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

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

doi:10.1107/S1600536812003820

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o605

doi:10.1107/S1600536812003820

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(E)-1-{4-[Bis(4-bromophenyl)methyl]piperazin-1-yl}-3-(4-methylphenyl)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, C₂₇H₂₆Br₂N₂O, the piperazine ring adopts a chair conformation with the N—C bonds in equatorial orientations. The C=C double bond has an E configuration. The dihedral angle between the bromobenzene rings is 83.0 (4)°. In the crystal, inversion dimers linked through pairs of C—H⋯O hydrogen bonds generate R₂²(10) loops.

Related literature

For a related structure 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

C₂₇H₂₆Br₂N₂O
M_r = 554.32
Monoclinic, P 2₁ /c
a = 10.050 (2) Å
b = 11.622 (2) Å
c = 21.259 (4) Å
β = 101.72 (3)°
V = 2431.3 (8) Å³
Z = 4
Mo Kα radiation
μ = 3.36 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 = 0.553, T_max = 0.730
4720 measured reflections
4452 independent reflections
1998 reflections with I > 2σ(I)
R_int = 0.097
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.075
wR(F²) = 0.155
S = 1.00
4452 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.45 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	2.55	3.445 (10)	162
Symmetry code: (i) -x, -y-1, -z.

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/S1600536812003820/hb6616sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812003820/hb6616Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812003820/hb6616Isup3.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 [1.317 (10)]. The piperazine ring adopts a chair conformation with puchering parameters Q = 0.574 (8), Theta = 5.0 (7), Phi = 2(10). In the crystal, molecules are linked by C—H···O hydrogen bonds to form inversion dimers.

Related literature top

For a related structure 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-methylphenyl) acrylic acid (0.649 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-methylphenyl)prop-2-en-1-one obtained was filtered and was recrystallized from ethanol. Colourless blocks were grown from an ethanol:ethyl acetate (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-methylphenyl)prop-2-en-1-one top

