1-Chloro-2-(4-phenyl-piperazin-1-yl)ethanone.

The title compound, C(12)H(15)ClN(2)O, is a piperazine derivative with the potential for use as a starting material for pharmaceutial and agrochemical applications. The structure is stabilized by C-H⋯O hydrogen bonds, C-H⋯π inter-actions and π-π stacking inter-actions [centroid-centroid distance = is 4.760 (2) Å].

Related literature

For the biological activity of piperazine and its derivatives, see: Berkheij (2005 ▶); Upadhayaya et al. (2004 ▶); Choudhary et al. (2006 ▶); Vacca et al. (1994 ▶); Hulme (1999 ▶). For reference structural data, see: Drew & Leslie (1986 ▶).

Experimental

Crystal data

C12H15ClN2O

M = 238.71

Monoclinic,

a = 9.4423 (19) Å

b = 8.5629 (17) Å

c = 14.506 (3) Å

β = 101.34 (3)°

V = 1149.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 113 K

0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.940, T max = 0.964

9264 measured reflections

2729 independent reflections

2151 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.098

S = 1.07

2729 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809008216/hg2461sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008216/hg2461Isup2.hkl

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

C12H15ClN2O	F(000) = 504
Mr = 238.71	Dx = 1.379 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3260 reflections
a = 9.4423 (19) Å	θ = 3.2–27.9°
b = 8.5629 (17) Å	µ = 0.31 mm−1
c = 14.506 (3) Å	T = 113 K
β = 101.34 (3)°	Block, colourless
V = 1149.9 (4) Å3	0.20 × 0.18 × 0.12 mm
Z = 4

Rigaku Saturn diffractometer	2729 independent reflections
Radiation source: rotating anode	2151 reflections with I > 2σ(I)
confocal	Rint = 0.035
ω scans	θmax = 27.9°, θmin = 3.2°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −12→12
Tmin = 0.940, Tmax = 0.964	k = −8→11
9264 measured reflections	l = −16→19

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.055P)2 + 0.0763P] where P = (Fo2 + 2Fc2)/3
2729 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.26 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
Cl1	0.62862 (4)	0.03256 (4)	0.08928 (2)	0.03631 (13)
O1	0.58185 (10)	−0.16571 (10)	0.24044 (7)	0.0297 (2)
N1	0.75320 (11)	0.03812 (12)	0.56187 (8)	0.0237 (2)
N2	0.66086 (12)	−0.00754 (12)	0.36497 (8)	0.0244 (2)
C1	0.82553 (13)	0.04592 (14)	0.65699 (10)	0.0230 (3)
C2	0.76046 (14)	−0.02277 (14)	0.72590 (10)	0.0276 (3)
H2	0.6724	−0.0739	0.7082	0.033*
C3	0.82561 (16)	−0.01541 (15)	0.81981 (11)	0.0312 (3)
H3	0.7815	−0.0627	0.8646	0.037*
C4	0.95649 (16)	0.06196 (16)	0.84812 (10)	0.0311 (3)
H4	1.0004	0.0664	0.9113	0.037*
C5	1.02012 (14)	0.13211 (15)	0.78058 (10)	0.0299 (3)
H5	1.1069	0.1854	0.7989	0.036*
C6	0.95647 (13)	0.12419 (15)	0.68604 (10)	0.0253 (3)
H6	1.0013	0.1714	0.6416	0.030*
C7	0.80673 (14)	0.13837 (14)	0.49496 (10)	0.0256 (3)
H7A	0.8961	0.0961	0.4821	0.031*
H7B	0.8263	0.2419	0.5215	0.031*
C8	0.69545 (14)	0.14856 (14)	0.40466 (10)	0.0266 (3)
H8A	0.6084	0.1975	0.4170	0.032*
H8B	0.7325	0.2128	0.3597	0.032*
C9	0.61886 (13)	−0.11941 (14)	0.43097 (10)	0.0250 (3)
H9A	0.6128	−0.2231	0.4035	0.030*
H9B	0.5242	−0.0921	0.4425	0.030*
C10	0.72706 (13)	−0.12050 (14)	0.52343 (10)	0.0256 (3)
H10A	0.6908	−0.1857	0.5683	0.031*
H10B	0.8174	−0.1650	0.5137	0.031*
C11	0.63200 (13)	−0.03982 (14)	0.27233 (10)	0.0237 (3)
C12	0.66787 (14)	0.08973 (15)	0.20873 (9)	0.0272 (3)
H12A	0.7695	0.1158	0.2266	0.033*
H12B	0.6124	0.1823	0.2169	0.033*

