(E)-1-{4-[Bis(4-bromo­phen­yl)meth­yl]piperazin-1-yl}-3-(4-bromo­phen­yl)prop-2-en-1-one

Zhong, Y.; Zhang, X.P.; Wu, B.

doi:10.1107/S1600536811048380

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3358

https://doi.org/10.1107/S1600536811048380

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(E)-1-{4-[Bis(4-bromophenyl)methyl]piperazin-1-yl}-3-(4-bromophenyl)prop-2-en-1-one

Yan Zhong,^a XiaoPing Zhang ^b and Bin Wu ^c ^*

^aSchool of Chemistry and Chemical Engineering, Southeast University, Sipailou No. 2 Nanjing, Nanjing 210096, People's Republic of China, ^bCentre of Laboratory Animals, Nanjing Medical University, Hanzhong Road No. 140 Nanjing, Nanjing 210029, People's Republic of China, and ^cSchool of Pharmacy, Nanjing Medical University, Hanzhong Road No. 140 Nanjing, Nanjing 210029, People's Republic of China
^*Correspondence e-mail: wubin@njmu.edu.cn

(Received 31 October 2011; accepted 15 November 2011; online 19 November 2011)

In the title molecule, C₂₆H₂₃Br₃N₂O, the piperazine ring adopts a chair conformation and the C=C double bond has an E configuration. In the crystal, molecules are linked through weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For pharmacological properties of cinnamic acid derivatives, see: Shi et al. (2005 ); Qian et al. (2010 ). For the synthesis of the title compound, see: Wu et al. (2008 ). For a related structure, see: Teng et al. (2011 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₆H₂₃Br₃N₂O
M_r = 619.19
Monoclinic, P 2₁ /c
a = 9.956 (2) Å
b = 11.624 (2) Å
c = 21.310 (4) Å
β = 101.45 (3)°
V = 2417.1 (8) Å³
Z = 4
Mo Kα radiation
μ = 5.03 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.433, T_max = 0.633
4701 measured reflections
4432 independent reflections
2081 reflections with I > 2σ(I)
R_int = 0.098
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.082
S = 1.01
4432 reflections
289 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20A⋯Oⁱ	0.93	2.60	3.480 (7)	159
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811048380/pv2478sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048380/pv2478Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811048380/pv2478Isup3.cml

checkCIF report

Comment top

Recently, many compounds containing a cinnamoyl moiety have drawn much attention owing to their significant pharmacological properties such as antimicrobial, anticancer and neuroprotective activities (Shi et al., 2005; Qian et al., 2010). As a part of our ongoing study of the substituent effect on the stuctures of cinnamide derivatives, we report herein the crystal structure of the title compound.

The title compound (Fig. 1) exhibits an E configulation with respect to the C19═C20 ethene bond [1.320 (7) Å] with a torsion angle C18—C19—C20—C21 = -177.4 (6)°. The piperazine ring adopts a chair conformation with puchering parameters (Cremer & Pople, 1975) Q = 0.542 (6)Å, θ = 4.6 (6)° and φ = 157 (9)°. In the crystal, molecules are linked by intermolecular C—H···O interactions (Tab. 1, Fig. 2).

Related literature top

For pharmacological properties of cinnamic acid derivatives, see: Shi et al. (2005); Qian et al. (2010). For the synthesis of the title compound, see: Wu et al. (2008). For a related structure, see: Teng et al. (2011). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

The synthesis follows the method of Wu et al. (2008). The title compound was prepared by stirring a mixture of (E)-3-(4-bromophenyl)acrylic acid (0.908 g, 4 mmol), dimethyl sulfoxide (2 ml) and dichloromethane (30 ml) for 6 h at room temperature. The solvent was removed under reduced pressure. The residue was dissolved in acetone (15 ml) and reacted with 1-(bis(4-bromophenyl)methyl) piperazine (2.461 g, 6 mmol) in the presence of triethylamine (5 ml) for 12 h at room temperature. The resultant mixture was cooled. The title compound thus obtained was filtered and recrystallized from ethanol. The pale-yellow single crystals of the title compound used in X-ray diffraction studies were grown from a mixture of ethanol and chloroform (2:1) by slow evaporation at room temperature.