Crystal data top

C₂₇H₂₆Br₂N₂O	F(000) = 1120
M_r = 554.32	D_x = 1.514 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.050 (2) Å	Cell parameters from 25 reflections
b = 11.622 (2) Å	θ = 9–13°
c = 21.259 (4) Å	µ = 3.36 mm⁻¹
β = 101.72 (3)°	T = 293 K
V = 2431.3 (8) Å³	Block, colorless
Z = 4	0.20 × 0.10 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1998 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.097
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 = 0.553, T_max = 0.730	l = −25→25
4720 measured reflections	3 standard reflections every 200 reflections
4452 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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.058P)²] where P = (F_o² + 2F_c²)/3
4452 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₂₇H₂₆Br₂N₂O	V = 2431.3 (8) Å³
M_r = 554.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.050 (2) Å	µ = 3.36 mm⁻¹
b = 11.622 (2) Å	T = 293 K
c = 21.259 (4) Å	0.20 × 0.10 × 0.10 mm
β = 101.72 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1998 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.097
T_min = 0.553, T_max = 0.730	3 standard reflections every 200 reflections
4720 measured reflections	intensity decay: 1%
4452 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	0 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 1.00	Δρ_max = 0.34 e Å⁻³
4452 reflections	Δρ_min = −0.45 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	−0.0717 (5)	−0.3479 (4)	−0.0069 (3)	0.0630 (15)
Br1	0.44042 (9)	0.37326 (8)	0.22953 (5)	0.0767 (4)
N1	−0.0588 (5)	−0.0520 (5)	0.1495 (3)	0.0442 (15)
C1	0.0218 (7)	−0.0187 (6)	0.2125 (4)	0.0487 (19)
H1A	0.0653	−0.0883	0.2333	0.058*
Br2	−0.32805 (9)	0.19580 (10)	0.38972 (4)	0.0806 (4)
N2	−0.1598 (6)	−0.2188 (5)	0.0521 (3)	0.0545 (17)
C2	0.1307 (7)	0.0670 (7)	0.2094 (4)	0.0470 (19)
C3	0.2514 (8)	0.0676 (7)	0.2534 (4)	0.060 (2)
H3A	0.2707	0.0050	0.2810	0.072*
C4	0.3449 (8)	0.1542 (8)	0.2592 (4)	0.061 (2)
H4A	0.4240	0.1510	0.2907	0.074*
C5	0.3201 (8)	0.2465 (7)	0.2176 (4)	0.055 (2)
C6	0.2044 (8)	0.2464 (7)	0.1691 (4)	0.054 (2)
H6A	0.1901	0.3043	0.1382	0.065*
C7	0.1108 (8)	0.1585 (7)	0.1676 (4)	0.057 (2)
H7A	0.0306	0.1615	0.1368	0.068*
C8	−0.0647 (7)	0.0317 (7)	0.2557 (4)	0.049 (2)
C9	−0.1647 (8)	0.1108 (7)	0.2339 (4)	0.054 (2)
H9A	−0.1798	0.1314	0.1908	0.065*
C10	−0.2433 (8)	0.1612 (7)	0.2714 (4)	0.055 (2)
H10A	−0.3092	0.2154	0.2548	0.067*
C11	−0.2210 (8)	0.1285 (7)	0.3351 (4)	0.056 (2)
C12	−0.1220 (8)	0.0515 (8)	0.3588 (4)	0.065 (2)
H12A	−0.1051	0.0326	0.4022	0.079*
C13	−0.0476 (8)	0.0019 (6)	0.3197 (4)	0.055 (2)
H13A	0.0165	−0.0536	0.3364	0.066*
C14	−0.1526 (7)	−0.1435 (7)	0.1605 (4)	0.057 (2)
H14A	−0.2085	−0.1157	0.1896	0.069*
H14B	−0.1009	−0.2089	0.1806	0.069*
C15	−0.2449 (8)	−0.1819 (7)	0.0968 (4)	0.061 (2)
H15A	−0.3026	−0.2449	0.1047	0.073*
H15B	−0.3027	−0.1185	0.0783	0.073*
C16	−0.0594 (8)	−0.1313 (7)	0.0440 (4)	0.064 (2)
H16A	−0.1059	−0.0643	0.0229	0.077*
H16B	−0.0008	−0.1616	0.0169	0.077*
C17	0.0250 (8)	−0.0964 (7)	0.1075 (4)	0.058 (2)
H17A	0.0757	−0.1624	0.1275	0.070*
H17B	0.0897	−0.0380	0.1009	0.070*
C18	−0.1507 (8)	−0.3269 (7)	0.0276 (4)	0.051 (2)
C19	−0.2448 (8)	−0.4138 (7)	0.0431 (4)	0.055 (2)
H19A	−0.3247	−0.3913	0.0552	0.066*
C20	−0.2158 (8)	−0.5239 (7)	0.0396 (3)	0.052 (2)
H20A	−0.1344	−0.5419	0.0276	0.063*
C21	−0.2995 (7)	−0.6208 (7)	0.0530 (3)	0.0483 (19)
C22	−0.4292 (8)	−0.6105 (7)	0.0646 (4)	0.060 (2)
H22A	−0.4668	−0.5376	0.0657	0.072*
C23	−0.5059 (9)	−0.7074 (8)	0.0748 (4)	0.064 (2)
H23A	−0.5935	−0.6976	0.0819	0.076*
C24	−0.4521 (9)	−0.8183 (8)	0.0743 (4)	0.059 (2)
C25	−0.3214 (9)	−0.8263 (7)	0.0645 (4)	0.066 (2)
H25A	−0.2823	−0.8989	0.0651	0.079*
C26	−0.2454 (8)	−0.7326 (7)	0.0538 (3)	0.055 (2)
H26A	−0.1576	−0.7432	0.0471	0.066*
C27	−0.5351 (9)	−0.9212 (8)	0.0868 (4)	0.093 (3)
H27A	−0.4845	−0.9904	0.0840	0.139*
H27B	−0.6185	−0.9234	0.0554	0.139*
H27C	−0.5551	−0.9152	0.1290	0.139*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O	0.078 (4)	0.049 (4)	0.070 (4)	−0.004 (3)	0.032 (3)	−0.014 (3)
Br1	0.0687 (6)	0.0546 (6)	0.1100 (8)	−0.0143 (5)	0.0262 (5)	−0.0154 (6)
N1	0.048 (4)	0.029 (3)	0.062 (4)	−0.009 (3)	0.026 (3)	−0.016 (3)
C1	0.045 (4)	0.031 (4)	0.068 (5)	−0.002 (4)	0.008 (4)	0.008 (4)
Br2	0.0783 (7)	0.1131 (9)	0.0545 (5)	−0.0146 (6)	0.0232 (5)	−0.0214 (6)
N2	0.055 (4)	0.042 (4)	0.073 (4)	−0.009 (3)	0.029 (3)	−0.014 (4)
C2	0.038 (4)	0.035 (5)	0.066 (5)	0.002 (4)	0.005 (4)	0.003 (4)
C3	0.063 (6)	0.043 (5)	0.076 (6)	0.006 (5)	0.018 (5)	0.012 (5)
C4	0.043 (5)	0.073 (7)	0.069 (6)	0.004 (4)	0.011 (4)	−0.026 (5)
C5	0.054 (5)	0.036 (5)	0.083 (6)	−0.002 (4)	0.034 (5)	0.001 (5)
C6	0.049 (5)	0.046 (5)	0.069 (5)	0.002 (4)	0.018 (4)	0.002 (4)
C7	0.059 (5)	0.049 (6)	0.063 (5)	0.009 (4)	0.015 (4)	−0.006 (4)
C8	0.052 (5)	0.039 (5)	0.055 (5)	−0.001 (4)	0.007 (4)	−0.002 (4)
C9	0.064 (5)	0.055 (6)	0.041 (4)	0.001 (5)	0.005 (4)	0.000 (4)
C10	0.065 (5)	0.054 (6)	0.049 (5)	0.008 (4)	0.015 (4)	0.001 (4)
C11	0.069 (5)	0.056 (5)	0.046 (5)	−0.019 (5)	0.015 (4)	−0.006 (4)
C12	0.073 (6)	0.079 (7)	0.043 (5)	−0.010 (6)	0.009 (5)	0.003 (5)
C13	0.059 (5)	0.049 (5)	0.054 (5)	−0.003 (4)	0.002 (4)	0.004 (4)
C14	0.052 (5)	0.056 (6)	0.069 (6)	−0.007 (4)	0.023 (4)	−0.002 (5)
C15	0.065 (5)	0.039 (5)	0.087 (6)	−0.006 (4)	0.035 (5)	−0.020 (5)
C16	0.087 (6)	0.045 (5)	0.076 (6)	−0.002 (5)	0.051 (5)	−0.006 (5)
C17	0.057 (5)	0.049 (6)	0.073 (6)	0.005 (4)	0.025 (5)	−0.006 (4)
C18	0.056 (5)	0.044 (5)	0.055 (5)	0.008 (4)	0.014 (4)	−0.010 (4)
C19	0.052 (5)	0.045 (5)	0.064 (5)	−0.001 (4)	0.004 (4)	−0.009 (4)
C20	0.064 (5)	0.047 (5)	0.044 (5)	−0.003 (4)	0.004 (4)	0.003 (4)
C21	0.055 (5)	0.049 (5)	0.040 (4)	0.008 (5)	0.007 (4)	−0.009 (4)
C22	0.073 (6)	0.045 (6)	0.067 (6)	0.004 (4)	0.026 (5)	−0.003 (4)
C23	0.067 (6)	0.062 (6)	0.063 (5)	0.013 (5)	0.017 (4)	0.011 (5)
C24	0.079 (6)	0.052 (6)	0.048 (5)	−0.003 (5)	0.014 (5)	0.002 (4)
C25	0.091 (7)	0.038 (5)	0.069 (6)	0.010 (5)	0.017 (5)	0.004 (5)
C26	0.065 (5)	0.047 (6)	0.053 (5)	0.008 (5)	0.013 (4)	0.007 (4)
C27	0.102 (8)	0.078 (7)	0.094 (7)	−0.022 (6)	0.009 (6)	0.015 (6)

