2-Chloro-1-[4-(2-fluoro-benz-yl)piperazin-1-yl]ethanone.

In the title compound, C(13)H(16)ClFN(2)O, the piperazine ring is flanked by 1-(2-fluoro-benz-yl)piperazine and adopts a chair conformation. The dihedral angle between the fluoro-phenyl ring and the four planar C atoms (r.m.s. = 0.0055 Å) of the piperazine chair is 78.27 (7)°, whereas the dihedral angle between the four planar C atoms of the piperazine chair and the ethanone plane is 55.21 (9) Å; the Cl atom displaced by1.589 (2) Å out of the plane.

Related literature

For the synthesis of related compounds, see: Contreras et al. (2001 ▶); Capuano et al. (2002 ▶). For their use as inter­mediates in the synthesis of anti-inflammatory agents or CCR1 antagonists, see: Rolland & Duhault (1989 ▶); Kaufmann (2005 ▶); Tanikawa et al. (1995 ▶); Xie et al. (2007 ▶).

Experimental

Crystal data

C13H16ClFN2O

M = 270.73

Orthorhombic,

a = 7.9350 (5) Å

b = 8.4610 (4) Å

c = 19.0040 (11) Å

V = 1275.89 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 291 K

0.30 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.566, T max = 0.716

12886 measured reflections

3001 independent reflections

2550 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.085

S = 1.01

3001 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶), 1255 Friedel pairs

Flack parameter: 0.03 (7)

Data collection: APEX2 (Bruker, 2003 ▶); 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: DIAMOND (Brandenburg, 1999) ▶; software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811006180/si2316sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006180/si2316Isup2.hkl

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

C13H16ClFN2O	F(000) = 568
Mr = 270.73	Dx = 1.409 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 7.9350 (5) Å	θ = 7.5–15°
b = 8.4610 (4) Å	µ = 0.30 mm−1
c = 19.0040 (11) Å	T = 291 K
V = 1275.89 (12) Å3	Block, colorless
Z = 4	0.30 × 0.30 × 0.20 mm

Bruker APEXII CCD diffractometer	3001 independent reflections
Radiation source: fine-focus sealed tube	2550 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω scans	θmax = 28.4°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
Tmin = 0.566, Tmax = 0.716	k = −10→10
12886 measured reflections	l = −25→25

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.035	w = 1/[σ2(Fo2) + (0.028P)2 + 0.4P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.085	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.33 e Å−3
3001 reflections	Δρmin = −0.18 e Å−3
165 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.077 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1255 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.03 (7)

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
O1	1.51486 (16)	0.40256 (17)	0.67832 (8)	0.0512 (3)
Cl1	1.23456 (9)	0.09826 (6)	0.64207 (3)	0.06647 (19)
F1	0.6313 (2)	0.88072 (19)	0.64912 (8)	0.0801 (4)
N1	0.96049 (18)	0.62572 (16)	0.64509 (8)	0.0378 (3)
N2	1.2433 (2)	0.46187 (17)	0.70180 (8)	0.0437 (4)
C1	0.8356 (2)	0.8253 (2)	0.56706 (9)	0.0415 (4)
C2	0.7317 (3)	0.9332 (2)	0.59859 (10)	0.0492 (5)
C3	0.7224 (3)	1.0901 (3)	0.58058 (12)	0.0622 (6)
H3	0.6497	1.1582	0.6041	0.075*
C4	0.8215 (3)	1.1433 (3)	0.52783 (12)	0.0623 (6)
H4	0.8177	1.2491	0.5146	0.075*
C5	0.9276 (3)	1.0405 (3)	0.49380 (12)	0.0588 (6)
H5	0.9960	1.0766	0.4574	0.071*
C6	0.9328 (3)	0.8832 (3)	0.51363 (10)	0.0524 (5)
H6	1.0047	0.8148	0.4898	0.063*
C7	0.8427 (2)	0.6546 (2)	0.58860 (10)	0.0459 (4)
H7A	0.7312	0.6211	0.6034	0.055*
H7B	0.8746	0.5912	0.5482	0.055*
C8	1.1333 (2)	0.6613 (2)	0.62433 (10)	0.0424 (4)
H8A	1.1409	0.7723	0.6118	0.051*
H8B	1.1613	0.6000	0.5828	0.051*
C9	1.2590 (2)	0.6266 (2)	0.68052 (10)	0.0459 (4)
H9A	1.3719	0.6464	0.6631	0.055*
H9B	1.2395	0.6951	0.7207	0.055*
C10	1.0718 (2)	0.4225 (3)	0.72213 (11)	0.0500 (5)
H10A	1.0413	0.4821	0.7638	0.060*
H10B	1.0655	0.3109	0.7336	0.060*
C11	0.9506 (2)	0.4583 (2)	0.66487 (11)	0.0460 (5)
H11A	0.9758	0.3931	0.6242	0.055*
H11B	0.8372	0.4337	0.6804	0.055*
C12	1.3729 (2)	0.3613 (2)	0.69620 (9)	0.0388 (4)
C13	1.3417 (3)	0.1882 (2)	0.71208 (10)	0.0476 (5)
H13A	1.2753	0.1787	0.7547	0.057*
H13B	1.4484	0.1351	0.7197	0.057*