Structure description top

For pharmacological properties of cinnamic acid derivatives, see: Shi et al. (2005); Qian et al. (2010). For the synthesis of the title compound, see: Wu et al. (2008). For a related structure, see: Teng et al. (2011). For puckering parameters, see: Cremer & Pople (1975).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure and numbering scheme of the title compound; displacement ellipsoids are drawn at the 70% probability level.
	Fig. 2. A view of the unit cell of the title compound showing intermolecular and intramolecular hydrogen bonds.

(E)-1-{4-[Bis(4-bromophenyl)methyl]piperazin-1-yl}-3-(4- bromophenyl)prop-2-en-1-one top

Crystal data top

C₂₆H₂₃Br₃N₂O	F(000) = 1224
M_r = 619.19	D_x = 1.702 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 9.956 (2) Å	θ = 10–13°
b = 11.624 (2) Å	µ = 5.03 mm⁻¹
c = 21.310 (4) Å	T = 293 K
β = 101.45 (3)°	Block, pale-yellow
V = 2417.1 (8) Å³	0.20 × 0.10 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2081 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.098
Graphite monochromator	θ_max = 25.4°, θ_min = 2.0°
ω/2θ scans	h = 0→12
Absorption correction: ψ scan (North et al., 1968)	k = 0→14
T_min = 0.433, T_max = 0.633	l = −25→25
4701 measured reflections	3 standard reflections every 200 reflections
4432 independent reflections	intensity decay: 1%

Refinement top

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0185P)²] where P = (F_o² + 2F_c²)/3
4432 reflections	(Δ/σ)_max = 0.001
289 parameters	Δρ_max = 0.35 e Å⁻³
2 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₂₆H₂₃Br₃N₂O	V = 2417.1 (8) Å³
M_r = 619.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.956 (2) Å	µ = 5.03 mm⁻¹
b = 11.624 (2) Å	T = 293 K
c = 21.310 (4) Å	0.20 × 0.10 × 0.10 mm
β = 101.45 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2081 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.098
T_min = 0.433, T_max = 0.633	3 standard reflections every 200 reflections
4701 measured reflections	intensity decay: 1%
4432 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	2 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 1.01	Δρ_max = 0.35 e Å⁻³
4432 reflections	Δρ_min = −0.42 e Å⁻³
289 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

