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

In the title compound, C(28)H(28)Br(2)N(2)O(2), the C=C double bond has an E configuration and the piperazine ring has a chair conformation, with the N-C bonds in equatorial orientations. The dihedral angle between the bromo-benzene rings is 83.1 (4)°. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯Br hydrogen bonds.

Related literature

For related structures and background to cinnamic acid derivatives, see: Teng et al. (2011 ▶); Zhong et al. (2012 ▶). For further synthetic details, see: Wu et al. (2008 ▶).

Experimental

Crystal data

C28H28Br2N2O2

M = 584.34

Triclinic,

a = 10.423 (2) Å

b = 10.903 (2) Å

c = 12.824 (3) Å

α = 74.29 (3)°

β = 73.56 (3)°

γ = 71.59 (3)°

V = 1299.6 (5) Å3

Z = 2

Mo Kα radiation

μ = 3.15 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 = 0.572, T max = 0.744

5064 measured reflections

4778 independent reflections

2268 reflections with I > 2σ(I)

R int = 0.069

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.157

S = 1.00

4778 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.62 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ▶); cell refinement: XCAD4 (Harms & Wocadlo, 1995 ▶); data reduction: XCAD4; 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/S1600536812003819/hb6615sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003819/hb6615Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812003819/hb6615Isup3.cml

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

C28H28Br2N2O2	Z = 2
Mr = 584.34	F(000) = 592
Triclinic, P1	Dx = 1.493 Mg m−3
a = 10.423 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.903 (2) Å	Cell parameters from 25 reflections
c = 12.824 (3) Å	θ = 9–12°
α = 74.29 (3)°	µ = 3.15 mm−1
β = 73.56 (3)°	T = 293 K
γ = 71.59 (3)°	Block, colorless
V = 1299.6 (5) Å3	0.20 × 0.10 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	2268 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.069
Graphite monochromator	θmax = 25.4°, θmin = 1.7°
ω/2θ scans	h = 0→12
Absorption correction: ψ scan (North et al., 1968)	k = −12→13
Tmin = 0.572, Tmax = 0.744	l = −14→15
5064 measured reflections	3 standard reflections every 200 reflections
4778 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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.063P)2] where P = (Fo2 + 2Fc2)/3
4778 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.62 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
Br1	−0.31209 (9)	0.97529 (9)	0.41018 (8)	0.0772 (4)
