supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers buy article online

Acta Cryst. (2007). E63, o3689    [ doi:10.1107/S1600536807037300 ]

1,4-Bis(4-chlorobenzoyl)piperazine

H.-M. Jin, P.-F. Li, C.-Y. Li and B. Liu

Abstract top

The title compound, C18H16Cl2N2O2, crystallizes with two half-molecules in the asymmetric unit; each molecule lies on an inversion centre. The piperazine ring adopts a chair conformation and the two chlorobenzene rings in each molecule are parallel to each other due to symmetry. The crystal packing is stabilized by C-H...O and C-H...[pi] interactions.

Comment top

Some amides of piperazines have been reported to exhibit marked activity in inhibiting growth of tubercle bacillus in serum (Pollard & Gray, 1953).

The title compound, C18H16Cl2N2O2, crystallizes with two half molecules in the asymmetric unit (Figs. 1 and 2).

The piperazine rings adopt a chair-conformation and the two chlorobenzene rings are parallel to each due to symmetry.

In the crystal of (I), weak C—H···O interactions (Table 1) and a C—H···π-interaction (C18···Cg1 = 3.812 (3) Å, C18—H18B···Cg1 = 155°) stabilize the structure (Cg1 is the centroid of the C1–C6 ring).

Related literature top

For related literature, see: Pollard & Gray (1953).

Experimental top

A solution of 4-chlorobenzoyl chloride in CH2Cl2 was added dropwise to a suspension of 1,4-piperazine in CH2Cl2 at room temperature with stirring. The reaction mixture continued stirring overnight. The white solid was obtained by recrystallization from methanol. Colourless blocks of (I) were grown by natural evaporation of a methanolic solution.

Refinement top

All H atoms were positioned geometrically and refined as riding atoms. The C—H distance for CH group is 0.93 Å and that CH2 group 0.97 Å both with the constraint of Uiso(H) = 1.2 Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of molecule one of the title compound with the atom-numbering scheme and 30% probability displacement ellipsoids [symmetry code: −x,-y + 1,-z + 1].
[Figure 2] Fig. 2. The molecular structure of molecule two of the title compound with the atom-numbering scheme and 30% probability displacement ellipsoids [symmetry code: −x + 1,-y + 1,-z + 1].
1,4-Bis(4-chlorobenzoyl)piperazine top
Crystal data top
C18H16Cl2N2O2F000 = 752
Mr = 363.23Dx = 1.415 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1786 reflections
a = 11.892 (2) Åθ = 2.5–26.2º
b = 11.413 (2) ŵ = 0.39 mm−1
c = 12.653 (2) ÅT = 294 (2) K
β = 96.959 (3)ºBlock, colourless
V = 1704.6 (5) Å30.16 × 0.14 × 0.12 mm
Z = 4
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		3473 independent reflections
Radiation source: fine-focus sealed tube1795 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.044
T = 294(2) Kθmax = 26.4º
φ and ω scansθmin = 2.2º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −14→14
Tmin = 0.940, Tmax = 0.954k = −7→14
9538 measured reflectionsl = −15→15
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.132  w = 1/[σ2(Fo2) + (0.0605P)2 + 0.0445P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.002
3473 reflectionsΔρmax = 0.37 e Å−3
217 parametersΔρmin = −0.21 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C18H16Cl2N2O2V = 1704.6 (5) Å3
Mr = 363.23Z = 4
Monoclinic, P21/nMo Kα
a = 11.892 (2) ŵ = 0.39 mm−1
b = 11.413 (2) ÅT = 294 (2) K
c = 12.653 (2) Å0.16 × 0.14 × 0.12 mm
β = 96.959 (3)º
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		3473 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1795 reflections with I > 2σ(I)
Tmin = 0.940, Tmax = 0.954Rint = 0.044
9538 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.043217 parameters
wR(F2) = 0.132H-atom parameters constrained
S = 1.00Δρmax = 0.37 e Å−3
3473 reflectionsΔρmin = −0.21 e Å−3
Special details top