	x	y	z	U_iso*/U_eq
O	0.4281 (4)	0.8456 (3)	0.49348 (19)	0.0564 (13)
Br1	0.93912 (8)	0.12182 (7)	0.72681 (4)	0.0763 (3)
N1	0.3393 (5)	0.7165 (5)	0.5513 (3)	0.0582 (15)
C1	0.5229 (6)	0.5927 (5)	0.6057 (3)	0.059 (2)
H1A	0.5859	0.5328	0.5984	0.071*
H1B	0.5767	0.6573	0.6257	0.071*
Br2	0.16720 (8)	0.29610 (8)	0.88918 (3)	0.0834 (3)
N2	0.4370 (5)	0.5493 (4)	0.6490 (2)	0.0443 (13)
C2	0.4386 (6)	0.6302 (5)	0.5429 (3)	0.0562 (18)
H2A	0.4984	0.6611	0.5162	0.067*
H2B	0.3913	0.5641	0.5211	0.067*
Br3	−0.05208 (8)	1.44635 (7)	0.58711 (4)	0.0847 (3)
C3	0.2520 (6)	0.6816 (5)	0.5959 (3)	0.0557 (19)
H3A	0.1902	0.6210	0.5768	0.067*
H3B	0.1975	0.7465	0.6048	0.067*
C4	0.3417 (6)	0.6387 (5)	0.6579 (3)	0.0549 (18)
H4A	0.3929	0.7032	0.6795	0.066*
H4B	0.2829	0.6098	0.6856	0.066*
C5	0.5188 (6)	0.5151 (5)	0.7109 (3)	0.0510 (18)
H5A	0.5632	0.5843	0.7316	0.061*
C6	0.6277 (6)	0.4288 (5)	0.7081 (3)	0.0457 (16)
C7	0.6099 (5)	0.3340 (5)	0.6655 (3)	0.0483 (17)
H7A	0.5309	0.3315	0.6337	0.058*
C8	0.7002 (7)	0.2476 (6)	0.6681 (3)	0.0563 (19)
H8A	0.6839	0.1876	0.6387	0.068*
C9	0.8187 (6)	0.2489 (5)	0.7156 (3)	0.0473 (17)
C10	0.8421 (6)	0.3419 (6)	0.7559 (3)	0.059 (2)
H10A	0.9232	0.3460	0.7862	0.071*
C11	0.7479 (6)	0.4292 (6)	0.7522 (3)	0.0563 (19)
H11A	0.7665	0.4905	0.7806	0.068*
C12	0.4301 (6)	0.4650 (5)	0.7545 (3)	0.0461 (16)
C13	0.4486 (6)	0.4907 (6)	0.8175 (3)	0.062 (2)
H13A	0.5143	0.5455	0.8340	0.075*
C14	0.3732 (6)	0.4388 (6)	0.8595 (3)	0.062 (2)
H14A	0.3908	0.4564	0.9029	0.075*
C15	0.2737 (7)	0.3620 (6)	0.8339 (3)	0.0552 (19)
C16	0.2504 (6)	0.3338 (5)	0.7715 (3)	0.0543 (18)
H16A	0.1823	0.2810	0.7550	0.065*
C17	0.3289 (6)	0.3840 (5)	0.7315 (3)	0.0494 (17)
H17A	0.3135	0.3631	0.6886	0.059*
C18	0.3496 (7)	0.8259 (6)	0.5292 (3)	0.0500 (17)
C19	0.2533 (6)	0.9125 (5)	0.5439 (3)	0.0452 (17)
H19A	0.1741	0.8893	0.5573	0.054*
C20	0.2785 (6)	1.0231 (6)	0.5384 (3)	0.0491 (17)
H20A	0.3574	1.0400	0.5231	0.059*
C21	0.2005 (6)	1.1230 (6)	0.5527 (3)	0.0466 (16)
C22	0.2556 (6)	1.2308 (6)	0.5522 (3)	0.0543 (18)
H22A	0.3449	1.2390	0.5460	0.065*
C23	0.1802 (7)	1.3288 (6)	0.5610 (3)	0.061 (2)
H23A	0.2167	1.4020	0.5588	0.074*
C24	0.0504 (7)	1.3141 (6)	0.5729 (3)	0.0522 (18)
C25	−0.0090 (7)	1.2091 (6)	0.5737 (3)	0.0583 (19)
H25A	−0.0983	1.2011	0.5800	0.070*
C26	0.0699 (6)	1.1140 (6)	0.5648 (3)	0.0586 (19)
H26A	0.0329	1.0411	0.5671	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O	0.067 (3)	0.065 (3)	0.043 (3)	−0.005 (2)	0.024 (2)	0.008 (2)
Br1	0.0670 (5)	0.0714 (5)	0.0907 (7)	0.0136 (4)	0.0157 (4)	0.0143 (5)
N1	0.065 (4)	0.053 (4)	0.060 (4)	0.011 (3)	0.019 (3)	0.011 (3)
C1	0.061 (5)	0.067 (5)	0.052 (5)	0.016 (4)	0.017 (4)	0.003 (4)
Br2	0.0751 (6)	0.1359 (8)	0.0414 (5)	0.0163 (6)	0.0169 (4)	0.0266 (5)
N2	0.051 (3)	0.052 (3)	0.028 (3)	0.008 (3)	0.004 (2)	0.007 (3)
C2	0.063 (4)	0.061 (4)	0.048 (5)	−0.004 (4)	0.019 (4)	0.007 (4)
Br3	0.0988 (7)	0.0678 (5)	0.0948 (7)	0.0127 (5)	0.0369 (5)	−0.0054 (5)
C3	0.049 (4)	0.060 (5)	0.059 (5)	0.003 (4)	0.014 (4)	0.021 (4)
C4	0.059 (4)	0.051 (4)	0.063 (5)	0.008 (4)	0.030 (4)	0.016 (4)
C5	0.044 (4)	0.059 (4)	0.049 (5)	0.001 (3)	0.004 (3)	−0.012 (4)
C6	0.054 (4)	0.048 (4)	0.035 (4)	−0.012 (4)	0.008 (3)	0.002 (4)
C7	0.025 (3)	0.065 (5)	0.050 (4)	−0.011 (3)	−0.005 (3)	−0.001 (4)
C8	0.063 (5)	0.054 (5)	0.052 (5)	−0.005 (4)	0.012 (4)	−0.007 (4)
C9	0.044 (4)	0.043 (4)	0.055 (5)	0.001 (3)	0.011 (4)	0.014 (4)
C10	0.035 (4)	0.070 (5)	0.073 (6)	−0.010 (4)	0.015 (4)	0.007 (4)
C11	0.043 (4)	0.070 (5)	0.053 (5)	0.008 (4)	0.002 (3)	−0.011 (4)
C12	0.048 (4)	0.046 (4)	0.042 (5)	0.004 (3)	0.003 (3)	−0.007 (3)
C13	0.062 (5)	0.075 (5)	0.042 (5)	0.017 (4)	−0.009 (4)	−0.008 (4)
C14	0.055 (5)	0.096 (6)	0.033 (5)	0.017 (4)	−0.001 (4)	0.006 (4)
C15	0.065 (5)	0.083 (5)	0.022 (4)	0.016 (4)	0.019 (3)	0.007 (4)
C16	0.057 (4)	0.064 (5)	0.042 (4)	0.000 (4)	0.010 (3)	−0.009 (4)
C17	0.052 (4)	0.071 (4)	0.026 (4)	−0.003 (4)	0.011 (3)	0.008 (4)
C18	0.060 (4)	0.056 (4)	0.034 (4)	0.004 (4)	0.009 (3)	0.017 (4)
C19	0.040 (3)	0.063 (5)	0.032 (4)	0.005 (4)	0.005 (3)	0.013 (3)
C20	0.050 (4)	0.062 (5)	0.033 (4)	−0.013 (4)	0.000 (3)	0.016 (4)
C21	0.065 (4)	0.056 (4)	0.019 (4)	0.000 (4)	0.009 (3)	−0.001 (3)
C22	0.049 (4)	0.068 (5)	0.039 (4)	−0.013 (4)	−0.007 (3)	−0.006 (4)
C23	0.068 (5)	0.064 (5)	0.051 (5)	0.009 (4)	0.009 (4)	0.005 (4)
C24	0.074 (5)	0.050 (4)	0.026 (4)	0.005 (4)	−0.007 (3)	−0.011 (3)
C25	0.062 (5)	0.069 (5)	0.045 (4)	0.002 (4)	0.012 (3)	−0.008 (4)
C26	0.053 (4)	0.057 (5)	0.071 (5)	−0.003 (4)	0.022 (4)	0.015 (4)