N1	0.4018 (6)	0.7583 (6)	0.2995 (4)	0.0444 (15)
O1	0.8264 (5)	0.5375 (5)	0.4350 (4)	0.0636 (15)
C1	0.3172 (7)	0.8540 (7)	0.2261 (5)	0.0409 (17)
H1A	0.3478	0.9354	0.2026	0.049*
Br2	0.33465 (8)	0.64618 (9)	−0.18076 (7)	0.0655 (3)
O2	0.8295 (5)	0.7395 (5)	1.0157 (4)	0.0644 (16)
N2	0.6065 (6)	0.6446 (5)	0.4291 (4)	0.0471 (15)
C2	0.1658 (7)	0.8848 (7)	0.2841 (5)	0.0395 (17)
C3	0.1050 (7)	0.7871 (7)	0.3459 (6)	0.0499 (19)
H3A	0.1594	0.7011	0.3601	0.060*
C4	−0.0386 (8)	0.8139 (8)	0.3888 (6)	0.058 (2)
H4A	−0.0797	0.7472	0.4321	0.069*
C5	−0.1149 (7)	0.9390 (8)	0.3653 (6)	0.052 (2)
C6	−0.0569 (8)	1.0417 (8)	0.3059 (7)	0.070 (3)
H6A	−0.1109	1.1281	0.2927	0.084*
C7	0.0832 (7)	1.0110 (7)	0.2674 (6)	0.060 (2)
H7A	0.1246	1.0789	0.2280	0.072*
C8	0.3295 (6)	0.8018 (7)	0.1241 (6)	0.0378 (17)
C9	0.3366 (7)	0.6702 (7)	0.1330 (6)	0.0488 (19)
H9A	0.3403	0.6124	0.2010	0.059*
C10	0.3382 (7)	0.6244 (7)	0.0428 (6)	0.0464 (18)
H10A	0.3439	0.5359	0.0492	0.056*
C11	0.3315 (7)	0.7093 (8)	−0.0554 (6)	0.0463 (19)
C12	0.3232 (7)	0.8403 (8)	−0.0682 (6)	0.052 (2)
H12A	0.3177	0.8977	−0.1362	0.063*
C13	0.3234 (7)	0.8846 (7)	0.0228 (6)	0.0473 (19)
H13A	0.3193	0.9729	0.0153	0.057*
C14	0.5494 (7)	0.7223 (7)	0.2480 (6)	0.051 (2)
H14A	0.5864	0.7983	0.2320	0.062*
H14B	0.5613	0.6967	0.1784	0.062*
C15	0.6267 (7)	0.6126 (7)	0.3213 (5)	0.050 (2)
H15A	0.5958	0.5342	0.3315	0.060*
H15B	0.7246	0.5936	0.2867	0.060*
C16	0.4626 (7)	0.6980 (8)	0.4790 (6)	0.053 (2)
H16A	0.4580	0.7315	0.5431	0.064*
H16B	0.4153	0.6281	0.5043	0.064*
C17	0.3915 (7)	0.8055 (7)	0.3996 (6)	0.051 (2)
H17A	0.2948	0.8364	0.4344	0.061*
H17B	0.4334	0.8788	0.3791	0.061*
C18	0.7144 (8)	0.5993 (7)	0.4799 (6)	0.0458 (18)
C19	0.6976 (7)	0.6322 (7)	0.5881 (6)	0.0487 (19)
H19A	0.6105	0.6753	0.6236	0.058*
C20	0.8030 (7)	0.6019 (7)	0.6349 (5)	0.0441 (18)
H20A	0.8859	0.5529	0.5984	0.053*
C21	0.8080 (7)	0.6342 (7)	0.7358 (5)	0.0402 (17)
C22	0.9325 (7)	0.6010 (7)	0.7672 (6)	0.0506 (19)
H22A	1.0115	0.5553	0.7240	0.061*
C23	0.9439 (7)	0.6326 (7)	0.8587 (6)	0.051 (2)
H23A	1.0299	0.6093	0.8770	0.062*
C24	0.8290 (7)	0.6989 (7)	0.9245 (6)	0.0450 (18)
C25	0.7031 (7)	0.7326 (7)	0.8959 (6)	0.049 (2)
H25A	0.6238	0.7761	0.9403	0.059*
C26	0.6947 (7)	0.7022 (7)	0.8028 (6)	0.0491 (19)
H26A	0.6092	0.7283	0.7833	0.059*
C27	0.9597 (8)	0.7367 (8)	1.0333 (6)	0.063 (2)
H27A	1.0113	0.7814	0.9664	0.075*
H27B	1.0134	0.6460	1.0502	0.075*
C28	0.9381 (10)	0.8017 (10)	1.1251 (8)	0.106 (4)
H28A	1.0262	0.7982	1.1370	0.159*
H28B	0.8869	0.7574	1.1912	0.159*
H28C	0.8871	0.8921	1.1073	0.159*