Geometric parameters (Å, º) top

O—C18	1.210 (8)	C13—H13A	0.9300
Br1—C5	1.890 (7)	C14—C15	1.544 (10)
N1—C17	1.441 (8)	C14—H14A	0.9700
N1—C1	1.470 (8)	C14—H14B	0.9700
N1—C14	1.472 (8)	C15—H15A	0.9700
C1—C2	1.491 (9)	C15—H15B	0.9700
C1—C8	1.506 (9)	C16—C17	1.496 (10)
C1—H1A	0.9800	C16—H16A	0.9700
Br2—C11	1.904 (8)	C16—H16B	0.9700
N2—C18	1.370 (9)	C17—H17A	0.9700
N2—C15	1.466 (8)	C17—H17B	0.9700
N2—C16	1.466 (9)	C18—C19	1.466 (10)
C2—C3	1.373 (9)	C19—C20	1.317 (10)
C2—C7	1.374 (10)	C19—H19A	0.9300
C3—C4	1.365 (10)	C20—C21	1.468 (10)
C3—H3A	0.9300	C20—H20A	0.9300
C4—C5	1.381 (10)	C21—C22	1.380 (9)
C4—H4A	0.9300	C21—C26	1.408 (9)
C5—C6	1.389 (10)	C22—C23	1.406 (10)
C6—C7	1.385 (9)	C22—H22A	0.9300
C6—H6A	0.9300	C23—C24	1.398 (10)
C7—H7A	0.9300	C23—H23A	0.9300
C8—C9	1.370 (9)	C24—C25	1.375 (11)
C8—C13	1.380 (9)	C24—C27	1.513 (11)
C9—C10	1.364 (10)	C25—C26	1.374 (10)
C9—H9A	0.9300	C25—H25A	0.9300
C10—C11	1.380 (10)	C26—H26A	0.9300
C10—H10A	0.9300	C27—H27A	0.9600
C11—C12	1.356 (10)	C27—H27B	0.9600
C12—C13	1.354 (10)	C27—H27C	0.9600
C12—H12A	0.9300

