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

In the title compound, C15H22N2O·H2O, the dihedral angle between the planes of the piperidine and benzene rings is 31.63 (1)°. The piperidine ring adopts a chair conformation. The water solvent mol-ecule is involved in inter-species O-H⋯O, O-H⋯N, N-H⋯O and weak C-H⋯O hydrogen-bonding inter-actions, giving rise to chains extending along [010].

Related literature

For the biological activity of piperidine and benzamide derivatives, see: Ramalingan et al. (2004 ▸); Sargent & May (1970 ▸); Magar et al. (2010 ▸); Fun et al. (2011 ▸); Haffner et al. (2010 ▸); Lavanya et al. (2010 ▸). For related structures, see: Ávila et al. (2010 ▸); Prathebha et al. (2014 ▸, 2015 ▸); Al-abbasi et al. (2010 ▸). For the synthesis, see: Prathebha et al. (2014 ▸, 2015 ▸).

Experimental

Crystal data

C15H22N2O·H2O

M = 264.36

Monoclinic,

a = 14.8504 (17) Å

b = 6.8243 (6) Å

c = 15.0070 (18) Å

β = 98.653 (4)°

V = 1503.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.24 × 0.22 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T min = 0.980, T max = 0.986

25938 measured reflections

3735 independent reflections

2311 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.203

S = 1.11

3688 reflections

181 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: APEX2 and SAINT (Bruker, 2004 ▸); data reduction: SAINT and XPREP (Bruker, 2004 ▸); 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.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015007653/zs2330sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015007653/zs2330Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015007653/zs2330Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015007653/zs2330fig1.tif

The mol­ecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015007653/zs2330fig2.tif

The packing of the mol­ecules in the crystal structure. The dashed lines indicate hydrogen bonds.

CCDC reference: 1054604

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

C15H22N2O·H2O	F(000) = 576
Mr = 264.36	Dx = 1.168 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.8504 (17) Å	θ = 1.4–28.3°
b = 6.8243 (6) Å	µ = 0.08 mm−1
c = 15.0070 (18) Å	T = 293 K
β = 98.653 (4)°	Block, colourless
V = 1503.6 (3) Å3	0.24 × 0.22 × 0.22 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3735 independent reflections
Radiation source: fine-focus sealed tube	2311 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scans	θmax = 28.3°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −19→19
Tmin = 0.980, Tmax = 0.986	k = −9→9
25938 measured reflections	l = −19→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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.203	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.0894P)2 + 0.5035P] where P = (Fo2 + 2Fc2)/3
3688 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.34 e Å−3
3 restraints	Δρmin = −0.22 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
C1	0.38752 (16)	0.4342 (3)	0.07521 (17)	0.0542 (6)
H1A	0.3939	0.4274	0.0119	0.065*
H1B	0.4338	0.5227	0.1046	0.065*
C2	0.29416 (17)	0.5141 (4)	0.08428 (19)	0.0636 (7)
H2A	0.2896	0.5320	0.1476	0.076*
H2B	0.2861	0.6408	0.0549	0.076*
C3	0.22041 (17)	0.3770 (4)	0.04252 (19)	0.0665 (7)
H3A	0.1619	0.4229	0.0553	0.080*
H3B	0.2186	0.3751	−0.0224	0.080*
C4	0.23786 (17)	0.1739 (4)	0.0794 (2)	0.0657 (7)
H4A	0.2303	0.1724	0.1425	0.079*
H4B	0.1936	0.0845	0.0473	0.079*
C5	0.33188 (17)	0.1055 (4)	0.0704 (2)	0.0635 (7)
H5A	0.3415	−0.0241	0.0966	0.076*
H5B	0.3377	0.0961	0.0070	0.076*
C6	0.49185 (15)	0.1599 (4)	0.10743 (17)	0.0541 (6)
H6A	0.5052	0.1855	0.0472	0.065*
H6B	0.4909	0.0190	0.1156	0.065*
C7	0.56594 (14)	0.2458 (4)	0.17469 (18)	0.0558 (6)
H7A	0.5700	0.3857	0.1646	0.067*
H7B	0.5519	0.2259	0.2351	0.067*
C8	0.72909 (13)	0.2522 (3)	0.16379 (13)	0.0409 (5)
C9	0.81183 (13)	0.1325 (3)	0.15644 (13)	0.0386 (4)
C10	0.82043 (14)	−0.0617 (3)	0.18282 (15)	0.0471 (5)
H10	0.7727	−0.1231	0.2054	0.057*
C11	0.89864 (15)	−0.1651 (3)	0.17615 (16)	0.0517 (6)
H11	0.9028	−0.2954	0.1945	0.062*
C12	0.97060 (14)	−0.0808 (4)	0.14315 (14)	0.0500 (5)
C13	0.96249 (15)	0.1133 (4)	0.11755 (16)	0.0553 (6)
H13	1.0104	0.1739	0.0949	0.066*
C14	0.88495 (15)	0.2194 (3)	0.12477 (15)	0.0500 (5)
H14	0.8818	0.3509	0.1082	0.060*
C15	1.05545 (18)	−0.1956 (5)	0.1353 (2)	0.0762 (8)
H15A	1.0492	−0.3265	0.1571	0.114*
H15B	1.1069	−0.1334	0.1706	0.114*
H15C	1.0645	−0.2002	0.0734	0.114*
N1	0.40171 (11)	0.2394 (2)	0.11529 (12)	0.0452 (4)
N2	0.65238 (11)	0.1538 (3)	0.16645 (13)	0.0497 (5)
H2	0.6540	0.0281	0.1631	0.060*
O1	0.73327 (11)	0.4323 (2)	0.16610 (13)	0.0613 (5)
O1W	0.61401 (11)	−0.2569 (2)	0.19557 (13)	0.0553 (5)
H1W	0.6502 (18)	−0.350 (4)	0.189 (2)	0.090 (10)*
H2W	0.611 (2)	−0.259 (5)	0.2514 (13)	0.116 (14)*

