4-[3-(4-Methyl-piperidin-1-yl)propan-amido]-benzene-sulfonamide monohydrate.

In the title compound, C15H23N3O3S·H2O, the piperidine ring has a chair conformation. In the crystal, the sulfonamide mol-ecules are linked by N-H⋯O hydrogen bonds, forming a layer parallel to (10-1). The layers are inter-connected 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 ▶); 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

Crystal data

C15H23N3O3S·H2O

M = 343.45

Monoclinic,

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 ▶) T min = 0.951, T max = 0.975

36305 measured reflections

3540 independent reflections

2259 reflections with I > 2σ(I)

R int = 0.166

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 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

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

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812048477/is5222sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048477/is5222Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048477/is5222Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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 refinement model (ΔF) (XABS2; Parkin et al., 1995)	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

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)

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) ; (iii) ; (iv) .