C17—N1—C1	112.1 (6)	H14A—C14—H14B	108.0
C17—N1—C14	108.3 (6)	N2—C15—C14	109.1 (6)
C1—N1—C14	107.3 (6)	N2—C15—H15A	109.9
N1—C1—C2	114.1 (6)	C14—C15—H15A	109.9
N1—C1—C8	112.3 (6)	N2—C15—H15B	109.9
C2—C1—C8	106.7 (6)	C14—C15—H15B	109.9
N1—C1—H1A	107.9	H15A—C15—H15B	108.3
C2—C1—H1A	107.9	N2—C16—C17	111.1 (6)
C8—C1—H1A	107.9	N2—C16—H16A	109.4
C18—N2—C15	127.4 (6)	C17—C16—H16A	109.4
C18—N2—C16	119.4 (6)	N2—C16—H16B	109.4
C15—N2—C16	112.3 (6)	C17—C16—H16B	109.4
C3—C2—C7	115.4 (7)	H16A—C16—H16B	108.0
C3—C2—C1	121.9 (7)	N1—C17—C16	111.1 (6)
C7—C2—C1	122.3 (7)	N1—C17—H17A	109.4
C4—C3—C2	124.3 (8)	C16—C17—H17A	109.4
C4—C3—H3A	117.9	N1—C17—H17B	109.4
C2—C3—H3A	117.9	C16—C17—H17B	109.4
C3—C4—C5	118.9 (8)	H17A—C17—H17B	108.0
C3—C4—H4A	120.6	O—C18—N2	121.2 (8)
C5—C4—H4A	120.6	O—C18—C19	121.9 (7)
C4—C5—C6	119.3 (7)	N2—C18—C19	116.8 (7)
C4—C5—Br1	119.5 (7)	C20—C19—C18	119.8 (8)
C6—C5—Br1	121.1 (6)	C20—C19—H19A	120.1
C7—C6—C5	118.7 (8)	C18—C19—H19A	120.1
C7—C6—H6A	120.7	C19—C20—C21	126.3 (8)
C5—C6—H6A	120.7	C19—C20—H20A	116.8
C2—C7—C6	123.2 (8)	C21—C20—H20A	116.8
C2—C7—H7A	118.4	C22—C21—C26	117.0 (8)
C6—C7—H7A	118.4	C22—C21—C20	124.6 (7)
C9—C8—C13	116.0 (7)	C26—C21—C20	118.4 (7)
C9—C8—C1	122.0 (7)	C21—C22—C23	121.7 (8)
C13—C8—C1	122.1 (7)	C21—C22—H22A	119.1
C10—C9—C8	124.2 (7)	C23—C22—H22A	119.1
C10—C9—H9A	117.9	C24—C23—C22	120.8 (8)
C8—C9—H9A	117.9	C24—C23—H23A	119.6
C9—C10—C11	117.2 (8)	C22—C23—H23A	119.6
C9—C10—H10A	121.4	C25—C24—C23	116.5 (8)
C11—C10—H10A	121.4	C25—C24—C27	123.5 (9)
C12—C11—C10	120.5 (8)	C23—C24—C27	120.0 (8)
C12—C11—Br2	120.5 (6)	C26—C25—C24	123.5 (8)
C10—C11—Br2	119.0 (7)	C26—C25—H25A	118.3
C13—C12—C11	120.5 (8)	C24—C25—H25A	118.3
C13—C12—H12A	119.7	C25—C26—C21	120.5 (8)
C11—C12—H12A	119.7	C25—C26—H26A	119.8
C12—C13—C8	121.6 (8)	C21—C26—H26A	119.8
C12—C13—H13A	119.2	C24—C27—H27A	109.5
C8—C13—H13A	119.2	C24—C27—H27B	109.5
N1—C14—C15	111.0 (6)	H27A—C27—H27B	109.5
N1—C14—H14A	109.4	C24—C27—H27C	109.5
C15—C14—H14A	109.4	H27A—C27—H27C	109.5
N1—C14—H14B	109.4	H27B—C27—H27C	109.5
C15—C14—H14B	109.4

