Crystal structure of 4-chloro-N-[2-(piperidin-1-yl)eth-yl]benzamide monohydrate.

In the title compound, C14H19ClN2O2·H2O, the piperdine ring adopts a chair conformation. The dihedral angle between the mean plane of the piperidine ring and that of the phenyl ring is 41.64 (1)°. In the crystal, mol-ecules are linked by O-H⋯N, N-H⋯O and C-H⋯O hydrogen bonds involving the water mol-ecule, forming double-stranded chains propagating along [010].

Related literature

For the synthesis of the title compound, see: Prathebha et al. (2013 ▸, 2014 ▸). For the biological activities of piperdine derivatives, see: Pandey & Chawla (2012 ▸); Jayalakshmi & Nanjundan (2008 ▸); Parthiban et al. (2005 ▸); Aridoss et al. (2008 ▸); Ramachandran et al. (2011 ▸). For related structures, see: Prathebha et al. (2014 ▸); Ávila et al. (2010 ▸); Al-abbasi et al. (2010 ▸).

Experimental

Crystal data

C14H19ClN2O·H2O

M = 284.78

Monoclinic,

a = 14.9115 (6) Å

b = 6.6899 (3) Å

c = 15.6215 (7) Å

β = 102.956 (2)°

V = 1518.67 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.25 × 0.23 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T min = 0.939, T max = 0.951

12566 measured reflections

3780 independent reflections

1953 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.160

S = 1.01

3780 reflections

181 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); data reduction: XPREP in SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989014026851/su5034sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014026851/su5034Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989014026851/su5034Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989014026851/su5034fig1.tif

The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

b . DOI: 10.1107/S2056989014026851/su5034fig2.tif

A view along the b axis of the crystal packing of the title compound. The dashed lines indicate the hydrogen bonds (see Table 1 for details; C-bound H atoms have been omitted for clarity).

CCDC reference: 1038084

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H19ClN2O·H2O	F(000) = 608
Mr = 284.78	Dx = 1.245 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3780 reflections
a = 14.9115 (6) Å	θ = 1.7–28.4°
b = 6.6899 (3) Å	µ = 0.25 mm−1
c = 15.6215 (7) Å	T = 293 K
β = 102.956 (2)°	Block, colourless
V = 1518.67 (11) Å3	0.25 × 0.23 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3780 independent reflections
Radiation source: fine-focus sealed tube	1953 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω and φ scan	θmax = 28.4°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −19→19
Tmin = 0.939, Tmax = 0.951	k = −8→7
12566 measured reflections	l = −20→20

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0714P)2 + 0.2535P] where P = (Fo2 + 2Fc2)/3
3780 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.28 e Å−3
2 restraints	Δρmin = −0.21 e Å−3

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
O1W	0.36430 (12)	−0.0064 (2)	0.33083 (13)	0.0544 (4)
H1WA	0.3601 (17)	−0.005 (4)	0.2772 (11)	0.062 (8)*
H1WB	0.3987 (15)	0.082 (3)	0.3533 (15)	0.064 (8)*
C1	0.13069 (15)	−0.6539 (4)	0.39904 (16)	0.0561 (6)
H1A	0.1347	−0.6240	0.4605	0.067*
H1B	0.1773	−0.7528	0.3957	0.067*
C2	0.03637 (15)	−0.7388 (4)	0.35887 (18)	0.0671 (7)
H2A	0.0342	−0.7795	0.2988	0.081*
H2B	0.0257	−0.8563	0.3916	0.081*
C3	−0.03859 (16)	−0.5866 (4)	0.35964 (18)	0.0682 (7)
H3A	−0.0428	−0.5605	0.4197	0.082*
H3B	−0.0973	−0.6390	0.3279	0.082*
C4	−0.01743 (15)	−0.3941 (4)	0.31710 (18)	0.0665 (7)
H4A	−0.0223	−0.4163	0.2549	0.080*
H4B	−0.0621	−0.2930	0.3234	0.080*
C5	0.07842 (15)	−0.3203 (4)	0.35883 (17)	0.0610 (7)
H5A	0.0910	−0.1994	0.3293	0.073*
H5B	0.0817	−0.2878	0.4200	0.073*
C6	0.24037 (14)	−0.3914 (3)	0.38842 (15)	0.0508 (6)
H6A	0.2500	−0.3780	0.4517	0.061*
H6B	0.2448	−0.2593	0.3641	0.061*
C7	0.31449 (13)	−0.5225 (3)	0.36732 (16)	0.0511 (6)
H7A	0.3226	−0.6393	0.4051	0.061*
H7B	0.2961	−0.5678	0.3069	0.061*
C8	0.48147 (13)	−0.5074 (3)	0.38619 (13)	0.0411 (5)
C9	0.56372 (13)	−0.3766 (3)	0.39205 (13)	0.0405 (5)
C10	0.63653 (15)	−0.4479 (4)	0.35953 (15)	0.0530 (6)
H10	0.6343	−0.5769	0.3370	0.064*
C11	0.71251 (15)	−0.3293 (4)	0.36017 (16)	0.0633 (7)
H11	0.7610	−0.3773	0.3377	0.076*
C12	0.71562 (14)	−0.1406 (4)	0.39423 (16)	0.0552 (6)
C13	0.64543 (15)	−0.0669 (4)	0.42879 (15)	0.0541 (6)
H13	0.6491	0.0607	0.4529	0.065*
C14	0.56919 (14)	−0.1860 (3)	0.42700 (14)	0.0479 (5)
H14	0.5209	−0.1371	0.4497	0.058*
N1	0.14836 (11)	−0.4716 (2)	0.35340 (11)	0.0435 (4)
N2	0.40087 (11)	−0.4147 (3)	0.37969 (11)	0.0480 (5)
H2	0.4002	−0.2864	0.3830	0.058*
O1	0.48880 (10)	−0.6908 (2)	0.38625 (10)	0.0573 (4)
Cl1	0.81091 (5)	0.01012 (12)	0.39483 (6)	0.0952 (3)