	U11	U22	U33	U12	U13	U23
Br1	0.0486 (5)	0.0800 (7)	0.0987 (8)	−0.0114 (5)	0.0050 (5)	−0.0390 (6)
N1	0.044 (4)	0.055 (4)	0.036 (3)	−0.006 (3)	−0.008 (3)	−0.021 (3)
O1	0.050 (3)	0.087 (4)	0.057 (3)	0.001 (3)	−0.016 (3)	−0.036 (3)
C1	0.045 (4)	0.043 (5)	0.036 (4)	−0.014 (4)	−0.008 (4)	−0.008 (3)
Br2	0.0573 (6)	0.0891 (7)	0.0612 (6)	−0.0102 (5)	−0.0137 (4)	−0.0422 (5)
O2	0.045 (3)	0.101 (4)	0.062 (3)	−0.014 (3)	−0.012 (3)	−0.046 (3)
N2	0.043 (4)	0.052 (4)	0.045 (4)	0.002 (3)	−0.010 (3)	−0.023 (3)
C2	0.042 (4)	0.035 (4)	0.038 (4)	−0.007 (4)	−0.014 (3)	0.000 (3)
C3	0.047 (5)	0.033 (4)	0.064 (5)	−0.004 (4)	−0.012 (4)	−0.008 (4)
C4	0.054 (5)	0.051 (5)	0.063 (5)	−0.012 (4)	−0.005 (4)	−0.015 (4)
C5	0.040 (4)	0.057 (5)	0.064 (5)	0.001 (4)	−0.013 (4)	−0.033 (4)
C6	0.050 (5)	0.043 (5)	0.103 (7)	−0.003 (4)	0.002 (5)	−0.024 (5)
C7	0.043 (5)	0.043 (5)	0.082 (6)	−0.008 (4)	−0.005 (4)	−0.005 (4)
C8	0.032 (4)	0.042 (5)	0.040 (4)	−0.007 (3)	−0.011 (3)	−0.009 (4)
C9	0.058 (5)	0.053 (5)	0.040 (4)	−0.020 (4)	−0.014 (4)	−0.007 (4)
C10	0.055 (5)	0.036 (4)	0.049 (5)	−0.010 (4)	−0.014 (4)	−0.009 (4)
C11	0.032 (4)	0.056 (5)	0.056 (5)	−0.003 (4)	−0.008 (4)	−0.030 (4)
C12	0.052 (5)	0.067 (6)	0.035 (4)	−0.008 (4)	−0.013 (4)	−0.013 (4)
C13	0.054 (5)	0.036 (4)	0.047 (5)	−0.005 (4)	−0.013 (4)	−0.006 (4)
C14	0.042 (4)	0.064 (5)	0.048 (5)	−0.003 (4)	−0.003 (4)	−0.030 (4)
C15	0.058 (5)	0.057 (5)	0.037 (4)	−0.001 (4)	−0.017 (4)	−0.023 (4)
C16	0.044 (5)	0.074 (6)	0.043 (5)	−0.007 (4)	−0.004 (4)	−0.029 (4)
C17	0.039 (4)	0.067 (6)	0.050 (5)	−0.005 (4)	−0.007 (4)	−0.030 (4)
C18	0.047 (5)	0.051 (5)	0.040 (4)	−0.009 (4)	−0.012 (4)	−0.013 (4)
C19	0.041 (4)	0.060 (5)	0.050 (5)	−0.009 (4)	−0.011 (4)	−0.023 (4)
C20	0.041 (4)	0.045 (5)	0.044 (4)	0.001 (4)	−0.017 (4)	−0.012 (4)
C21	0.034 (4)	0.052 (5)	0.037 (4)	−0.013 (4)	−0.009 (3)	−0.010 (3)
C22	0.046 (5)	0.056 (5)	0.048 (5)	−0.006 (4)	−0.009 (4)	−0.018 (4)
C23	0.037 (4)	0.068 (6)	0.057 (5)	−0.008 (4)	−0.011 (4)	−0.031 (4)
C24	0.045 (5)	0.052 (5)	0.046 (4)	−0.021 (4)	−0.010 (4)	−0.011 (4)
C25	0.036 (4)	0.067 (6)	0.055 (5)	−0.016 (4)	−0.005 (4)	−0.030 (4)
C26	0.039 (4)	0.062 (5)	0.055 (5)	−0.014 (4)	−0.013 (4)	−0.023 (4)
C27	0.057 (5)	0.078 (6)	0.063 (6)	−0.013 (5)	−0.029 (4)	−0.017 (5)
C28	0.093 (7)	0.147 (10)	0.113 (8)	−0.015 (7)	−0.041 (6)	−0.081 (8)

