters225
No. of restraints6
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1NA···O1i0.88 (3)2.17 (4)2.971 (4)150 (4)
N1—H1NB···O3ii0.87 (3)2.18 (3)3.035 (4)168 (3)
N2—H2N···O1W0.89 (3)1.99 (3)2.871 (4)176 (3)
O1W—HWA···O2iii0.83 (3)2.23 (2)3.037 (3)165 (4)
O1W—HWB···N3iv0.84 (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) x1, 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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