Download citation
Download citation
link to html
The mol­ecule of the title compound, C18H10F8N2O2, is located on an inversion center. The piperazine ring adopts a chair conformation and the two tetra­fluoro­phenyl rings are strictly parallel to each other. The mol­ecules are connected by C—H...O hydrogen bonds into a one-dimensional chain-like supra­molecular structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046776/is2210sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046776/is2210Isup2.hkl
Contains datablock I

CCDC reference: 663847

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.039
  • wR factor = 0.109
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level G PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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

Recently, the supramolecular structures of systems containing piperazine unit, which includes both of hydrogen-bonded systems and of metal coordination complexes, have been extensively studied. (Kartha et al., 1981; Luo & Palmore, 2002; Varughese & Kartha, 1982). To date, many piperazine derivatives with various substitutes have been synthesized (Zheng et al., 2005; Sarangarajan et al., 2005). Herein, we report the structure of a new compound N,N'-bis(2,3,4,5-tetrafluorobenzoyl)piperazine (I).

The geometry and labeling scheme of the title compound are depicted in Figure 1. The compound is a centrosymmetric compound N,N'-bis(2,3,4,5-tetrafluorobenzoyl)piperazine. The piperazine ring adopts a chair conformation and the two tetrafluorophenyl rings are strict parallel to each other due to the centrosymmetry. All atoms from tetrafluorophenyl ring is nearly strict planar with the largest deviation of 0.0105 (18) Å from the mean plane. The carbonyl group bond distance is 1.2275 (18) Å for C7—O1 and the amide bond distance is 1.3409 (19) Å for C7—N1, which are very similar to those of its derivative N,N'-dibenzoylpiperazine (Zheng et al., 2005). The C—F bond lengths range from 1.334 (2) to 1.334 (2) Å.

In the title compound, the N,N'-bis(2,3,4,5-tetrafluorobenzoyl)piperazine units were connected together by the intermolecular C—H···O hydrogen bonds, leading to a one-dimensional chain-like supramolecular structure as shown in Figure 2.

Related literature top

For related literature, see: Kartha et al. (1981); Luo & Palmore (2002); Sarangarajan et al. (2005); Varughese & Kartha (1982); Zheng et al. (2005).

Experimental top

The title compound N,N'-bis(2,3,4,5-tetrafluorobenzoyl) piperazine was synthesized by the reaction of tetrafluorobenzoyl chloride (1.4 g, 10 mmol) with piperazine (0.42 g, 5 mmol) in the presence of triethylamine (1.01 g, 10 mmol) in ethanol (50 ml). Colorless block crystals were obtained by recrystallization from an ethanol solution (yield 80%). Elemental analysis, calculated for C18H10F8N2O2: C 49.33, H 2.30, N 6.39%; found: C 49.26, H 2.28, N 6.30%.

Refinement top

H atoms were located in a difference map and were refined as riding, with C—H = 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C).

Structure description top

Recently, the supramolecular structures of systems containing piperazine unit, which includes both of hydrogen-bonded systems and of metal coordination complexes, have been extensively studied. (Kartha et al., 1981; Luo & Palmore, 2002; Varughese & Kartha, 1982). To date, many piperazine derivatives with various substitutes have been synthesized (Zheng et al., 2005; Sarangarajan et al., 2005). Herein, we report the structure of a new compound N,N'-bis(2,3,4,5-tetrafluorobenzoyl)piperazine (I).

The geometry and labeling scheme of the title compound are depicted in Figure 1. The compound is a centrosymmetric compound N,N'-bis(2,3,4,5-tetrafluorobenzoyl)piperazine. The piperazine ring adopts a chair conformation and the two tetrafluorophenyl rings are strict parallel to each other due to the centrosymmetry. All atoms from tetrafluorophenyl ring is nearly strict planar with the largest deviation of 0.0105 (18) Å from the mean plane. The carbonyl group bond distance is 1.2275 (18) Å for C7—O1 and the amide bond distance is 1.3409 (19) Å for C7—N1, which are very similar to those of its derivative N,N'-dibenzoylpiperazine (Zheng et al., 2005). The C—F bond lengths range from 1.334 (2) to 1.334 (2) Å.

In the title compound, the N,N'-bis(2,3,4,5-tetrafluorobenzoyl)piperazine units were connected together by the intermolecular C—H···O hydrogen bonds, leading to a one-dimensional chain-like supramolecular structure as shown in Figure 2.