	U11	U22	U33	U12	U13	U23
Cl1	0.0485 (2)	0.0282 (2)	0.0289 (2)	0.00339 (14)	−0.00042 (16)	−0.00073 (13)
O1	0.0291 (5)	0.0214 (5)	0.0375 (6)	−0.0028 (4)	0.0034 (4)	−0.0060 (4)
N1	0.0219 (5)	0.0164 (5)	0.0314 (6)	−0.0042 (4)	0.0021 (4)	0.0009 (4)
N2	0.0241 (5)	0.0174 (5)	0.0309 (6)	−0.0036 (4)	0.0033 (4)	−0.0005 (4)
C1	0.0199 (6)	0.0161 (6)	0.0319 (7)	0.0025 (4)	0.0027 (5)	0.0008 (5)
C2	0.0236 (6)	0.0199 (6)	0.0396 (8)	−0.0006 (5)	0.0072 (6)	0.0022 (5)
C3	0.0358 (7)	0.0233 (7)	0.0360 (8)	0.0027 (6)	0.0105 (6)	0.0043 (6)
C4	0.0359 (7)	0.0263 (7)	0.0293 (8)	0.0046 (6)	0.0021 (6)	−0.0028 (6)
C5	0.0261 (7)	0.0254 (7)	0.0364 (8)	−0.0013 (5)	0.0016 (6)	−0.0042 (6)
C6	0.0222 (6)	0.0210 (6)	0.0325 (8)	−0.0023 (5)	0.0047 (5)	−0.0005 (5)
C7	0.0242 (6)	0.0181 (6)	0.0333 (8)	−0.0051 (5)	0.0028 (5)	0.0003 (5)
C8	0.0306 (7)	0.0164 (6)	0.0314 (7)	−0.0031 (5)	0.0026 (6)	−0.0005 (5)
C9	0.0228 (6)	0.0169 (6)	0.0348 (8)	−0.0049 (5)	0.0048 (5)	−0.0006 (5)
C10	0.0220 (6)	0.0160 (6)	0.0375 (8)	−0.0023 (5)	0.0031 (5)	0.0013 (5)
C11	0.0165 (6)	0.0193 (6)	0.0341 (7)	0.0031 (5)	0.0022 (5)	−0.0011 (5)
C12	0.0280 (7)	0.0220 (6)	0.0291 (7)	0.0016 (5)	−0.0004 (5)	−0.0014 (5)