C17—N1—C1—C2	56.4 (8)	C1—C8—C13—C12	177.1 (7)
C14—N1—C1—C2	175.1 (6)	C17—N1—C14—C15	−60.4 (8)
C17—N1—C1—C8	177.9 (6)	C1—N1—C14—C15	178.4 (6)
C14—N1—C1—C8	−63.3 (7)	C18—N2—C15—C14	115.6 (8)
N1—C1—C2—C3	−147.5 (7)	C16—N2—C15—C14	−53.0 (9)
C8—C1—C2—C3	87.9 (8)	N1—C14—C15—N2	56.5 (8)
N1—C1—C2—C7	40.7 (10)	C18—N2—C16—C17	−115.1 (8)
C8—C1—C2—C7	−83.8 (9)	C15—N2—C16—C17	54.5 (8)
C7—C2—C3—C4	3.4 (12)	C1—N1—C17—C16	179.2 (6)
C1—C2—C3—C4	−168.9 (7)	C14—N1—C17—C16	61.0 (8)
C2—C3—C4—C5	−1.7 (12)	N2—C16—C17—N1	−58.5 (8)
C3—C4—C5—C6	−3.1 (11)	C15—N2—C18—O	−176.7 (7)
C3—C4—C5—Br1	174.6 (6)	C16—N2—C18—O	−8.8 (11)
C4—C5—C6—C7	5.9 (11)	C15—N2—C18—C19	5.8 (11)
Br1—C5—C6—C7	−171.7 (5)	C16—N2—C18—C19	173.7 (7)
C3—C2—C7—C6	−0.3 (11)	O—C18—C19—C20	24.1 (12)
C1—C2—C7—C6	172.0 (7)	N2—C18—C19—C20	−158.4 (7)
C5—C6—C7—C2	−4.3 (12)	C18—C19—C20—C21	−179.5 (7)
N1—C1—C8—C9	−44.2 (9)	C19—C20—C21—C22	7.4 (12)
C2—C1—C8—C9	81.4 (9)	C19—C20—C21—C26	−173.0 (8)
N1—C1—C8—C13	136.3 (7)	C26—C21—C22—C23	−2.0 (11)
C2—C1—C8—C13	−98.1 (8)	C20—C21—C22—C23	177.6 (7)
C13—C8—C9—C10	1.3 (11)	C21—C22—C23—C24	0.8 (12)
C1—C8—C9—C10	−178.2 (7)	C22—C23—C24—C25	0.9 (11)
C8—C9—C10—C11	−1.0 (12)	C22—C23—C24—C27	178.7 (8)
C9—C10—C11—C12	1.7 (12)	C23—C24—C25—C26	−1.6 (12)
C9—C10—C11—Br2	−179.9 (5)	C27—C24—C25—C26	−179.2 (8)
C10—C11—C12—C13	−2.9 (12)	C24—C25—C26—C21	0.5 (12)
Br2—C11—C12—C13	178.7 (6)	C22—C21—C26—C25	1.3 (11)
C11—C12—C13—C8	3.3 (12)	C20—C21—C26—C25	−178.3 (7)
C9—C8—C13—C12	−2.4 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20A···Oⁱ	0.93	2.55	3.445 (10)	162

Symmetry code: (i) −x, −y−1, −z.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₆Br₂N₂O
M_r	554.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.050 (2), 11.622 (2), 21.259 (4)
β (°)	101.72 (3)
V (Å³)	2431.3 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.36
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	0.553, 0.730
No. of measured, independent and observed [I > 2σ(I)] reflections	4720, 4452, 1998
R_int	0.097
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.155, 1.00
No. of reflections	4452
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.45

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
C20—H20A···Oⁱ	0.93	2.55	3.445 (10)	162

Symmetry code: (i) −x, −y−1, −z.

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

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Volume 68| Part 3| March 2012| Page o605

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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-methyl­phen­yl)prop-2-en-1-one

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