	U11	U22	U33	U12	U13	U23
O1W	0.0567 (10)	0.0380 (10)	0.0677 (12)	−0.0102 (8)	0.0123 (9)	0.0000 (9)
C1	0.0484 (13)	0.0450 (14)	0.0746 (15)	−0.0061 (11)	0.0129 (11)	0.0122 (12)
C2	0.0503 (14)	0.0549 (16)	0.0971 (19)	−0.0147 (12)	0.0184 (13)	0.0019 (14)
C3	0.0445 (13)	0.0754 (19)	0.0887 (18)	−0.0116 (13)	0.0234 (12)	−0.0014 (15)
C4	0.0427 (13)	0.0672 (18)	0.0939 (18)	0.0093 (12)	0.0244 (12)	0.0050 (15)
C5	0.0478 (13)	0.0479 (15)	0.0937 (18)	0.0037 (11)	0.0297 (12)	−0.0020 (13)
C6	0.0437 (12)	0.0424 (13)	0.0682 (14)	−0.0064 (10)	0.0164 (10)	−0.0050 (11)
C7	0.0364 (11)	0.0373 (13)	0.0779 (15)	−0.0021 (9)	0.0091 (10)	−0.0042 (11)
C8	0.0383 (11)	0.0353 (12)	0.0482 (12)	−0.0031 (9)	0.0067 (8)	−0.0020 (9)
C9	0.0365 (10)	0.0375 (12)	0.0456 (11)	−0.0029 (9)	0.0049 (8)	0.0003 (9)
C10	0.0440 (12)	0.0439 (13)	0.0720 (15)	−0.0020 (10)	0.0150 (11)	−0.0097 (11)
C11	0.0442 (13)	0.0648 (18)	0.0857 (18)	−0.0042 (12)	0.0247 (12)	−0.0076 (14)
C12	0.0413 (12)	0.0530 (16)	0.0710 (15)	−0.0140 (10)	0.0121 (11)	0.0048 (12)
C13	0.0495 (13)	0.0394 (13)	0.0718 (15)	−0.0083 (10)	0.0102 (11)	−0.0057 (11)
C14	0.0397 (11)	0.0420 (13)	0.0628 (14)	−0.0029 (9)	0.0129 (10)	−0.0057 (11)
N1	0.0361 (9)	0.0344 (10)	0.0610 (11)	−0.0010 (7)	0.0132 (8)	0.0014 (8)
N2	0.0360 (9)	0.0314 (10)	0.0751 (12)	−0.0035 (7)	0.0094 (8)	−0.0013 (9)
O1	0.0493 (9)	0.0342 (10)	0.0869 (11)	−0.0040 (7)	0.0124 (8)	−0.0050 (8)
Cl1	0.0650 (5)	0.0851 (6)	0.1438 (8)	−0.0346 (4)	0.0410 (5)	−0.0043 (5)

