(E)-1-{4-[Bis(4-bromo-phen-yl)meth-yl]piperazin-1-yl}-3-(4-bromo-phen-yl)prop-2-en-1-one.

In the title mol-ecule, C(26)H(23)Br(3)N(2)O, the piperazine ring adopts a chair conformation and the C=C double bond has an E configuration. In the crystal, mol-ecules are linked through weak inter-molecular 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 = 619.19

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.082

S = 1.01

4432 reflections

289 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.42 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811048380/pv2478sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048380/pv2478Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048380/pv2478Isup3.cml

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

C26H23Br3N2O	F(000) = 1224
Mr = 619.19	Dx = 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

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

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(Fo2) + (0.0185P)2] where P = (Fo2 + 2Fc2)/3
4432 reflections	(Δ/σ)max = 0.001
289 parameters	Δρmax = 0.35 e Å−3
2 restraints	Δρmin = −0.42 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
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*

	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)

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)

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

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) .