Geometric parameters (Å, º) top

O—C18	1.216 (6)	C9—C10	1.372 (8)
Br1—C9	1.887 (6)	C10—C11	1.373 (7)
N1—C18	1.368 (7)	C10—H10A	0.9300
N1—C2	1.444 (7)	C11—H11A	0.9300
N1—C3	1.466 (6)	C12—C13	1.351 (7)
C1—N2	1.467 (6)	C12—C17	1.394 (7)
C1—C2	1.498 (7)	C13—C14	1.413 (6)
C1—H1A	0.9700	C13—H13A	0.9300
C1—H1B	0.9700	C14—C15	1.365 (8)
Br2—C15	1.897 (6)	C14—H14A	0.9300
N2—C4	1.445 (6)	C15—C16	1.344 (8)
N2—C5	1.460 (7)	C16—C17	1.393 (7)
C2—H2A	0.9700	C16—H16A	0.9300
C2—H2B	0.9700	C17—H17A	0.9300
Br3—C24	1.902 (6)	C18—C19	1.466 (7)
C3—C4	1.524 (7)	C19—C20	1.320 (7)
C3—H3A	0.9700	C19—H19A	0.9300
C3—H3B	0.9700	C20—C21	1.462 (8)
C4—H4A	0.9700	C20—H20A	0.9300
C4—H4B	0.9700	C21—C22	1.368 (8)
C5—C6	1.488 (7)	C21—C26	1.379 (7)
C5—C12	1.520 (7)	C22—C23	1.396 (7)
C5—H5A	0.9800	C22—H22A	0.9300
C6—C11	1.367 (7)	C23—C24	1.377 (7)
C6—C7	1.417 (6)	C23—H23A	0.9300
C7—C8	1.341 (7)	C24—C25	1.358 (7)
C7—H7A	0.9300	C25—C26	1.390 (7)
C8—C9	1.394 (8)	C25—H25A	0.9300
C8—H8A	0.9300	C26—H26A	0.9300