Br1—C5	1.911 (7)	C13—H13A	0.9300
N1—C1	1.452 (8)	C14—C15	1.475 (9)
N1—C14	1.463 (8)	C14—H14A	0.9700
N1—C17	1.473 (8)	C14—H14B	0.9700
O1—C18	1.217 (8)	C15—H15A	0.9700
C1—C2	1.514 (9)	C15—H15B	0.9700
C1—C8	1.520 (9)	C16—C17	1.480 (9)
C1—H1A	0.9800	C16—H16A	0.9700
Br2—C11	1.901 (7)	C16—H16B	0.9700
O2—C24	1.360 (7)	C17—H17A	0.9700
O2—C27	1.428 (8)	C17—H17B	0.9700
N2—C18	1.350 (8)	C18—C19	1.476 (9)
N2—C16	1.451 (8)	C19—C20	1.309 (8)
N2—C15	1.458 (7)	C19—H19A	0.9300
C2—C3	1.360 (9)	C20—C21	1.448 (9)
C2—C7	1.370 (9)	C20—H20A	0.9300
C3—C4	1.404 (9)	C21—C22	1.378 (9)
C3—H3A	0.9300	C21—C26	1.379 (9)
C4—C5	1.346 (10)	C22—C23	1.355 (9)
C4—H4A	0.9300	C22—H22A	0.9300
C5—C6	1.380 (10)	C23—C24	1.371 (9)
C6—C7	1.364 (9)	C23—H23A	0.9300
C6—H6A	0.9300	C24—C25	1.375 (9)
C7—H7A	0.9300	C25—C26	1.354 (8)
C8—C13	1.372 (9)	C25—H25A	0.9300
C8—C9	1.388 (9)	C26—H26A	0.9300
C9—C10	1.373 (9)	C27—C28	1.462 (10)
C9—H9A	0.9300	C27—H27A	0.9700
C10—C11	1.351 (9)	C27—H27B	0.9700
C10—H10A	0.9300	C28—H28A	0.9600
C11—C12	1.371 (10)	C28—H28B	0.9600
C12—C13	1.379 (9)	C28—H28C	0.9600
C12—H12A	0.9300
C1—N1—C14	113.9 (5)	N2—C15—H15A	109.4
C1—N1—C17	112.4 (5)	C14—C15—H15A	109.4
C14—N1—C17	106.2 (5)	N2—C15—H15B	109.4
N1—C1—C2	111.0 (5)	C14—C15—H15B	109.4
N1—C1—C8	111.0 (5)	H15A—C15—H15B	108.0
C2—C1—C8	107.5 (5)	N2—C16—C17	111.6 (6)
N1—C1—H1A	109.1	N2—C16—H16A	109.3
C2—C1—H1A	109.1	C17—C16—H16A	109.3
C8—C1—H1A	109.1	N2—C16—H16B	109.3
C24—O2—C27	118.1 (5)	C17—C16—H16B	109.3
C18—N2—C16	126.7 (6)	H16A—C16—H16B	108.0
C18—N2—C15	118.0 (5)	N1—C17—C16	110.3 (6)
C16—N2—C15	113.8 (5)	N1—C17—H17A	109.6
C3—C2—C7	118.0 (7)	C16—C17—H17A	109.6
C3—C2—C1	121.2 (6)	N1—C17—H17B	109.6
C7—C2—C1	120.6 (6)	C16—C17—H17B	109.6
C2—C3—C4	121.2 (7)	H17A—C17—H17B	108.1
C2—C3—H3A	119.4	O1—C18—N2	120.7 (6)
C4—C3—H3A	119.4	O1—C18—C19	120.0 (7)
C5—C4—C3	118.0 (7)	N2—C18—C19	119.2 (6)
C5—C4—H4A	121.0	C20—C19—C18	121.2 (7)
C3—C4—H4A	121.0	C20—C19—H19A	119.4
C4—C5—C6	122.6 (7)	C18—C19—H19A	119.4
C4—C5—Br1	118.9 (6)	C19—C20—C21	128.8 (7)
C6—C5—Br1	118.4 (6)	C19—C20—H20A	115.6
C7—C6—C5	117.1 (7)	C21—C20—H20A	115.6
C7—C6—H6A	121.5	C22—C21—C26	116.2 (6)
C5—C6—H6A	121.5	C22—C21—C20	119.8 (6)
C6—C7—C2	123.0 (7)	C26—C21—C20	123.9 (6)
C6—C7—H7A	118.5	C23—C22—C21	122.3 (7)
C2—C7—H7A	118.5	C23—C22—H22A	118.8
C13—C8—C9	118.0 (6)	C21—C22—H22A	118.8
C13—C8—C1	121.3 (6)	C22—C23—C24	120.1 (7)
C9—C8—C1	120.5 (6)	C22—C23—H23A	119.9
C10—C9—C8	120.9 (7)	C24—C23—H23A	119.9
C10—C9—H9A	119.6	O2—C24—C23	125.0 (6)
C8—C9—H9A	119.6	O2—C24—C25	116.0 (6)
C11—C10—C9	119.3 (7)	C23—C24—C25	119.0 (6)