For related literature, see: Kartha et al. (1981); Luo & Palmore (2002); Sarangarajan et al. (2005); Varughese & Kartha (1982); Zheng et al. (2005).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1998); software used to prepare material for publication: XP (Sheldrick, 1998).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms. The suffix A corresponds to symmetry code (-x + 1/2, -y + 3/2, -z + 1).
[Figure 2] Fig. 2. A part of the crystal structure of (I), showing the one-dimensional chain-like supramolecular structure. Dashed lines indicate C—H···O hydrogen bonds. For the sake of clarity, H atoms not involved in the hydrogen bonds have been omitted. Atoms marked with asterisk (*), hash (#) and dollar ($) signs are at the symmetry positions (-x + 1/2, -y + 3/2, -z + 1), (x, y, z - 1) and (-x + 1/2, -y + 3/2, -z), respectively.
N,N'-Bis(2,3,4,5-tetrafluorobenzoyl)piperazine top
Crystal data top
C18H10F8N2O2F(000) = 880
Mr = 438.28Dx = 1.659 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1816 reflections
a = 30.158 (4) Åθ = 1.4–26.5°
b = 8.9113 (12) ŵ = 0.17 mm1
c = 6.5744 (9) ÅT = 291 K
β = 96.594 (2)°Block, colourless
V = 1755.2 (4) Å30.21 × 0.17 × 0.10 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer
1816 independent reflections
Radiation source: fine-focus sealed tube1505 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
φ and ω scansθmax = 26.5°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 3737
Tmin = 0.964, Tmax = 0.982k = 1111
6914 measured reflectionsl = 88
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0513P)2 + 0.9211P]
where P = (Fo2 + 2Fc2)/3
1816 reflections(Δ/σ)max < 0.001
136 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C18H10F8N2O2V = 1755.2 (4) Å3
Mr = 438.28Z = 4
Monoclinic, C2/cMo Kα radiation
a = 30.158 (4) ŵ = 0.17 mm1
b = 8.9113 (12) ÅT = 291 K
c = 6.5744 (9) Å0.21 × 0.17 × 0.10 mm
β = 96.594 (2)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
1816 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
1505 reflections with I > 2σ(I)
Tmin = 0.964, Tmax = 0.982Rint = 0.018
6914 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.109H-atom parameters constrained
S = 1.05Δρmax = 0.17 e Å3
1816 reflectionsΔρmin = 0.21 e Å3
136 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
F10.35977 (4)0.55322 (14)0.1733 (2)0.0882 (5)
F20.44756 (5)0.51144 (15)0.2847 (3)0.1033 (5)
F30.49652 (4)0.72402 (17)0.4995 (2)0.0858 (4)
F40.45729 (4)0.97811 (16)0.6065 (2)0.0817 (4)
O10.30498 (4)0.85478 (16)0.07758 (16)0.0567 (4)
N10.28391 (4)0.80494 (15)0.38982 (18)0.0394 (3)
C10.38334 (6)0.6604 (2)0.2813 (3)0.0540 (4)
C20.42821 (6)0.6382 (2)0.3369 (3)0.0624 (5)
C30.45290 (5)0.7449 (2)0.4468 (3)0.0566 (5)
C40.43232 (6)0.8737 (2)0.5014 (3)0.0511 (4)
C50.38765 (5)0.89670 (19)0.4480 (2)0.0454 (4)
H50.37430.98460.48700.054*
C60.36230 (5)0.78895 (17)0.3356 (2)0.0401 (4)
C70.31433 (5)0.81783 (17)0.2572 (2)0.0394 (3)
C80.23774 (5)0.84858 (19)0.3295 (2)0.0410 (4)
H8A0.23290.86230.18220.049*
H8B0.23180.94330.39360.049*
C90.29394 (5)0.76986 (19)0.6077 (2)0.0412 (4)
H9A0.29120.86010.68800.049*
H9B0.32440.73400.63470.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0746 (8)0.0620 (7)0.1262 (12)0.0065 (6)0.0041 (8)0.0388 (7)
F20.0810 (9)0.0719 (9)0.1567 (15)0.0310 (7)0.0121 (9)0.0272 (9)
F30.0411 (6)0.1097 (11)0.1053 (10)0.0177 (6)0.0028 (6)0.0016 (8)
