Crystal structure of 4-chloro-N-{[1-(4-chloro-benzo-yl)piperidin-4-yl]meth-yl}benzamide monohydrate.

In the title compound, C20H20Cl2N2O2·H2O, the piperidine ring adopts a chair conformation with the two substituent benzene rings inclined to one another [dihedral angle 84.63 (9)°]. In the crystal, the components are linked by Ow-H⋯O, N-H⋯Ow (w = water) and C-H⋯O hydrogen bonds, generating a sheet structure lying parallel to (101).

Related literature

For the synthesis of the title compound, see: Prathebha et al. (2013 ▶). For the biological activity of piperdine derivatives, see: Parthiban et al. (2005 ▶, 2009 ▶, 2011 ▶). For related structures, see: Prathebha et al. (2013 ▶, 2014 ▶); Ávila et al. (2010 ▶).

Experimental

Crystal data

C20H20Cl2N2O2·H2O

M = 409.30

Monoclinic,

a = 8.965 (5) Å

b = 19.613 (5) Å

c = 11.456 (5) Å

β = 96.989 (5)°

V = 1999.3 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 293 K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker APEII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.939, T max = 0.966

18886 measured reflections

4985 independent reflections

2967 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.120

S = 1.03

4985 reflections

252 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814018522/zs2310sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814018522/zs2310Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814018522/zs2310Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814018522/zs2310fig1.tif

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

Click here for additional data file.

a . DOI: 10.1107/S1600536814018522/zs2310fig2.tif

The packing of the mol­ecules in the unit cell, viewed along a. Dashed lines indicate the hydrogen bonds.

Click here for additional data file.

. DOI: 10.1107/S1600536814018522/zs2310fig3.tif

Experimental procedure

CCDC reference: 1014811

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

C20H20Cl2N2O2·H2O	Z = 4
Mr = 409.30	F(000) = 856
Monoclinic, P21/n	Dx = 1.360 Mg m−3
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.965 (5) Å	Cell parameters from 4985 reflections
b = 19.613 (5) Å	µ = 0.35 mm−1
c = 11.456 (5) Å	T = 293 K
β = 96.989 (5)°	Block, colourless
V = 1999.3 (15) Å3	0.20 × 0.15 × 0.10 mm

Bruker APEII CCD diffractometer	4985 independent reflections
Radiation source: fine-focus sealed tube	2967 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω and φ scan	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
Tmin = 0.939, Tmax = 0.966	k = −26→26
18886 measured reflections	l = −15→15

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0472P)2 + 0.401P] where P = (Fo2 + 2Fc2)/3
4985 reflections	(Δ/σ)max < 0.001
252 parameters	Δρmax = 0.23 e Å−3
2 restraints	Δρmin = −0.30 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	0.2856 (2)	0.04517 (10)	−0.36865 (17)	0.0557 (5)
C2	0.1651 (2)	0.05009 (11)	−0.30553 (18)	0.0604 (5)
H2	0.0676	0.0448	−0.3426	0.072*
C3	0.1908 (2)	0.06295 (10)	−0.18659 (17)	0.0548 (5)
H3	0.1096	0.0658	−0.1434	0.066*
C4	0.33501 (19)	0.07168 (9)	−0.13004 (15)	0.0445 (4)
C5	0.4537 (2)	0.06734 (10)	−0.19643 (16)	0.0508 (5)
H5	0.5513	0.0734	−0.1601	0.061*
C6	0.4299 (2)	0.05428 (11)	−0.31542 (17)	0.0550 (5)
H6	0.5105	0.0517	−0.3591	0.066*
C7	0.3542 (2)	0.08172 (10)	0.00066 (16)	0.0499 (5)
C8	0.5234 (2)	0.10784 (10)	0.17983 (15)	0.0525 (5)
H8A	0.6209	0.0872	0.2027	0.063*
H8B	0.4497	0.0820	0.2167	0.063*
C9	0.52633 (19)	0.18034 (10)	0.22638 (14)	0.0443 (4)
H9	0.5999	0.2063	0.1877	0.053*
C10	0.5769 (2)	0.18086 (10)	0.35899 (15)	0.0502 (5)
H10A	0.5085	0.1533	0.3986	0.060*
H10B	0.6764	0.1610	0.3745	0.060*
C11	0.5798 (2)	0.25282 (11)	0.40699 (15)	0.0520 (5)
H11A	0.6068	0.2517	0.4916	0.062*
H11B	0.6553	0.2792	0.3731	0.062*
C12	0.3794 (2)	0.28733 (11)	0.25369 (15)	0.0537 (5)
H12A	0.4454	0.3159	0.2136	0.064*
H12B	0.2794	0.3070	0.2418	0.064*
C13	0.3756 (2)	0.21620 (10)	0.20237 (15)	0.0487 (4)
H13A	0.3469	0.2189	0.1181	0.058*
H13B	0.3000	0.1895	0.2357	0.058*
C14	0.3605 (2)	0.32021 (10)	0.45609 (15)	0.0447 (4)
C15	0.41215 (19)	0.31470 (9)	0.58496 (14)	0.0419 (4)
C16	0.4207 (2)	0.25291 (10)	0.64373 (16)	0.0513 (5)
H16	0.3991	0.2126	0.6023	0.062*
C17	0.4615 (2)	0.25100 (11)	0.76433 (17)	0.0561 (5)
H17	0.4668	0.2096	0.8043	0.067*
C18	0.4939 (2)	0.31065 (11)	0.82394 (15)	0.0533 (5)
C19	0.4847 (2)	0.37221 (11)	0.76756 (16)	0.0558 (5)
H19	0.5066	0.4123	0.8095	0.067*
C20	0.4425 (2)	0.37407 (10)	0.64751 (15)	0.0492 (4)
H20	0.4345	0.4158	0.6086	0.059*
N1	0.48785 (17)	0.10246 (8)	0.05253 (13)	0.0504 (4)
H1	0.5560	0.1131	0.0090	0.061*
N2	0.43298 (16)	0.28557 (8)	0.37952 (12)	0.0483 (4)
O1	0.24827 (16)	0.07042 (10)	0.05634 (13)	0.0782 (5)
O2	0.25144 (15)	0.35694 (7)	0.42328 (11)	0.0607 (4)
O1W	0.1758 (2)	−0.02509 (12)	0.22242 (18)	0.0874 (5)
Cl1	0.25541 (8)	0.02408 (4)	−0.51685 (5)	0.0906 (2)
Cl2	0.54727 (9)	0.30789 (4)	0.97486 (4)	0.0908 (2)
H1WA	0.188 (5)	−0.0575 (19)	0.172 (3)	0.19 (2)*
H1WB	0.181 (9)	0.002 (4)	0.162 (5)	0.34 (4)*

	U11	U22	U33	U12	U13	U23
C1	0.0626 (12)	0.0528 (13)	0.0495 (10)	0.0066 (10)	−0.0011 (9)	−0.0074 (9)
C2	0.0482 (11)	0.0644 (14)	0.0657 (13)	0.0005 (10)	−0.0047 (9)	−0.0062 (10)
C3	0.0457 (10)	0.0572 (13)	0.0622 (12)	−0.0030 (9)	0.0088 (9)	−0.0050 (10)
C4	0.0466 (10)	0.0346 (10)	0.0528 (10)	−0.0020 (8)	0.0076 (8)	−0.0052 (8)
C5	0.0447 (10)	0.0519 (12)	0.0556 (11)	−0.0026 (9)	0.0056 (8)	−0.0118 (9)
C6	0.0534 (11)	0.0591 (13)	0.0539 (11)	0.0027 (9)	0.0119 (9)	−0.0091 (9)
C7	0.0498 (11)	0.0476 (12)	0.0538 (10)	−0.0021 (9)	0.0121 (9)	−0.0048 (9)
C8	0.0574 (11)	0.0545 (13)	0.0458 (10)	0.0015 (9)	0.0073 (8)	−0.0021 (9)
C9	0.0436 (9)	0.0514 (12)	0.0384 (8)	−0.0011 (8)	0.0074 (7)	−0.0037 (8)
C10	0.0437 (10)	0.0646 (14)	0.0420 (9)	0.0108 (9)	0.0035 (7)	−0.0027 (9)
C11	0.0414 (10)	0.0711 (14)	0.0427 (9)	0.0064 (9)	0.0013 (7)	−0.0124 (9)
C12	0.0588 (11)	0.0613 (13)	0.0396 (9)	0.0121 (10)	0.0000 (8)	−0.0028 (9)
C13	0.0477 (10)	0.0586 (12)	0.0386 (8)	0.0028 (9)	0.0001 (7)	−0.0037 (8)
C14	0.0462 (10)	0.0449 (11)	0.0431 (9)	0.0019 (9)	0.0064 (7)	−0.0014 (8)
C15	0.0413 (9)	0.0459 (11)	0.0392 (8)	0.0041 (8)	0.0083 (7)	−0.0010 (8)
C16	0.0591 (11)	0.0428 (11)	0.0520 (10)	0.0007 (9)	0.0068 (8)	−0.0011 (9)
C17	0.0653 (12)	0.0505 (13)	0.0532 (11)	0.0020 (10)	0.0098 (9)	0.0136 (10)
C18	0.0575 (11)	0.0655 (14)	0.0379 (9)	0.0043 (10)	0.0104 (8)	0.0034 (9)
C19	0.0689 (13)	0.0513 (13)	0.0472 (10)	0.0008 (10)	0.0072 (9)	−0.0079 (9)
C20	0.0597 (11)	0.0425 (11)	0.0459 (9)	0.0018 (9)	0.0080 (8)	0.0027 (8)
N1	0.0529 (9)	0.0543 (10)	0.0456 (8)	−0.0062 (8)	0.0124 (7)	−0.0097 (7)
N2	0.0454 (8)	0.0599 (10)	0.0389 (7)	0.0093 (7)	0.0016 (6)	−0.0078 (7)
O1	0.0602 (9)	0.1147 (14)	0.0636 (9)	−0.0184 (9)	0.0238 (7)	−0.0073 (9)
O2	0.0645 (8)	0.0697 (10)	0.0478 (7)	0.0263 (7)	0.0061 (6)	0.0034 (7)
O1W	0.0768 (11)	0.1049 (15)	0.0855 (12)	−0.0057 (10)	0.0296 (9)	−0.0120 (12)
Cl1	0.0863 (4)	0.1263 (6)	0.0551 (3)	0.0222 (4)	−0.0080 (3)	−0.0227 (3)
Cl2	0.1259 (6)	0.1059 (6)	0.0391 (3)	0.0055 (4)	0.0041 (3)	0.0075 (3)

C1—C6	1.373 (3)	C11—H11A	0.9700
C1—C2	1.374 (3)	C11—H11B	0.9700
C1—Cl1	1.736 (2)	C12—N2	1.463 (2)
C2—C3	1.377 (3)	C12—C13	1.513 (3)
C2—H2	0.9300	C12—H12A	0.9700
C3—C4	1.385 (3)	C12—H12B	0.9700
C3—H3	0.9300	C13—H13A	0.9700
C4—C5	1.384 (3)	C13—H13B	0.9700
C4—C7	1.499 (2)	C14—O2	1.235 (2)
C5—C6	1.378 (3)	C14—N2	1.339 (2)
C5—H5	0.9300	C14—C15	1.496 (2)
C6—H6	0.9300	C15—C20	1.377 (3)
C7—O1	1.227 (2)	C15—C16	1.384 (3)
C7—N1	1.334 (2)	C16—C17	1.386 (3)
C8—N1	1.458 (2)	C16—H16	0.9300
C8—C9	1.518 (3)	C17—C18	1.368 (3)
C8—H8A	0.9700	C17—H17	0.9300
C8—H8B	0.9700	C18—C19	1.367 (3)
C9—C13	1.518 (3)	C18—Cl2	1.738 (2)
C9—C10	1.532 (2)	C19—C20	1.382 (2)
C9—H9	0.9800	C19—H19	0.9300
C10—C11	1.514 (3)	C20—H20	0.9300
C10—H10A	0.9700	N1—H1	0.8600
C10—H10B	0.9700	O1W—H1WA	0.872 (19)
C11—N2	1.464 (2)	O1W—H1WB	0.87 (2)
C6—C1—C2	121.02 (19)	C10—C11—H11B	109.5
C6—C1—Cl1	119.43 (16)	H11A—C11—H11B	108.1
C2—C1—Cl1	119.50 (16)	N2—C12—C13	110.51 (15)
C1—C2—C3	119.08 (18)	N2—C12—H12A	109.5
C1—C2—H2	120.5	C13—C12—H12A	109.5
C3—C2—H2	120.5	N2—C12—H12B	109.5
C2—C3—C4	121.31 (18)	C13—C12—H12B	109.5
C2—C3—H3	119.3	H12A—C12—H12B	108.1
C4—C3—H3	119.3	C12—C13—C9	112.27 (15)
C5—C4—C3	118.16 (17)	C12—C13—H13A	109.1
C5—C4—C7	123.68 (16)	C9—C13—H13A	109.1
C3—C4—C7	118.08 (16)	C12—C13—H13B	109.1
C6—C5—C4	121.20 (17)	C9—C13—H13B	109.1
C6—C5—H5	119.4	H13A—C13—H13B	107.9
C4—C5—H5	119.4	O2—C14—N2	121.73 (16)
C1—C6—C5	119.21 (18)	O2—C14—C15	118.73 (15)
C1—C6—H6	120.4	N2—C14—C15	119.53 (15)
C5—C6—H6	120.4	C20—C15—C16	119.44 (16)
O1—C7—N1	122.23 (18)	C20—C15—C14	118.05 (16)
O1—C7—C4	119.57 (17)	C16—C15—C14	122.37 (16)
N1—C7—C4	118.20 (16)	C15—C16—C17	120.06 (18)
N1—C8—C9	114.30 (15)	C15—C16—H16	120.0
N1—C8—H8A	108.7	C17—C16—H16	120.0
C9—C8—H8A	108.7	C18—C17—C16	119.27 (19)
N1—C8—H8B	108.7	C18—C17—H17	120.4
C9—C8—H8B	108.7	C16—C17—H17	120.4
H8A—C8—H8B	107.6	C17—C18—C19	121.51 (17)
C8—C9—C13	113.17 (15)	C17—C18—Cl2	119.09 (16)
C8—C9—C10	110.19 (15)	C19—C18—Cl2	119.40 (16)
C13—C9—C10	109.02 (14)	C18—C19—C20	119.14 (19)
C8—C9—H9	108.1	C18—C19—H19	120.4
C13—C9—H9	108.1	C20—C19—H19	120.4