	U11	U22	U33	U12	U13	U23
O1	0.0326 (7)	0.0537 (8)	0.0671 (9)	0.0000 (6)	−0.0001 (6)	0.0034 (7)
Cl1	0.0760 (4)	0.0506 (3)	0.0729 (3)	−0.0109 (3)	−0.0059 (3)	−0.0099 (3)
F1	0.0805 (10)	0.0910 (10)	0.0688 (8)	0.0264 (8)	0.0272 (8)	0.0187 (8)
N1	0.0326 (7)	0.0339 (7)	0.0471 (8)	0.0024 (6)	−0.0027 (6)	0.0003 (6)
N2	0.0343 (8)	0.0416 (7)	0.0552 (9)	0.0042 (7)	0.0010 (8)	0.0090 (6)
C1	0.0373 (9)	0.0480 (10)	0.0393 (9)	0.0030 (8)	−0.0091 (7)	−0.0007 (8)
C2	0.0465 (11)	0.0587 (12)	0.0423 (9)	0.0063 (10)	−0.0002 (9)	0.0045 (8)
C3	0.0751 (15)	0.0544 (11)	0.0573 (12)	0.0190 (12)	0.0006 (12)	−0.0014 (10)
C4	0.0801 (17)	0.0479 (12)	0.0590 (13)	−0.0008 (11)	−0.0167 (11)	0.0099 (10)
C5	0.0596 (14)	0.0677 (14)	0.0492 (11)	−0.0068 (11)	−0.0017 (10)	0.0128 (10)
C6	0.0502 (11)	0.0624 (13)	0.0447 (10)	0.0049 (10)	−0.0006 (9)	−0.0006 (10)
C7	0.0400 (10)	0.0464 (10)	0.0512 (10)	−0.0017 (8)	−0.0089 (9)	−0.0047 (9)
C8	0.0363 (9)	0.0337 (8)	0.0570 (11)	−0.0023 (7)	−0.0006 (8)	0.0053 (8)
C9	0.0370 (9)	0.0362 (9)	0.0645 (11)	−0.0006 (8)	−0.0076 (9)	0.0016 (8)
C10	0.0393 (11)	0.0497 (11)	0.0610 (12)	0.0068 (8)	0.0094 (9)	0.0158 (10)
C11	0.0328 (9)	0.0397 (9)	0.0656 (13)	−0.0015 (8)	0.0056 (9)	0.0061 (9)
C12	0.0364 (9)	0.0433 (9)	0.0366 (8)	0.0023 (8)	−0.0050 (7)	−0.0010 (7)
C13	0.0479 (11)	0.0442 (11)	0.0506 (11)	0.0067 (9)	−0.0049 (9)	0.0071 (9)