F40.0482 (6)0.1015 (10)0.0933 (9)0.0141 (6)0.0017 (6)0.0367 (7)
O10.0500 (7)0.0867 (9)0.0341 (6)0.0045 (6)0.0081 (5)0.0078 (6)
N10.0338 (7)0.0526 (8)0.0319 (6)0.0005 (5)0.0046 (5)0.0055 (5)
C10.0522 (10)0.0468 (9)0.0638 (11)0.0052 (8)0.0103 (8)0.0084 (8)
C20.0555 (11)0.0535 (11)0.0804 (13)0.0136 (9)0.0170 (10)0.0038 (9)
C30.0374 (9)0.0736 (12)0.0596 (11)0.0064 (8)0.0095 (8)0.0056 (9)
C40.0412 (9)0.0640 (11)0.0484 (9)0.0066 (8)0.0068 (7)0.0071 (8)
C50.0417 (9)0.0508 (9)0.0448 (9)0.0009 (7)0.0099 (7)0.0076 (7)
C60.0393 (8)0.0467 (8)0.0360 (7)0.0025 (6)0.0121 (6)0.0016 (6)
C70.0409 (8)0.0431 (8)0.0348 (8)0.0057 (6)0.0068 (6)0.0014 (6)
C80.0377 (8)0.0507 (9)0.0345 (7)0.0029 (7)0.0038 (6)0.0072 (6)
C90.0356 (7)0.0561 (9)0.0317 (7)0.0019 (7)0.0025 (6)0.0043 (6)
Geometric parameters (Å, º) top
F1—C11.344 (2)C3—C41.372 (3)
F2—C21.334 (2)C4—C51.368 (2)
F3—C31.3343 (19)C5—C61.386 (2)
F4—C41.338 (2)C5—H50.9300
O1—C71.2275 (18)C6—C71.501 (2)
N1—C71.3409 (19)C8—C9i1.513 (2)
N1—C81.4563 (19)C8—H8A0.9700
N1—C91.4635 (18)C8—H8B0.9700
C1—C21.375 (3)C9—C8i1.513 (2)
C1—C61.376 (2)C9—H9A0.9700
C2—C31.363 (3)C9—H9B0.9700
C7—N1—C8120.27 (12)C1—C6—C5118.18 (15)
C7—N1—C9125.08 (13)C1—C6—C7120.56 (15)
C8—N1—C9114.04 (11)C5—C6—C7120.98 (14)
F1—C1—C2118.85 (16)O1—C7—N1123.36 (15)
F1—C1—C6119.81 (16)O1—C7—C6118.82 (13)
C2—C1—C6121.34 (17)N1—C7—C6117.81 (13)
F2—C2—C3119.90 (18)N1—C8—C9i110.70 (13)
F2—C2—C1120.01 (18)N1—C8—H8A109.5
C3—C2—C1120.09 (17)C9i—C8—H8A109.5
F3—C3—C2120.17 (18)N1—C8—H8B109.5
F3—C3—C4120.72 (18)C9i—C8—H8B109.5
C2—C3—C4119.11 (16)H8A—C8—H8B108.1
F4—C4—C5120.50 (16)N1—C9—C8i110.51 (12)
F4—C4—C3118.17 (16)N1—C9—H9A109.5
C5—C4—C3121.32 (16)C8i—C9—H9A109.5
C4—C5—C6119.97 (16)N1—C9—H9B109.5
C4—C5—H5120.0C8i—C9—H9B109.5
C6—C5—H5120.0H9A—C9—H9B108.1
F1—C1—C2—F20.4 (3)F1—C1—C6—C76.4 (2)
C6—C1—C2—F2178.96 (18)C2—C1—C6—C7174.31 (16)
F1—C1—C2—C3179.86 (18)C4—C5—C6—C10.1 (2)
C6—C1—C2—C30.5 (3)C4—C5—C6—C7173.87 (14)
F2—C2—C3—F31.1 (3)C8—N1—C7—O15.7 (2)
C1—C2—C3—F3179.42 (18)C9—N1—C7—O1176.22 (15)
F2—C2—C3—C4179.17 (18)C8—N1—C7—C6172.75 (13)
C1—C2—C3—C40.3 (3)C9—N1—C7—C62.3 (2)
F3—C3—C4—F40.7 (3)C1—C6—C7—O173.8 (2)
C2—C3—C4—F4178.98 (17)C5—C6—C7—O1100.00 (18)
F3—C3—C4—C5179.83 (16)C1—C6—C7—N1107.63 (17)
C2—C3—C4—C50.1 (3)C5—C6—C7—N178.54 (19)
F4—C4—C5—C6178.75 (15)C7—N1—C8—C9i133.86 (15)
C3—C4—C5—C60.3 (3)C9—N1—C8—C9i54.65 (19)
F1—C1—C6—C5179.64 (15)C7—N1—C9—C8i134.44 (15)
C2—C1—C6—C50.3 (3)C8—N1—C9—C8i54.55 (19)
Symmetry code: (i) x+1/2, y+3/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O1ii0.972.553.161 (2)121
Symmetry code: (ii) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC18H10F8N2O2
Mr438.28
Crystal system, space groupMonoclinic, C2/c
Temperature (K)291
a, b, c (Å)30.158 (4), 8.9113 (12), 6.5744 (9)
β (°) 96.594 (2)
V3)1755.2 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.17
Crystal size (mm)0.21 × 0.17 × 0.10
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.964, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections
6914, 1816, 1505
Rint0.018
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.109, 1.05
No. of reflections1816
No. of parameters136
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.21

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Sheldrick, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O1i0.9712.5483.161 (2)121.14
Symmetry code: (i) x, y, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds