3-[(E)-2,4-Dichloro-benzyl-idene]-1-methyl-piperidin-4-one.

The piperidine ring of the title compound, C(13)H(13)Cl(2)NO, adopts an envelope conformation. Inter-molecular C-H⋯O inter-actions link the mol-ecules into a C(7) chain running along the b axis.

Related literature

For biological activities of 4-piperidones, see: Badorrey et al. (1999 ▶); Grishina et al. (1994 ▶); Nalanishi et al. (1974a ▶,b ▶). For ring conformations, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C13H13Cl2NO

M = 270.14

Monoclinic,

a = 12.2013 (9) Å

b = 8.5901 (6) Å

c = 12.6391 (9) Å

β = 92.997 (1)°

V = 1322.90 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.47 mm−1

T = 293 (2) K

0.24 × 0.23 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: none

14377 measured reflections

3071 independent reflections

2654 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.120

S = 0.97

3071 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808002286/ci2557sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002286/ci2557Isup2.hkl

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

C13H13Cl2NO	F000 = 560
Mr = 270.14	Dx = 1.356 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1509 reflections
a = 12.2013 (9) Å	θ = 2.3–25.0º
b = 8.5901 (6) Å	µ = 0.47 mm−1
c = 12.6391 (9) Å	T = 293 (2) K
β = 92.997 (1)º	Block, pale yellow
V = 1322.90 (16) Å3	0.24 × 0.23 × 0.20 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2654 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Monochromator: graphite	θmax = 28.1º
T = 293(2) K	θmin = 2.3º
ω scans	h = −15→15
Absorption correction: none	k = −10→11
14377 measured reflections	l = −16→16
3071 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0724P)2 + 0.3356P] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max = 0.001
3071 reflections	Δρmax = 0.34 e Å−3
155 parameters	Δρmin = −0.27 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.53390 (18)	0.5088 (2)	1.24853 (18)	0.0781 (5)
H1A	0.5518	0.5079	1.1755	0.117*
H1B	0.5966	0.5421	1.2917	0.117*
H1C	0.4740	0.5792	1.2576	0.117*
C2	0.47091 (17)	0.3512 (2)	1.38999 (14)	0.0700 (5)
H2A	0.4038	0.4104	1.3959	0.084*
H2B	0.5280	0.4004	1.4346	0.084*
C3	0.4536 (2)	0.1860 (3)	1.42729 (13)	0.0791 (6)
H3A	0.5248	0.1374	1.4403	0.095*
H3B	0.4182	0.1896	1.4942	0.095*
C4	0.38604 (15)	0.0855 (2)	1.35183 (13)	0.0660 (5)
C5	0.37681 (12)	0.1336 (2)	1.23733 (11)	0.0524 (3)
C6	0.41053 (13)	0.29745 (19)	1.21048 (12)	0.0532 (3)
H6A	0.4317	0.3008	1.1376	0.064*
H6B	0.3484	0.3667	1.2168	0.064*
C7	0.34326 (12)	0.0240 (2)	1.16663 (12)	0.0545 (4)
H7	0.3257	−0.0728	1.1939	0.065*
C8	0.33134 (11)	0.04126 (18)	1.05058 (11)	0.0486 (3)
C9	0.35991 (12)	−0.08015 (17)	0.98306 (12)	0.0489 (3)
C10	0.35760 (12)	−0.06504 (17)	0.87383 (12)	0.0496 (3)
H10	0.3791	−0.1465	0.8311	0.059*
C11	0.32225 (13)	0.07535 (18)	0.83036 (11)	0.0500 (3)
C12	0.28628 (14)	0.19534 (19)	0.89226 (13)	0.0565 (4)
H12	0.2592	0.2867	0.8613	0.068*
C13	0.29116 (13)	0.17732 (19)	1.00152 (13)	0.0557 (4)
H13	0.2670	0.2581	1.0434	0.067*
N1	0.50222 (11)	0.35202 (16)	1.28025 (10)	0.0539 (3)
O1	0.34393 (15)	−0.0325 (2)	1.38258 (12)	0.1014 (6)
Cl1	0.40318 (5)	−0.25836 (5)	1.03652 (4)	0.07721 (18)
Cl2	0.32208 (5)	0.09909 (5)	0.69335 (3)	0.07158 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0843 (13)	0.0546 (10)	0.0934 (14)	−0.0057 (9)	−0.0158 (11)	0.0027 (10)
C2	0.0752 (11)	0.0799 (12)	0.0544 (9)	0.0079 (9)	−0.0035 (8)	−0.0182 (9)
C3	0.0949 (14)	0.1009 (15)	0.0412 (8)	−0.0155 (12)	0.0012 (8)	0.0010 (9)
C4	0.0617 (9)	0.0896 (13)	0.0472 (8)	−0.0133 (9)	0.0065 (7)	0.0089 (8)
C5	0.0465 (7)	0.0672 (9)	0.0437 (7)	−0.0049 (6)	0.0037 (6)	0.0033 (6)
C6	0.0523 (8)	0.0595 (9)	0.0475 (7)	0.0023 (7)	−0.0001 (6)	−0.0007 (7)
C7	0.0509 (8)	0.0625 (9)	0.0501 (8)	−0.0084 (7)	0.0038 (6)	0.0046 (7)
C8	0.0424 (7)	0.0541 (8)	0.0493 (7)	−0.0043 (6)	0.0011 (5)	−0.0007 (6)
C9	0.0473 (7)	0.0448 (7)	0.0543 (8)	−0.0020 (6)	−0.0011 (6)	0.0045 (6)
C10	0.0512 (7)	0.0460 (7)	0.0513 (8)	−0.0012 (6)	0.0016 (6)	−0.0035 (6)
C11	0.0535 (8)	0.0504 (7)	0.0455 (7)	−0.0036 (6)	−0.0018 (6)	0.0003 (6)
C12	0.0639 (9)	0.0483 (8)	0.0563 (8)	0.0069 (7)	−0.0084 (7)	−0.0006 (7)
C13	0.0561 (8)	0.0555 (8)	0.0549 (8)	0.0071 (7)	−0.0032 (6)	−0.0090 (7)
N1	0.0546 (7)	0.0524 (7)	0.0540 (7)	0.0017 (5)	−0.0029 (5)	−0.0036 (5)
O1	0.1116 (12)	0.1262 (13)	0.0654 (8)	−0.0543 (11)	−0.0048 (8)	0.0325 (9)
Cl1	0.1059 (4)	0.0545 (3)	0.0708 (3)	0.0144 (2)	0.0005 (3)	0.01340 (19)
Cl2	0.1041 (4)	0.0622 (3)	0.0482 (2)	−0.0037 (2)	0.0024 (2)	0.00406 (17)