Cl1—C12	1.7682 (14)	C5—C6	1.386 (2)
O1—C11	1.2304 (15)	C5—H5	0.9300
N1—C1	1.4157 (18)	C6—H6	0.9300
N1—C7	1.4586 (16)	C7—C8	1.5119 (18)
N1—C10	1.4705 (16)	C7—H7A	0.9700
N2—C11	1.3463 (18)	C7—H7B	0.9700
N2—C9	1.4632 (17)	C8—H8A	0.9700
N2—C8	1.4666 (15)	C8—H8B	0.9700
C1—C6	1.3965 (18)	C9—C10	1.5177 (18)
C1—C2	1.4015 (19)	C9—H9A	0.9700
C2—C3	1.381 (2)	C9—H9B	0.9700
C2—H2	0.9300	C10—H10A	0.9700
C3—C4	1.391 (2)	C10—H10B	0.9700
C3—H3	0.9300	C11—C12	1.5229 (18)
C4—C5	1.383 (2)	C12—H12A	0.9700
C4—H4	0.9300	C12—H12B	0.9700
C1—N1—C7	117.19 (10)	H7A—C7—H7B	108.2
C1—N1—C10	115.21 (10)	N2—C8—C7	110.53 (10)
C7—N1—C10	110.21 (11)	N2—C8—H8A	109.5
C11—N2—C9	119.41 (10)	C7—C8—H8A	109.5
C11—N2—C8	124.38 (11)	N2—C8—H8B	109.5
C9—N2—C8	114.07 (11)	C7—C8—H8B	109.5
C6—C1—C2	118.20 (13)	H8A—C8—H8B	108.1
C6—C1—N1	123.06 (12)	N2—C9—C10	111.12 (10)
C2—C1—N1	118.70 (11)	N2—C9—H9A	109.4
C3—C2—C1	120.76 (13)	C10—C9—H9A	109.4
C3—C2—H2	119.6	N2—C9—H9B	109.4
C1—C2—H2	119.6	C10—C9—H9B	109.4
C2—C3—C4	120.68 (13)	H9A—C9—H9B	108.0
C2—C3—H3	119.7	N1—C10—C9	111.28 (10)
C4—C3—H3	119.7	N1—C10—H10A	109.4
C5—C4—C3	118.83 (14)	C9—C10—H10A	109.4
C5—C4—H4	120.6	N1—C10—H10B	109.4
C3—C4—H4	120.6	C9—C10—H10B	109.4
C4—C5—C6	121.01 (13)	H10A—C10—H10B	108.0
C4—C5—H5	119.5	O1—C11—N2	122.85 (12)
C6—C5—H5	119.5	O1—C11—C12	121.70 (12)
C5—C6—C1	120.52 (13)	N2—C11—C12	115.44 (10)
C5—C6—H6	119.7	C11—C12—Cl1	111.30 (9)
C1—C6—H6	119.7	C11—C12—H12A	109.4
N1—C7—C8	109.74 (11)	Cl1—C12—H12A	109.4
N1—C7—H7A	109.7	C11—C12—H12B	109.4
C8—C7—H7A	109.7	Cl1—C12—H12B	109.4
N1—C7—H7B	109.7	H12A—C12—H12B	108.0
C8—C7—H7B	109.7
C7—N1—C1—C6	−10.51 (17)	C11—N2—C8—C7	−143.92 (12)
C10—N1—C1—C6	121.65 (13)	C9—N2—C8—C7	52.87 (14)
C7—N1—C1—C2	166.96 (11)	N1—C7—C8—N2	−57.54 (14)
C10—N1—C1—C2	−60.88 (15)	C11—N2—C9—C10	145.88 (11)
C6—C1—C2—C3	−1.11 (18)	C8—N2—C9—C10	−50.00 (14)
N1—C1—C2—C3	−178.71 (11)	C1—N1—C10—C9	166.07 (10)
C1—C2—C3—C4	0.7 (2)	C7—N1—C10—C9	−58.57 (13)
C2—C3—C4—C5	0.3 (2)	N2—C9—C10—N1	52.08 (14)
C3—C4—C5—C6	−0.9 (2)	C9—N2—C11—O1	−6.05 (18)
C4—C5—C6—C1	0.5 (2)	C8—N2—C11—O1	−168.43 (12)
C2—C1—C6—C5	0.48 (19)	C9—N2—C11—C12	174.87 (11)
N1—C1—C6—C5	177.96 (11)	C8—N2—C11—C12	12.49 (17)
C1—N1—C7—C8	−164.61 (10)	O1—C11—C12—Cl1	−0.20 (15)
C10—N1—C7—C8	61.01 (13)	N2—C11—C12—Cl1	178.89 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1i	0.93	2.47	3.1850 (16)	134
C9—H9A···O1	0.97	2.38	2.7456 (17)	102
C12—H12B···O1ii	0.97	2.43	3.3426 (16)	157
C5—H5···Cg2iii	0.93	3.25	3.7651 (15)	117
C8—H8B···Cg2iv	0.97	3.09	4.0393 (12)	168
C12—H12A···Cg2iv	0.97	3.04	3.6878	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1i	0.93	2.47	3.1850 (16)	134
C9—H9A⋯O1	0.97	2.38	2.7456 (17)	102
C12—H12B⋯O1ii	0.97	2.43	3.3426 (16)	157
C5—H5⋯Cg2iii	0.93	3.25	3.7651 (15)	117
C8—H8B⋯Cg2iv	0.97	3.09	4.0393 (12)	168
C12—H12A⋯Cg2iv	0.97	3.04	3.6878	125

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg2 is the centroid of the C1–C6 ring.