O1W—H1WA	0.826 (16)	C6—H6A	0.9700
O1W—H1WB	0.808 (16)	C6—H6B	0.9700
C1—N1	1.466 (3)	C7—N2	1.451 (2)
C1—C2	1.516 (3)	C7—H7A	0.9700
C1—H1A	0.9700	C7—H7B	0.9700
C1—H1B	0.9700	C8—O1	1.231 (2)
C2—C3	1.514 (3)	C8—N2	1.336 (2)
C2—H2A	0.9700	C8—C9	1.493 (3)
C2—H2B	0.9700	C9—C10	1.383 (3)
C3—C4	1.515 (4)	C9—C14	1.382 (3)
C3—H3A	0.9700	C10—C11	1.381 (3)
C3—H3B	0.9700	C10—H10	0.9300
C4—C5	1.514 (3)	C11—C12	1.366 (3)
C4—H4A	0.9700	C11—H11	0.9300
C4—H4B	0.9700	C12—C13	1.372 (3)
C5—N1	1.469 (3)	C12—Cl1	1.741 (2)
C5—H5A	0.9700	C13—C14	1.383 (3)
C5—H5B	0.9700	C13—H13	0.9300
C6—N1	1.460 (3)	C14—H14	0.9300
C6—C7	1.504 (3)	N2—H2	0.8600
H1WA—O1W—H1WB	109 (2)	C7—C6—H6B	109.2
N1—C1—C2	111.19 (19)	H6A—C6—H6B	107.9
N1—C1—H1A	109.4	N2—C7—C6	110.77 (17)
C2—C1—H1A	109.4	N2—C7—H7A	109.5
N1—C1—H1B	109.4	C6—C7—H7A	109.5
C2—C1—H1B	109.4	N2—C7—H7B	109.5
H1A—C1—H1B	108.0	C6—C7—H7B	109.5
C3—C2—C1	111.3 (2)	H7A—C7—H7B	108.1
C3—C2—H2A	109.4	O1—C8—N2	122.74 (18)
C1—C2—H2A	109.4	O1—C8—C9	120.83 (18)
C3—C2—H2B	109.4	N2—C8—C9	116.42 (18)
C1—C2—H2B	109.4	C10—C9—C14	118.80 (18)
H2A—C2—H2B	108.0	C10—C9—C8	118.50 (18)
C2—C3—C4	109.98 (18)	C14—C9—C8	122.69 (18)
C2—C3—H3A	109.7	C11—C10—C9	120.6 (2)
C4—C3—H3A	109.7	C11—C10—H10	119.7
C2—C3—H3B	109.7	C9—C10—H10	119.7
C4—C3—H3B	109.7	C12—C11—C10	119.3 (2)
H3A—C3—H3B	108.2	C12—C11—H11	120.3
C5—C4—C3	110.9 (2)	C10—C11—H11	120.3
C5—C4—H4A	109.4	C11—C12—C13	121.5 (2)
C3—C4—H4A	109.4	C11—C12—Cl1	119.58 (18)
C5—C4—H4B	109.4	C13—C12—Cl1	118.89 (19)
C3—C4—H4B	109.4	C12—C13—C14	118.7 (2)
H4A—C4—H4B	108.0	C12—C13—H13	120.6
N1—C5—C4	111.4 (2)	C14—C13—H13	120.6
N1—C5—H5A	109.4	C9—C14—C13	120.98 (19)
C4—C5—H5A	109.4	C9—C14—H14	119.5
N1—C5—H5B	109.4	C13—C14—H14	119.5
C4—C5—H5B	109.4	C6—N1—C1	112.30 (17)
H5A—C5—H5B	108.0	C6—N1—C5	110.17 (17)
N1—C6—C7	112.24 (17)	C1—N1—C5	109.74 (16)
N1—C6—H6A	109.2	C8—N2—C7	122.38 (17)
C7—C6—H6A	109.2	C8—N2—H2	118.8
N1—C6—H6B	109.2	C7—N2—H2	118.8
N1—C1—C2—C3	−57.0 (3)	C11—C12—C13—C14	−1.4 (4)
C1—C2—C3—C4	53.1 (3)	Cl1—C12—C13—C14	179.04 (17)
C2—C3—C4—C5	−53.1 (3)	C10—C9—C14—C13	0.7 (3)
C3—C4—C5—N1	57.3 (3)	C8—C9—C14—C13	−178.0 (2)
N1—C6—C7—N2	163.46 (18)	C12—C13—C14—C9	0.7 (3)
O1—C8—C9—C10	28.2 (3)	C7—C6—N1—C1	69.4 (2)
N2—C8—C9—C10	−150.8 (2)	C7—C6—N1—C5	−167.94 (19)
O1—C8—C9—C14	−153.1 (2)	C2—C1—N1—C6	−177.55 (19)
N2—C8—C9—C14	27.9 (3)	C2—C1—N1—C5	59.6 (2)
C14—C9—C10—C11	−1.4 (3)	C4—C5—N1—C6	175.98 (19)
C8—C9—C10—C11	177.3 (2)	C4—C5—N1—C1	−59.9 (2)
C9—C10—C11—C12	0.7 (4)	O1—C8—N2—C7	−3.5 (3)
C10—C11—C12—C13	0.8 (4)	C9—C8—N2—C7	175.58 (18)
C10—C11—C12—Cl1	−179.72 (18)	C6—C7—N2—C8	163.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···N1i	0.83 (2)	2.03 (2)	2.851 (3)	174 (2)
N2—H2···O1W	0.86	2.06	2.855 (2)	153
C6—H6B···O1W	0.97	2.59	3.406 (3)	142

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1WH1WAN1i	0.83(2)	2.03(2)	2.851(3)	174(2)
N2H2O1W	0.86	2.06	2.855(2)	153
C6H6BO1W	0.97	2.59	3.406(3)	142

Symmetry code: (i) .