	U11	U22	U33	U12	U13	U23
C1	0.0519 (13)	0.0525 (13)	0.0580 (13)	−0.0099 (10)	0.0078 (10)	0.0021 (10)
C2	0.0657 (16)	0.0500 (13)	0.0732 (16)	0.0106 (12)	0.0042 (12)	0.0045 (12)
C3	0.0461 (14)	0.0774 (17)	0.0734 (17)	0.0080 (12)	0.0002 (11)	−0.0027 (14)
C4	0.0479 (14)	0.0703 (16)	0.0779 (17)	−0.0168 (12)	0.0061 (12)	−0.0064 (14)
C5	0.0588 (15)	0.0482 (13)	0.0813 (18)	−0.0057 (11)	0.0028 (12)	−0.0127 (12)
C6	0.0449 (12)	0.0551 (13)	0.0632 (14)	0.0039 (10)	0.0108 (10)	−0.0128 (11)
C7	0.0366 (11)	0.0558 (13)	0.0760 (16)	0.0008 (10)	0.0114 (10)	−0.0201 (12)
C8	0.0398 (11)	0.0414 (10)	0.0423 (10)	0.0025 (8)	0.0088 (8)	0.0009 (8)
C9	0.0353 (10)	0.0412 (10)	0.0400 (10)	−0.0013 (8)	0.0078 (8)	−0.0015 (8)
C10	0.0385 (11)	0.0454 (11)	0.0584 (13)	−0.0032 (9)	0.0107 (9)	0.0045 (9)
C11	0.0467 (12)	0.0446 (12)	0.0631 (14)	0.0061 (10)	0.0059 (10)	0.0037 (10)
C12	0.0396 (11)	0.0662 (14)	0.0441 (11)	0.0117 (10)	0.0060 (9)	0.0054 (10)
C13	0.0383 (11)	0.0726 (15)	0.0579 (13)	0.0011 (10)	0.0164 (9)	0.0152 (11)
C14	0.0462 (12)	0.0475 (11)	0.0581 (13)	−0.0004 (10)	0.0140 (10)	0.0111 (10)
C15	0.0564 (16)	0.103 (2)	0.0723 (17)	0.0339 (15)	0.0197 (13)	0.0177 (16)
N1	0.0375 (9)	0.0439 (9)	0.0546 (10)	0.0010 (7)	0.0085 (7)	−0.0041 (8)
N2	0.0355 (9)	0.0418 (9)	0.0729 (12)	0.0023 (7)	0.0118 (8)	−0.0075 (9)
O1	0.0545 (10)	0.0403 (8)	0.0941 (13)	0.0015 (7)	0.0270 (9)	−0.0002 (8)
O1W	0.0542 (10)	0.0416 (9)	0.0731 (13)	0.0003 (7)	0.0194 (8)	−0.0004 (8)