O1—C12	1.228 (2)	C5—H5	0.9300
Cl1—C13	1.753 (2)	C6—H6	0.9300
F1—C2	1.324 (2)	C7—H7A	0.9700
N1—C7	1.444 (2)	C7—H7B	0.9700
N1—C8	1.459 (2)	C8—C9	1.490 (3)
N1—C11	1.467 (2)	C8—H8A	0.9700
N2—C12	1.339 (2)	C8—H8B	0.9700
N2—C10	1.454 (2)	C9—H9A	0.9700
N2—C9	1.457 (2)	C9—H9B	0.9700
C1—C6	1.366 (3)	C10—C11	1.483 (3)
C1—C2	1.369 (3)	C10—H10A	0.9700
C1—C7	1.502 (3)	C10—H10B	0.9700
C2—C3	1.373 (3)	C11—H11A	0.9700
C3—C4	1.351 (3)	C11—H11B	0.9700
C3—H3	0.9300	C12—C13	1.515 (3)
C4—C5	1.373 (3)	C13—H13A	0.9700
C4—H4	0.9300	C13—H13B	0.9700
C5—C6	1.384 (3)
C7—N1—C8	111.87 (15)	C9—C8—H8A	108.9
C7—N1—C11	108.62 (14)	N1—C8—H8B	108.9
C8—N1—C11	108.59 (13)	C9—C8—H8B	108.9
C12—N2—C10	126.45 (15)	H8A—C8—H8B	107.7
C12—N2—C9	121.38 (16)	N2—C9—C8	109.27 (15)
C10—N2—C9	111.92 (15)	N2—C9—H9A	109.8
C6—C1—C2	115.21 (18)	C8—C9—H9A	109.8
C6—C1—C7	121.77 (18)	N2—C9—H9B	109.8
C2—C1—C7	123.02 (18)	C8—C9—H9B	109.8
F1—C2—C1	117.11 (18)	H9A—C9—H9B	108.3
F1—C2—C3	118.22 (19)	N2—C10—C11	111.40 (16)
C1—C2—C3	124.7 (2)	N2—C10—H10A	109.3
C4—C3—C2	118.4 (2)	C11—C10—H10A	109.3
C4—C3—H3	120.8	N2—C10—H10B	109.3
C2—C3—H3	120.8	C11—C10—H10B	109.3
C3—C4—C5	119.7 (2)	H10A—C10—H10B	108.0
C3—C4—H4	120.2	N1—C11—C10	110.55 (16)
C5—C4—H4	120.2	N1—C11—H11A	109.5
C4—C5—C6	120.0 (2)	C10—C11—H11A	109.5
C4—C5—H5	120.0	N1—C11—H11B	109.5
C6—C5—H5	120.0	C10—C11—H11B	109.5
C1—C6—C5	122.1 (2)	H11A—C11—H11B	108.1
C1—C6—H6	119.0	O1—C12—N2	123.07 (18)
C5—C6—H6	119.0	O1—C12—C13	118.68 (17)
N1—C7—C1	112.92 (15)	N2—C12—C13	118.24 (17)
N1—C7—H7A	109.0	C12—C13—Cl1	110.34 (13)
C1—C7—H7A	109.0	C12—C13—H13A	109.6
N1—C7—H7B	109.0	Cl1—C13—H13A	109.6
C1—C7—H7B	109.0	C12—C13—H13B	109.6
H7A—C7—H7B	107.8	Cl1—C13—H13B	109.6
N1—C8—C9	113.25 (16)	H13A—C13—H13B	108.1
N1—C8—H8A	108.9
C6—C1—C2—F1	177.86 (18)	C11—N1—C8—C9	−57.8 (2)
C7—C1—C2—F1	−1.6 (3)	C12—N2—C9—C8	120.59 (19)
C6—C1—C2—C3	−0.9 (3)	C10—N2—C9—C8	−54.0 (2)
C7—C1—C2—C3	179.7 (2)	N1—C8—C9—N2	56.1 (2)
F1—C2—C3—C4	−178.3 (2)	C12—N2—C10—C11	−118.1 (2)
C1—C2—C3—C4	0.4 (3)	C9—N2—C10—C11	56.2 (2)
C2—C3—C4—C5	0.1 (3)	C7—N1—C11—C10	179.10 (16)
C3—C4—C5—C6	0.0 (3)	C8—N1—C11—C10	57.2 (2)
C2—C1—C6—C5	0.9 (3)	N2—C10—C11—N1	−57.6 (2)
C7—C1—C6—C5	−179.60 (19)	C10—N2—C12—O1	179.59 (18)
C4—C5—C6—C1	−0.5 (3)	C9—N2—C12—O1	5.8 (3)
C8—N1—C7—C1	−63.4 (2)	C10—N2—C12—C13	0.2 (3)
C11—N1—C7—C1	176.72 (16)	C9—N2—C12—C13	−173.64 (16)
C6—C1—C7—N1	93.1 (2)	O1—C12—C13—Cl1	−103.48 (18)
C2—C1—C7—N1	−87.4 (2)	N2—C12—C13—Cl1	75.97 (19)
C7—N1—C8—C9	−177.68 (15)