C10—C9—H9	108.1	C15—C20—C19	120.57 (18)
C11—C10—C9	110.88 (16)	C15—C20—H20	119.7
C11—C10—H10A	109.5	C19—C20—H20	119.7
C9—C10—H10A	109.5	C7—N1—C8	122.88 (15)
C11—C10—H10B	109.5	C7—N1—H1	118.6
C9—C10—H10B	109.5	C8—N1—H1	118.6
H10A—C10—H10B	108.1	C14—N2—C11	125.27 (14)
N2—C11—C10	110.84 (15)	C14—N2—C12	120.41 (15)
N2—C11—H11A	109.5	C11—N2—C12	113.62 (14)
C10—C11—H11A	109.5	H1WA—O1W—H1WB	84 (5)
N2—C11—H11B	109.5
C6—C1—C2—C3	−1.4 (3)	O2—C14—C15—C16	122.3 (2)
Cl1—C1—C2—C3	176.28 (17)	N2—C14—C15—C16	−57.7 (2)
C1—C2—C3—C4	0.7 (3)	C20—C15—C16—C17	−0.8 (3)
C2—C3—C4—C5	0.2 (3)	C14—C15—C16—C17	−176.49 (16)
C2—C3—C4—C7	−176.73 (19)	C15—C16—C17—C18	−0.4 (3)
C3—C4—C5—C6	−0.4 (3)	C16—C17—C18—C19	1.0 (3)
C7—C4—C5—C6	176.32 (18)	C16—C17—C18—Cl2	−179.19 (14)
C2—C1—C6—C5	1.2 (3)	C17—C18—C19—C20	−0.3 (3)
Cl1—C1—C6—C5	−176.49 (16)	Cl2—C18—C19—C20	179.87 (14)
C4—C5—C6—C1	−0.3 (3)	C16—C15—C20—C19	1.5 (3)
C5—C4—C7—O1	−164.2 (2)	C14—C15—C20—C19	177.37 (16)
C3—C4—C7—O1	12.5 (3)	C18—C19—C20—C15	−1.0 (3)
C5—C4—C7—N1	15.3 (3)	O1—C7—N1—C8	5.4 (3)
C3—C4—C7—N1	−167.93 (18)	C4—C7—N1—C8	−174.18 (16)
N1—C8—C9—C13	62.2 (2)	C9—C8—N1—C7	−104.7 (2)
N1—C8—C9—C10	−175.49 (14)	O2—C14—N2—C11	166.40 (19)
C8—C9—C10—C11	−179.77 (15)	C15—C14—N2—C11	−13.5 (3)
C13—C9—C10—C11	−55.0 (2)	O2—C14—N2—C12	−3.4 (3)
C9—C10—C11—N2	56.1 (2)	C15—C14—N2—C12	176.71 (17)
N2—C12—C13—C9	−54.7 (2)	C10—C11—N2—C14	132.70 (18)
C8—C9—C13—C12	177.72 (15)	C10—C11—N2—C12	−56.9 (2)
C10—C9—C13—C12	54.7 (2)	C13—C12—N2—C14	−133.45 (18)
O2—C14—C15—C20	−53.4 (2)	C13—C12—N2—C11	55.7 (2)
N2—C14—C15—C20	126.55 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.19	3.043 (2)	171
O1W—H1WA···O2ii	0.87 (2)	2.11 (2)	2.972 (3)	169 (4)
O1W—H1WB···O1	0.87 (2)	1.96 (3)	2.802 (3)	163 (7)
C5—H5···O2i	0.93	2.36	3.212 (3)	152
C8—H8B···O1	0.97	2.43	2.789 (3)	102
C12—H12B···O2	0.97	2.34	2.738 (2)	104

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.19	3.043 (2)	171
O1W—H1WA⋯O2ii	0.87 (2)	2.11 (2)	2.972 (3)	169 (4)
O1W—H1WB⋯O1	0.87 (2)	1.96 (3)	2.802 (3)	163 (7)
C5—H5⋯O2i	0.93	2.36	3.212 (3)	152

Symmetry codes: (i) ; (ii) .