C1—N1	1.463 (2)	C6—H6A	0.97
C1—H1A	0.96	C6—H6B	0.97
C1—H1B	0.96	C7—C8	1.474 (2)
C1—H1C	0.96	C7—H7	0.93
C2—N1	1.458 (2)	C8—C13	1.400 (2)
C2—C3	1.514 (3)	C8—C9	1.403 (2)
C2—H2A	0.97	C9—C10	1.385 (2)
C2—H2B	0.97	C9—Cl1	1.7440 (15)
C3—C4	1.501 (3)	C10—C11	1.385 (2)
C3—H3A	0.97	C10—H10	0.93
C3—H3B	0.97	C11—C12	1.380 (2)
C4—O1	1.209 (2)	C11—Cl2	1.7435 (15)
C4—C5	1.504 (2)	C12—C13	1.388 (2)
C5—C7	1.346 (2)	C12—H12	0.93
C5—C6	1.510 (2)	C13—H13	0.93
C6—N1	1.465 (2)
N1—C1—H1A	109.5	N1—C6—H6B	109.3
N1—C1—H1B	109.5	C5—C6—H6B	109.3
H1A—C1—H1B	109.5	H6A—C6—H6B	107.9
N1—C1—H1C	109.5	C5—C7—C8	126.95 (15)
H1A—C1—H1C	109.5	C5—C7—H7	116.5
H1B—C1—H1C	109.5	C8—C7—H7	116.5
N1—C2—C3	110.39 (15)	C13—C8—C9	116.34 (13)
N1—C2—H2A	109.6	C13—C8—C7	122.59 (14)
C3—C2—H2A	109.6	C9—C8—C7	121.07 (14)
N1—C2—H2B	109.6	C10—C9—C8	122.94 (13)
C3—C2—H2B	109.6	C10—C9—Cl1	117.27 (11)
H2A—C2—H2B	108.1	C8—C9—Cl1	119.78 (12)
C4—C3—C2	114.99 (16)	C11—C10—C9	117.82 (13)
C4—C3—H3A	108.5	C11—C10—H10	121.1
C2—C3—H3A	108.5	C9—C10—H10	121.1
C4—C3—H3B	108.5	C12—C11—C10	121.83 (14)
C2—C3—H3B	108.5	C12—C11—Cl2	119.47 (12)
H3A—C3—H3B	107.5	C10—C11—Cl2	118.69 (12)
O1—C4—C5	121.85 (17)	C11—C12—C13	118.85 (15)
O1—C4—C3	120.41 (16)	C11—C12—H12	120.6
C5—C4—C3	117.69 (16)	C13—C12—H12	120.6
C7—C5—C4	116.86 (16)	C12—C13—C8	121.99 (14)
C7—C5—C6	125.39 (14)	C12—C13—H13	119.0
C4—C5—C6	117.70 (14)	C8—C13—H13	119.0
N1—C6—C5	111.81 (13)	C1—N1—C2	110.56 (15)
N1—C6—H6A	109.3	C1—N1—C6	109.51 (14)
C5—C6—H6A	109.3	C2—N1—C6	109.96 (13)
N1—C2—C3—C4	−46.3 (2)	C13—C8—C9—Cl1	−176.27 (11)
C2—C3—C4—O1	−161.3 (2)	C7—C8—C9—Cl1	3.54 (19)
C2—C3—C4—C5	21.1 (3)	C8—C9—C10—C11	−2.0 (2)
O1—C4—C5—C7	−15.5 (3)	Cl1—C9—C10—C11	179.32 (11)
C3—C4—C5—C7	162.09 (18)	C9—C10—C11—C12	−2.4 (2)
O1—C4—C5—C6	167.14 (19)	C9—C10—C11—Cl2	178.30 (11)
C3—C4—C5—C6	−15.2 (2)	C10—C11—C12—C13	3.4 (2)
C7—C5—C6—N1	−142.95 (16)	Cl2—C11—C12—C13	−177.33 (13)
C4—C5—C6—N1	34.12 (19)	C11—C12—C13—C8	0.0 (2)
C4—C5—C7—C8	−177.87 (14)	C9—C8—C13—C12	−4.0 (2)
C6—C5—C7—C8	−0.8 (3)	C7—C8—C13—C12	176.22 (14)
C5—C7—C8—C13	−38.6 (2)	C3—C2—N1—C1	−172.10 (17)
C5—C7—C8—C9	141.58 (17)	C3—C2—N1—C6	66.9 (2)
C13—C8—C9—C10	5.0 (2)	C5—C6—N1—C1	178.07 (14)
C7—C8—C9—C10	−175.16 (13)	C5—C6—N1—C2	−60.26 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1i	0.93	2.46	3.366 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1i	0.93	2.46	3.366 (2)	163

Symmetry code: (i) .