C1—N1	1.461 (3)	C7—H7B	0.9700
C1—C2	1.515 (3)	C8—O1	1.231 (2)
C1—H1A	0.9700	C8—N2	1.328 (3)
C1—H1B	0.9700	C8—C9	1.493 (3)
C2—C3	1.504 (4)	C9—C14	1.383 (3)
C2—H2A	0.9700	C9—C10	1.383 (3)
C2—H2B	0.9700	C10—C11	1.376 (3)
C3—C4	1.501 (4)	C10—H10	0.9300
C3—H3A	0.9700	C11—C12	1.370 (3)
C3—H3B	0.9700	C11—H11	0.9300
C4—C5	1.498 (3)	C12—C13	1.379 (3)
C4—H4A	0.9700	C12—C15	1.503 (3)
C4—H4B	0.9700	C13—C14	1.378 (3)
C5—N1	1.468 (3)	C13—H13	0.9300
C5—H5A	0.9700	C14—H14	0.9300
C5—H5B	0.9700	C15—H15A	0.9600
C6—N1	1.465 (3)	C15—H15B	0.9600
C6—C7	1.496 (3)	C15—H15C	0.9600
C6—H6A	0.9700	N2—H2	0.8600
C6—H6B	0.9700	O1W—H1W	0.849 (17)
C7—N2	1.451 (3)	O1W—H2W	0.845 (18)
C7—H7A	0.9700
N1—C1—C2	111.57 (19)	C6—C7—H7A	109.6
N1—C1—H1A	109.3	N2—C7—H7B	109.6
C2—C1—H1A	109.3	C6—C7—H7B	109.6
N1—C1—H1B	109.3	H7A—C7—H7B	108.2
C2—C1—H1B	109.3	O1—C8—N2	122.92 (18)
H1A—C1—H1B	108.0	O1—C8—C9	120.65 (18)
C3—C2—C1	111.0 (2)	N2—C8—C9	116.43 (17)
C3—C2—H2A	109.4	C14—C9—C10	117.78 (18)
C1—C2—H2A	109.4	C14—C9—C8	119.21 (18)
C3—C2—H2B	109.4	C10—C9—C8	122.98 (17)
C1—C2—H2B	109.4	C11—C10—C9	120.89 (19)
H2A—C2—H2B	108.0	C11—C10—H10	119.6
C4—C3—C2	110.3 (2)	C9—C10—H10	119.6
C4—C3—H3A	109.6	C12—C11—C10	121.6 (2)
C2—C3—H3A	109.6	C12—C11—H11	119.2
C4—C3—H3B	109.6	C10—C11—H11	119.2
C2—C3—H3B	109.6	C11—C12—C13	117.63 (19)
H3A—C3—H3B	108.1	C11—C12—C15	121.2 (2)
C5—C4—C3	111.5 (2)	C13—C12—C15	121.2 (2)
C5—C4—H4A	109.3	C14—C13—C12	121.4 (2)
C3—C4—H4A	109.3	C14—C13—H13	119.3
C5—C4—H4B	109.3	C12—C13—H13	119.3
C3—C4—H4B	109.3	C13—C14—C9	120.7 (2)
H4A—C4—H4B	108.0	C13—C14—H14	119.7
N1—C5—C4	111.6 (2)	C9—C14—H14	119.7
N1—C5—H5A	109.3	C12—C15—H15A	109.5
C4—C5—H5A	109.3	C12—C15—H15B	109.5
N1—C5—H5B	109.3	H15A—C15—H15B	109.5
C4—C5—H5B	109.3	C12—C15—H15C	109.5
H5A—C5—H5B	108.0	H15A—C15—H15C	109.5
N1—C6—C7	112.87 (18)	H15B—C15—H15C	109.5
N1—C6—H6A	109.0	C1—N1—C6	112.36 (18)
C7—C6—H6A	109.0	C1—N1—C5	109.23 (18)
N1—C6—H6B	109.0	C6—N1—C5	108.86 (17)
C7—C6—H6B	109.0	C8—N2—C7	123.92 (18)
H6A—C6—H6B	107.8	C8—N2—H2	118.0
N2—C7—C6	110.08 (18)	C7—N2—H2	118.0
N2—C7—H7A	109.6	H1W—O1W—H2W	103 (2)
N1—C1—C2—C3	−56.8 (3)	C11—C12—C13—C14	0.0 (3)
C1—C2—C3—C4	52.5 (3)	C15—C12—C13—C14	−179.8 (2)
C2—C3—C4—C5	−53.0 (3)	C12—C13—C14—C9	−1.3 (4)
C3—C4—C5—N1	57.1 (3)	C10—C9—C14—C13	1.8 (3)
N1—C6—C7—N2	177.01 (19)	C8—C9—C14—C13	179.7 (2)
O1—C8—C9—C14	−19.8 (3)	C2—C1—N1—C6	−179.81 (19)
N2—C8—C9—C14	159.4 (2)	C2—C1—N1—C5	59.3 (3)
O1—C8—C9—C10	157.9 (2)	C7—C6—N1—C1	77.8 (3)
N2—C8—C9—C10	−22.9 (3)	C7—C6—N1—C5	−161.1 (2)
C14—C9—C10—C11	−1.1 (3)	C4—C5—N1—C1	−59.5 (3)
C8—C9—C10—C11	−178.91 (19)	C4—C5—N1—C6	177.5 (2)
C9—C10—C11—C12	−0.1 (3)	O1—C8—N2—C7	−1.7 (3)
C10—C11—C12—C13	0.7 (3)	C9—C8—N2—C7	179.16 (19)
C10—C11—C12—C15	−179.4 (2)	C6—C7—N2—C8	133.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O1i	0.85 (2)	1.99 (2)	2.840 (2)	177 (3)
O1W—H2W···N1ii	0.85 (2)	2.04 (2)	2.883 (3)	177 (3)
N2—H2···O1W	0.86	2.11	2.906 (2)	153
C7—H7A···O1Wiii	0.97	2.55	3.472 (3)	159
C7—H7A···O1	0.97	2.44	2.812 (3)	102
C10—H10···O1W	0.93	2.51	3.374 (3)	154

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1WH1WO1i	0.85(2)	1.99(2)	2.840(2)	177(3)
O1WH2WN1ii	0.85(2)	2.04(2)	2.883(3)	177(3)
N2H2O1W	0.86	2.11	2.906(2)	153
C7H7AO1W iii	0.97	2.55	3.472(3)	159
C10H10O1W	0.93	2.51	3.374(3)	154

Symmetry codes: (i) ; (ii) ; (iii) .