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

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

doi:10.1107/S1600536812003819

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o604

doi:10.1107/S1600536812003819

Open

access

(E)-1-{4-[Bis(4-bromophenyl)methyl]piperazin-1-yl}-3-(4-ethoxyphenyl)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 Animal, 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 27 January 2012; accepted 29 January 2012; online 4 February 2012)

In the title compound, C₂₈H₂₈Br₂N₂O₂, 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 bromobenzene rings is 83.1 (4)°. In the crystal, molecules 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_r = 584.34
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.068
wR(F²) = 0.157
S = 1.00
4778 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.62 e Å⁻³

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) -x+1, -y+1, -z; (ii) -x+2, -y+1, -z+1.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812003819/hb6615sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812003819/hb6615Isup3.cml

checkCIF report

Comment top

As a continuation of our study of cinnamic acid derivatives (Teng et al., 2011; Zhong et al., 2012), we present here the title compound (I). In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in related compounds (Teng et al., 2011; Zhong et al., 2012). The molecule of (I) exists an E configulation with respect to the C19=C20 ethene bond [1.309 (8)]. The piperazine ring adopts a chair conformation with puchering parameters Q = 0.566 (8), theta = 168.5 (7), phi = 178 (4). In the crystal, molecules are linked by C—H···O and C—H···Br hydrogen bonds.

Related literature top

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 top

The synthesis follows the method of Wu et al. (2008). The title compound was prepared by stirring a mixture of (E)-3-(4-ethoxyphenyl)acrylic acid (0.769 g; 4 mmol), thionyl chloride (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)iperazine (2.461 g; 6 mmol) in the presence of triethylamine (5 ml) for 12 h at room temperature. The resultant mixture was cooled. The solid, (E)-1-(4-(bis(4-bromophenyl)methyl)piperazin-1-yl)-3- (4-ethoxyphenyl)prop-2-en-1-one obtained was filtered and was recrystallized from ethanol. Colourless blocks were grown from an ethanol: acetonitrile:chloroform (1:1:1) solution by slow evaporation at room temperature.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989); cell refinement: XCAD4 (Harms & Wocadlo, 1995); 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 of (I) with displacement ellipsoids for non-H drawn at 70% probability level.
	Fig. 2. Packing diagram of the title compound.

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

Crystal data top

C₂₈H₂₈Br₂N₂O₂	Z = 2
M_r = 584.34	F(000) = 592
Triclinic, P1	D_x = 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

Data collection top

Enraf–Nonius CAD-4 diffractometer	2268 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.069
Graphite monochromator	θ_max = 25.4°, θ_min = 1.7°
ω/2θ scans	h = 0→12
Absorption correction: ψ scan (North et al., 1968)	k = −12→13
T_min = 0.572, T_max = 0.744	l = −14→15
5064 measured reflections	3 standard reflections every 200 reflections
4778 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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.063P)²] where P = (F_o² + 2F_c²)/3
4778 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.62 e Å⁻³

Crystal data top

C₂₈H₂₈Br₂N₂O₂	γ = 71.59 (3)°
M_r = 584.34	V = 1299.6 (5) Å³
Triclinic, P1	Z = 2
a = 10.423 (2) Å	Mo Kα radiation
b = 10.903 (2) Å	µ = 3.15 mm⁻¹
c = 12.824 (3) Å	T = 293 K
α = 74.29 (3)°	0.20 × 0.10 × 0.10 mm
β = 73.56 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2268 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.069
T_min = 0.572, T_max = 0.744	3 standard reflections every 200 reflections
5064 measured reflections	intensity decay: 1%
4778 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.157	H-atom parameters constrained
S = 1.00	Δρ_max = 0.57 e Å⁻³
4778 reflections	Δρ_min = −0.62 e Å⁻³
307 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z; (ii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₈Br₂N₂O₂
M_r	584.34
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.423 (2), 10.903 (2), 12.824 (3)
α, β, γ (°)	74.29 (3), 73.56 (3), 71.59 (3)
V (Å³)	1299.6 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.15
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.572, 0.744
No. of measured, independent and observed [I > 2σ(I)] reflections	5064, 4778, 2268
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.157, 1.00
No. of reflections	4778
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.62

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1989), 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
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) −x+1, −y+1, −z; (ii) −x+2, −y+1, −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 Jiangsu Province (grant No. BK2010538).

References

Enraf–Nonius (1989). 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
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals 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
Zhong, Y., Zhang, X. P. & Wu, B. (2012). Acta Cryst. E68, o122. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o604

doi:10.1107/S1600536812003819

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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