C11—C10—H10A	120.4	C26—C25—C24	119.9 (7)
C9—C10—H10A	120.4	C26—C25—H25A	120.1
C10—C11—C12	122.1 (7)	C24—C25—H25A	120.1
C10—C11—Br2	119.4 (6)	C25—C26—C21	122.5 (7)
C12—C11—Br2	118.5 (6)	C25—C26—H26A	118.7
C11—C12—C13	118.0 (7)	C21—C26—H26A	118.7
C11—C12—H12A	121.0	O2—C27—C28	110.1 (7)
C13—C12—H12A	121.0	O2—C27—H27A	109.7
C8—C13—C12	121.8 (7)	C28—C27—H27A	109.7
C8—C13—H13A	119.1	O2—C27—H27B	109.6
C12—C13—H13A	119.1	C28—C27—H27B	109.7
N1—C14—C15	111.2 (6)	H27A—C27—H27B	108.2
N1—C14—H14A	109.4	C27—C28—H28A	109.5
C15—C14—H14A	109.4	C27—C28—H28B	109.5
N1—C14—H14B	109.4	H28A—C28—H28B	109.5
C15—C14—H14B	109.4	C27—C28—H28C	109.5
H14A—C14—H14B	108.0	H28A—C28—H28C	109.5
N2—C15—C14	111.3 (5)	H28B—C28—H28C	109.5
C14—N1—C1—C2	179.1 (5)	C1—N1—C14—C15	−172.4 (5)
C17—N1—C1—C2	−60.1 (7)	C17—N1—C14—C15	63.3 (7)
C14—N1—C1—C8	59.5 (7)	C18—N2—C15—C14	−144.3 (7)
C17—N1—C1—C8	−179.7 (5)	C16—N2—C15—C14	48.3 (8)
N1—C1—C2—C3	−45.3 (8)	N1—C14—C15—N2	−56.4 (8)
C8—C1—C2—C3	76.4 (8)	C18—N2—C16—C17	145.1 (7)
N1—C1—C2—C7	140.7 (7)	C15—N2—C16—C17	−48.8 (8)
C8—C1—C2—C7	−97.7 (8)	C1—N1—C17—C16	171.7 (6)
C7—C2—C3—C4	1.8 (11)	C14—N1—C17—C16	−63.1 (7)
C1—C2—C3—C4	−172.4 (6)	N2—C16—C17—N1	56.8 (8)
C2—C3—C4—C5	1.1 (11)	C16—N2—C18—O1	168.1 (7)
C3—C4—C5—C6	−3.2 (11)	C15—N2—C18—O1	2.5 (11)
C3—C4—C5—Br1	174.0 (5)	C16—N2—C18—C19	−15.5 (11)
C4—C5—C6—C7	2.3 (12)	C15—N2—C18—C19	178.9 (6)
Br1—C5—C6—C7	−174.9 (6)	O1—C18—C19—C20	3.4 (11)
C5—C6—C7—C2	0.9 (12)	N2—C18—C19—C20	−173.0 (7)
C3—C2—C7—C6	−2.8 (12)	C18—C19—C20—C21	175.2 (7)
C1—C2—C7—C6	171.4 (7)	C19—C20—C21—C22	−175.2 (8)
N1—C1—C8—C13	−146.2 (6)	C19—C20—C21—C26	2.2 (12)
C2—C1—C8—C13	92.2 (7)	C26—C21—C22—C23	0.2 (11)
N1—C1—C8—C9	38.8 (8)	C20—C21—C22—C23	177.8 (7)
C2—C1—C8—C9	−82.8 (8)	C21—C22—C23—C24	0.6 (12)
C13—C8—C9—C10	0.4 (10)	C27—O2—C24—C23	12.7 (11)
C1—C8—C9—C10	175.5 (6)	C27—O2—C24—C25	−164.7 (7)
C8—C9—C10—C11	−0.6 (11)	C22—C23—C24—O2	−177.5 (7)
C9—C10—C11—C12	0.1 (11)	C22—C23—C24—C25	−0.1 (11)
C9—C10—C11—Br2	179.7 (5)	O2—C24—C25—C26	176.4 (6)
C10—C11—C12—C13	0.7 (11)	C23—C24—C25—C26	−1.2 (11)
Br2—C11—C12—C13	−178.9 (5)	C24—C25—C26—C21	2.1 (12)
C9—C8—C13—C12	0.4 (10)	C22—C21—C26—C25	−1.6 (11)
C1—C8—C13—C12	−174.7 (6)	C20—C21—C26—C25	−179.1 (7)
C11—C12—C13—C8	−1.0 (10)	C24—O2—C27—C28	171.6 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···Br2i	0.97	2.91	3.605 (7)	129
C22—H22A···O1ii	0.93	2.47	3.370 (9)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯Br2i	0.97	2.91	3.605 (7)	129
C22—H22A⋯O1ii	0.93	2.47	3.370 (9)	161

Symmetry codes: (i) ; (ii) .