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

In the title compound, C(27)H(26)Br(2)N(2)O, 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 bromo-benzene rings is 83.0 (4)°. In the crystal, inversion dimers linked through pairs of C-H⋯O hydrogen bonds generate R(2) (2)(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 = 554.32

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.155

S = 1.00

4452 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.45 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/S1600536812003820/hb6616sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812003820/hb6616Isup3.cml

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

C27H26Br2N2O	F(000) = 1120
Mr = 554.32	Dx = 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

Enraf–Nonius CAD-4 diffractometer	1998 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.097
Graphite monochromator	θmax = 25.4°, θmin = 2.0°
ω/2θ scans	h = 0→12
Absorption correction: ψ scan (North et al., 1968)	k = 0→14
Tmin = 0.553, Tmax = 0.730	l = −25→25
4720 measured reflections	3 standard reflections every 200 reflections
4452 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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.058P)2] where P = (Fo2 + 2Fc2)/3
4452 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.45 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	−0.0717 (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*

	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)

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)

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

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) .