C18—N1—C2	120.2 (5)	C11—C10—H10A	119.4
C18—N1—C3	125.1 (6)	C6—C11—C10	122.1 (7)
C2—N1—C3	113.4 (5)	C6—C11—H11A	119.0
N2—C1—C2	111.6 (5)	C10—C11—H11A	119.0
N2—C1—H1A	109.3	C13—C12—C17	116.4 (6)
C2—C1—H1A	109.3	C13—C12—C5	122.8 (6)
N2—C1—H1B	109.3	C17—C12—C5	120.7 (6)
C2—C1—H1B	109.3	C12—C13—C14	123.4 (7)
H1A—C1—H1B	108.0	C12—C13—H13A	118.3
C4—N2—C5	110.0 (5)	C14—C13—H13A	118.3
C4—N2—C1	108.3 (5)	C15—C14—C13	117.4 (6)
C5—N2—C1	111.8 (5)	C15—C14—H14A	121.3
N1—C2—C1	111.5 (5)	C13—C14—H14A	121.3
N1—C2—H2A	109.3	C16—C15—C14	121.6 (6)
C1—C2—H2A	109.3	C16—C15—Br2	120.6 (6)
N1—C2—H2B	109.3	C14—C15—Br2	117.8 (5)
C1—C2—H2B	109.3	C15—C16—C17	119.7 (6)
H2A—C2—H2B	108.0	C15—C16—H16A	120.2
N1—C3—C4	109.3 (5)	C17—C16—H16A	120.2
N1—C3—H3A	109.8	C16—C17—C12	121.4 (6)
C4—C3—H3A	109.8	C16—C17—H17A	119.3
N1—C3—H3B	109.8	C12—C17—H17A	119.3
C4—C3—H3B	109.8	O—C18—N1	119.5 (6)
H3A—C3—H3B	108.3	O—C18—C19	122.3 (6)
N2—C4—C3	114.2 (5)	N1—C18—C19	117.9 (6)
N2—C4—H4A	108.7	C20—C19—C18	120.4 (6)
C3—C4—H4A	108.7	C20—C19—H19A	119.8
N2—C4—H4B	108.7	C18—C19—H19A	119.8
C3—C4—H4B	108.7	C19—C20—C21	129.6 (6)
H4A—C4—H4B	107.6	C19—C20—H20A	115.2
N2—C5—C6	115.4 (5)	C21—C20—H20A	115.2
N2—C5—C12	111.6 (5)	C22—C21—C26	117.7 (6)
C6—C5—C12	106.4 (5)	C22—C21—C20	119.7 (6)
N2—C5—H5A	107.7	C26—C21—C20	122.5 (6)
C6—C5—H5A	107.7	C21—C22—C23	121.3 (6)
C12—C5—H5A	107.7	C21—C22—H22A	119.4
C11—C6—C7	115.2 (6)	C23—C22—H22A	119.4
C11—C6—C5	121.1 (6)	C24—C23—C22	118.2 (6)
C7—C6—C5	123.4 (6)	C24—C23—H23A	120.9
C8—C7—C6	123.9 (6)	C22—C23—H23A	120.9
C8—C7—H7A	118.1	C25—C24—C23	122.7 (6)
C6—C7—H7A	118.1	C25—C24—Br3	118.4 (6)
C7—C8—C9	119.1 (6)	C23—C24—Br3	118.8 (5)
C7—C8—H8A	120.4	C24—C25—C26	117.0 (6)
C9—C8—H8A	120.4	C24—C25—H25A	121.5
C10—C9—C8	118.5 (6)	C26—C25—H25A	121.5
C10—C9—Br1	120.9 (5)	C21—C26—C25	123.0 (6)
C8—C9—Br1	120.6 (5)	C21—C26—H26A	118.5
C9—C10—C11	121.2 (6)	C25—C26—H26A	118.5
C9—C10—H10A	119.4

