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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...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037300/bt2456sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037300/bt2456Isup2.hkl
Contains datablock I

CCDC reference: 660198

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.132
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 200 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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).

Structure description 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).

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

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
C18H16Cl2N2O2F(000) = 752
Mr = 363.23Dx = 1.415 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1786 reflections
a = 11.892 (2) Åθ = 2.5–26.2°
b = 11.413 (2) ŵ = 0.39 mm1
c = 12.653 (2) ÅT = 294 K
β = 96.959 (3)°Block, 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)
Graphite monochromatorRint = 0.044
φ and ω scansθmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.940, Tmax = 0.954k = 714
9538 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0605P)2 + 0.0445P]
where P = (Fo2 + 2Fc2)/3
3473 reflections(Δ/σ)max = 0.002
217 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C18H16Cl2N2O2V = 1704.6 (5) Å3
Mr = 363.23Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.892 (2) ŵ = 0.39 mm1
b = 11.413 (2) ÅT = 294 K
c = 12.653 (2) Å0.16 × 0.14 × 0.12 mm
β = 96.959 (3)°
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)] = 0.0430 restraints
wR(F2) = 0.132H-atom parameters constrained
S = 1.00Δρmax = 0.37 e Å3
3473 reflectionsΔρmin = 0.22 e Å3
217 parameters
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 > 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.

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)
C40.0192 (2)0.9316 (2)0.3633 (2)0.0524 (7)
H40.08160.97250.38190.063*
C50.0182 (2)0.8109 (2)0.3649 (2)0.0462 (7)
H50.08030.77050.38480.055*
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, º) 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—C30.6 (4)C15—C10—C11—C121.1 (4)
C1—C2—C3—C41.4 (4)C10—C11—C12—C131.0 (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—C5178.8 (2)Cl2—C12—C13—C14178.64 (19)
C3—C4—C5—C60.1 (4)C12—C13—C14—C150.5 (4)
C4—C5—C6—C11.9 (4)C13—C14—C15—C100.4 (4)
C4—C5—C6—C7178.3 (2)C13—C14—C15—C16171.6 (2)
C2—C1—C6—C52.2 (4)C11—C10—C15—C140.5 (4)
C2—C1—C6—C7178.8 (2)C11—C10—C15—C16172.9 (2)
C9—N1—C7—O14.5 (4)C17—N2—C16—O2166.5 (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—C619.6 (4)C18—N2—C16—C15175.3 (2)
C5—C6—C7—O1127.9 (3)C14—C15—C16—O2124.8 (3)
C1—C6—C7—O148.6 (3)C10—C15—C16—O247.3 (3)
C5—C6—C7—N151.5 (3)C14—C15—C16—N254.3 (4)
C1—C6—C7—N1132.0 (2)C10—C15—C16—N2133.6 (3)
C7—N1—C8—C9i136.7 (2)C16—N2—C17—C18ii131.6 (3)
C9—N1—C8—C9i57.0 (3)C18—N2—C17—C18ii57.6 (3)
C7—N1—C9—C8i136.4 (2)C16—N2—C18—C17ii131.4 (3)
C8—N1—C9—C8i56.2 (3)C17—N2—C18—C17ii57.1 (3)
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) 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.

Experimental details

Crystal data
Chemical formulaC18H16Cl2N2O2
Mr363.23
Crystal system, space groupMonoclinic, P21/n
Temperature (K)294
a, b, c (Å)11.892 (2), 11.413 (2), 12.653 (2)
β (°) 96.959 (3)
V3)1704.6 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.39
Crystal size (mm)0.16 × 0.14 × 0.12
Data collection
DiffractometerBruker SMART 1K CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.940, 0.954
No. of measured, independent and
observed [I > 2σ(I)] reflections
9538, 3473, 1795
Rint0.044
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.132, 1.00
No. of reflections3473
No. of parameters217
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.22

Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) 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.
 

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