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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.07297 (8)1.14374 (6)0.33438 (7)0.0734 (3)
Cl20.67186 (8)1.15311 (6)0.41373 (7)0.0755 (3)
O10.10101 (17)0.56724 (16)0.25514 (15)0.0608 (6)
O20.73471 (16)0.58451 (15)0.37660 (16)0.0604 (6)
N10.05304 (18)0.55966 (16)0.42159 (16)0.0431 (6)
N20.56644 (18)0.56438 (18)0.43733 (19)0.0517 (6)
C10.1649 (2)0.8111 (2)0.30465 (19)0.0445 (6)
H10.22630.77070.28350.053*
C20.1644 (2)0.9320 (2)0.3036 (2)0.0485 (7)
H20.22550.97310.28250.058*
C30.0730 (2)0.9914 (2)0.3340 (2)0.0466 (7)
C4−0.0192 (2)0.9316 (2)0.3633 (2)0.0524 (7)
H4−0.08160.97250.38190.063*
C5−0.0182 (2)0.8109 (2)0.3649 (2)0.0462 (7)
H5−0.08030.77050.38480.055*
C60.0741 (2)0.7489 (2)0.33721 (18)0.0393 (6)
C70.0774 (2)0.6181 (2)0.3351 (2)0.0407 (6)
C80.0563 (2)0.6076 (2)0.52951 (19)0.0446 (7)
H8A0.05800.69250.52640.054*
H8B0.12480.58150.57250.054*
C90.0460 (2)0.4316 (2)0.4195 (2)0.0459 (7)
H9A0.11420.39840.45780.055*
H9B0.03980.40410.34640.055*
C100.6690 (2)0.8217 (2)0.31981 (19)0.0444 (7)
H100.68190.78070.25890.053*
C110.6757 (2)0.9420 (2)0.3207 (2)0.0463 (7)
H110.69160.98250.26040.056*
C120.6586 (2)1.0017 (2)0.4119 (2)0.0443 (6)
C130.6332 (2)0.9435 (2)0.5015 (2)0.0468 (7)
H130.62150.98490.56250.056*
C140.6253 (2)0.8229 (2)0.4990 (2)0.0450 (7)
H140.60770.78300.55890.054*
C150.64333 (19)0.7606 (2)0.40892 (19)0.0386 (6)
C160.6512 (2)0.6301 (2)0.4060 (2)0.0423 (7)
C170.4532 (2)0.6053 (2)0.4531 (2)0.0516 (7)
H17A0.39840.57610.39620.062*
H17B0.45120.69020.45100.062*
C180.5771 (2)0.4364 (2)0.4426 (2)0.0574 (8)
H18A0.65420.41360.43470.069*
H18B0.52700.40090.38520.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1044 (7)0.0389 (4)0.0786 (6)−0.0003 (4)0.0184 (5)0.0003 (4)
Cl20.1046 (7)0.0373 (4)0.0892 (6)−0.0095 (4)0.0309 (5)−0.0060 (4)
O10.0898 (15)0.0487 (12)0.0508 (13)0.0040 (10)0.0366 (11)−0.0049 (9)
O20.0639 (13)0.0467 (12)0.0776 (14)0.0110 (10)0.0362 (11)0.0041 (10)
N10.0661 (15)0.0292 (11)0.0363 (13)0.0006 (10)0.0153 (11)−0.0010 (9)
N20.0502 (14)0.0316 (12)0.0789 (17)0.0098 (10)0.0300 (13)0.0082 (11)
C10.0428 (16)0.0472 (16)0.0458 (16)0.0024 (13)0.0150 (13)0.0029 (12)
C20.0487 (17)0.0471 (17)0.0503 (17)−0.0051 (14)0.0082 (14)0.0069 (13)
C30.0599 (18)0.0360 (15)0.0440 (17)−0.0011 (13)0.0068 (14)0.0022 (12)
C40.0542 (19)0.0491 (17)0.0563 (19)0.0103 (14)0.0161 (15)0.0021 (14)
C50.0457 (16)0.0434 (16)0.0525 (17)0.0016 (13)0.0183 (13)0.0040 (13)
C60.0426 (16)0.0412 (15)0.0351 (14)0.0023 (12)0.0087 (12)0.0035 (11)
C70.0455 (16)0.0395 (15)0.0393 (16)0.0025 (12)0.0138 (13)0.0011 (12)
C80.0654 (18)0.0331 (14)0.0362 (15)0.0029 (13)0.0095 (13)−0.0031 (11)
C90.0659 (19)0.0315 (14)0.0422 (16)0.0060 (13)0.0150 (14)−0.0033 (11)
C100.0545 (17)0.0417 (15)0.0396 (16)−0.0018 (13)0.0159 (13)−0.0027 (12)
C110.0534 (17)0.0451 (16)0.0418 (17)−0.0037 (13)0.0119 (13)0.0066 (13)
C120.0466 (16)0.0359 (15)0.0512 (17)−0.0031 (12)0.0098 (13)−0.0028 (13)
C130.0536 (17)0.0469 (17)0.0417 (17)0.0013 (13)0.0128 (13)−0.0107 (13)
C140.0517 (17)0.0486 (16)0.0370 (15)0.0011 (13)0.0140 (13)0.0057 (12)
C150.0391 (15)0.0375 (14)0.0403 (15)0.0010 (12)0.0090 (12)0.0013 (12)
C160.0474 (17)0.0384 (16)0.0441 (16)0.0066 (13)0.0176 (13)0.0047 (12)
C170.0524 (18)0.0352 (15)0.070 (2)0.0110 (13)0.0181 (15)0.0019 (14)
C180.0639 (19)0.0373 (16)0.076 (2)0.0132 (14)0.0274 (16)0.0037 (14)
Geometric parameters (Å, °) top
Cl1—C31.739 (3)C8—H8A0.9700
Cl2—C121.735 (3)C8—H8B0.9700
O1—C71.228 (3)C9—C8i1.513 (3)
O2—C161.219 (3)C9—H9A0.9700
N1—C71.343 (3)C9—H9B0.9700
N1—C91.464 (3)C10—C111.376 (3)
N1—C81.467 (3)C10—C151.391 (3)
N2—C161.354 (3)C10—H100.9300
N2—C171.461 (3)C11—C121.377 (3)
N2—C181.467 (3)C11—H110.9300
C1—C21.380 (3)C12—C131.378 (3)
C1—C61.395 (3)C13—C141.380 (3)
C1—H10.9300C13—H130.9300
C2—C31.375 (4)C14—C151.382 (3)
C2—H20.9300C14—H140.9300
C3—C41.380 (4)C15—C161.492 (3)
C4—C51.378 (3)C17—C18ii1.488 (4)
C4—H40.9300C17—H17A0.9700
C5—C61.387 (3)C17—H17B0.9700
C5—H50.9300C18—C17ii1.488 (4)
C6—C71.494 (3)C18—H18A0.9700
C8—C9i1.513 (3)C18—H18B0.9700
C7—N1—C9119.9 (2)N1—C9—H9B109.8
C7—N1—C8126.1 (2)C8i—C9—H9B109.8
C9—N1—C8112.61 (19)H9A—C9—H9B108.2
C16—N2—C17126.4 (2)C11—C10—C15120.8 (2)
C16—N2—C18120.1 (2)C11—C10—H10119.6
C17—N2—C18112.8 (2)C15—C10—H10119.6
C2—C1—C6120.6 (2)C10—C11—C12119.1 (2)
C2—C1—H1119.7C10—C11—H11120.5
C6—C1—H1119.7C12—C11—H11120.5
C3—C2—C1119.5 (2)C11—C12—C13121.4 (2)
C3—C2—H2120.3C11—C12—Cl2118.8 (2)
C1—C2—H2120.2C13—C12—Cl2119.8 (2)
C2—C3—C4120.9 (2)C12—C13—C14118.9 (2)
C2—C3—Cl1119.6 (2)C12—C13—H13120.6
C4—C3—Cl1119.5 (2)C14—C13—H13120.6
C5—C4—C3119.5 (3)C13—C14—C15121.0 (2)
C5—C4—H4120.3C13—C14—H14119.5
C3—C4—H4120.3C15—C14—H14119.5
C4—C5—C6120.8 (2)C14—C15—C10118.8 (2)
C4—C5—H5119.6C14—C15—C16123.4 (2)
C6—C5—H5119.6C10—C15—C16117.4 (2)
C5—C6—C1118.7 (2)O2—C16—N2121.1 (2)
C5—C6—C7122.5 (2)O2—C16—C15119.3 (2)
C1—C6—C7118.7 (2)N2—C16—C15119.6 (2)
O1—C7—N1122.0 (2)N2—C17—C18ii110.2 (2)
O1—C7—C6119.8 (2)N2—C17—H17A109.6
N1—C7—C6118.2 (2)C18ii—C17—H17A109.6
N1—C8—C9i110.8 (2)N2—C17—H17B109.6
N1—C8—H8A109.5C18ii—C17—H17B109.6
C9i—C8—H8A109.5H17A—C17—H17B108.1
N1—C8—H8B109.5N2—C18—C17ii109.3 (2)
C9i—C8—H8B109.5N2—C18—H18A109.8
H8A—C8—H8B108.1C17ii—C18—H18A109.8
N1—C9—C8i109.5 (2)N2—C18—H18B109.8
N1—C9—H9A109.8C17ii—C18—H18B109.8
C8i—C9—H9A109.8H18A—C18—H18B108.3
C6—C1—C2—C3−0.6 (4)C15—C10—C11—C121.1 (4)
C1—C2—C3—C4−1.4 (4)C10—C11—C12—C13−1.0 (4)
C1—C2—C3—Cl1179.15 (19)C10—C11—C12—Cl2177.85 (19)
C2—C3—C4—C51.7 (4)C11—C12—C13—C140.2 (4)
Cl1—C3—C4—C5−178.8 (2)Cl2—C12—C13—C14−178.64 (19)
C3—C4—C5—C6−0.1 (4)C12—C13—C14—C150.5 (4)
C4—C5—C6—C1−1.9 (4)C13—C14—C15—C10−0.4 (4)
C4—C5—C6—C7−178.3 (2)C13—C14—C15—C16171.6 (2)
C2—C1—C6—C52.2 (4)C11—C10—C15—C14−0.5 (4)
C2—C1—C6—C7178.8 (2)C11—C10—C15—C16−172.9 (2)
C9—N1—C7—O1−4.5 (4)C17—N2—C16—O2−166.5 (3)
C8—N1—C7—O1160.9 (3)C18—N2—C16—O23.8 (4)
C9—N1—C7—C6174.9 (2)C17—N2—C16—C1514.5 (4)
C8—N1—C7—C6−19.6 (4)C18—N2—C16—C15−175.3 (2)
C5—C6—C7—O1127.9 (3)C14—C15—C16—O2−124.8 (3)
C1—C6—C7—O1−48.6 (3)C10—C15—C16—O247.3 (3)
C5—C6—C7—N1−51.5 (3)C14—C15—C16—N254.3 (4)
C1—C6—C7—N1132.0 (2)C10—C15—C16—N2−133.6 (3)
C7—N1—C8—C9i136.7 (2)C16—N2—C17—C18ii−131.6 (3)
C9—N1—C8—C9i−57.0 (3)C18—N2—C17—C18ii57.6 (3)
C7—N1—C9—C8i−136.4 (2)C16—N2—C18—C17ii131.4 (3)
C8—N1—C9—C8i56.2 (3)C17—N2—C18—C17ii−57.1 (3)
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1iii0.932.423.350 (3)173
C11—H11···O2iv0.932.343.265 (3)170
C18—H18B···Cg10.97Missing3.812 (3)155
Symmetry codes: (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x+3/2, y+1/2, −z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.932.423.350 (3)173
C11—H11···O2ii0.932.343.265 (3)170
C18—H18B···Cg10.97Missing3.812 (3)155
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2.
references
References top

Bruker (1997). SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.

Pollard, C. B. & Gray, B. S. (1953). J. Am. Chem. Soc. 75, 491–491.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.