C2—C1—N2—C4	−57.4 (7)	C6—C5—C12—C17	−80.8 (7)
C2—C1—N2—C5	−178.7 (5)	C17—C12—C13—C14	1.1 (10)
C18—N1—C2—C1	114.1 (6)	C5—C12—C13—C14	−175.5 (6)
C3—N1—C2—C1	−53.7 (7)	C12—C13—C14—C15	−2.4 (10)
N2—C1—C2—N1	56.8 (7)	C13—C14—C15—C16	1.9 (10)
C18—N1—C3—C4	−116.3 (7)	C13—C14—C15—Br2	−177.7 (5)
C2—N1—C3—C4	50.7 (7)	C14—C15—C16—C17	−0.2 (10)
C5—N2—C4—C3	179.4 (5)	Br2—C15—C16—C17	179.4 (5)
C1—N2—C4—C3	57.0 (7)	C15—C16—C17—C12	−1.2 (10)
N1—C3—C4—N2	−53.7 (7)	C13—C12—C17—C16	0.7 (9)
C4—N2—C5—C6	−176.0 (5)	C5—C12—C17—C16	177.4 (6)
C1—N2—C5—C6	−55.7 (7)	C2—N1—C18—O	11.9 (10)
C4—N2—C5—C12	62.3 (6)	C3—N1—C18—O	178.2 (6)
C1—N2—C5—C12	−177.3 (5)	C2—N1—C18—C19	−174.8 (5)
N2—C5—C6—C11	147.7 (6)	C3—N1—C18—C19	−8.5 (10)
C12—C5—C6—C11	−87.9 (7)	O—C18—C19—C20	−23.9 (10)
N2—C5—C6—C7	−39.8 (8)	N1—C18—C19—C20	162.9 (6)
C12—C5—C6—C7	84.6 (7)	C18—C19—C20—C21	−177.4 (6)
C11—C6—C7—C8	2.1 (9)	C19—C20—C21—C22	170.6 (6)
C5—C6—C7—C8	−170.8 (6)	C19—C20—C21—C26	−11.8 (10)
C6—C7—C8—C9	0.6 (10)	C26—C21—C22—C23	−2.6 (9)
C7—C8—C9—C10	−3.4 (9)	C20—C21—C22—C23	175.2 (6)
C7—C8—C9—Br1	173.4 (4)	C21—C22—C23—C24	2.7 (9)
C8—C9—C10—C11	3.6 (9)	C22—C23—C24—C25	−2.9 (10)
Br1—C9—C10—C11	−173.2 (5)	C22—C23—C24—Br3	178.4 (5)
C7—C6—C11—C10	−1.9 (9)	C23—C24—C25—C26	2.9 (10)
C5—C6—C11—C10	171.2 (5)	Br3—C24—C25—C26	−178.4 (5)
C9—C10—C11—C6	−0.9 (10)	C22—C21—C26—C25	2.7 (10)
N2—C5—C12—C13	−137.7 (6)	C20—C21—C26—C25	−175.0 (6)
C6—C5—C12—C13	95.7 (7)	C24—C25—C26—C21	−2.8 (10)
N2—C5—C12—C17	45.9 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20A···Oⁱ	0.93	2.60	3.480 (7)	159
C2—H2A···O	0.97	2.28	2.710 (7)	106
C20—H20A···O	0.93	2.49	2.821 (8)	101

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₃Br₃N₂O
M_r	619.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.956 (2), 11.624 (2), 21.310 (4)
β (°)	101.45 (3)
V (Å³)	2417.1 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.03
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.433, 0.633
No. of measured, independent and observed [I > 2σ(I)] reflections	4701, 4432, 2081
R_int	0.098
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.082, 1.01
No. of reflections	4432
No. of parameters	289
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.42

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20A···Oⁱ	0.93	2.60	3.480 (7)	159

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

The authors thank Professor Hua-Qin Wang of the Analysis Centre, Nanjing University, for the diffraction measurements. This work was supported by the Natural Science Foundation of the Education Department of Jiangsu Province (No. 05KJB350084) and the Natural Science Foundation of Jiangsu Province (No. BK2010538).

References

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Qian, Y., Zhang, H.-J., Zhang, H., Xu, J. & Zhu, H.-L. (2010). Bioorg. Med. Chem. 18, 4991–4996. Web of Science CSD CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, Y., Chen, Q.-X., Wang, Q., Song, K.-K. & Qiu, L. (2005). Food Chem. 92, 707–712. CrossRef CAS Google Scholar
Teng, Y.-B., Dai, Z.-H. & Wu, B. (2011). Acta Cryst. E67, o697. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wu, B., Zhou, L. & Cai, H.-H. (2008). Chin. Chem. Lett. 19, 1163–1166. Web of Science CrossRef CAS Google Scholar

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(E)-1-{4-[Bis(4-bromo­phen­yl)meth­yl]piperazin-1-yl}-3-(4-bromo­phen­yl)prop-2-en-1-one

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organic compounds

(E)-1-{4-[Bis(4-bromophenyl)methyl]piperazin-1-yl}-3-(4-bromophenyl)prop-2-en-1-one