(E)-3-(2-Eth­oxy­phen­yl)-1-{4-[(2-fluoro­phen­yl)(4-fluoro­phen­yl)meth­yl]piperazin-1-yl}prop-2-en-1-one

Zhong, Y.; Wu, B.

doi:10.1107/S1600536812024130

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1975

doi:10.1107/S1600536812024130

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(E)-3-(2-Ethoxyphenyl)-1-{4-[(2-fluorophenyl)(4-fluorophenyl)methyl]piperazin-1-yl}prop-2-en-1-one

Yan Zhong ^a and Bin Wu ^b ^*

^aSchool of Chemistry and Chemical Engineering, Southeast University, Sipailou No. 2 Nanjing, Nanjing 210096, People's Republic of China, and ^bSchool 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 21 May 2012; accepted 26 May 2012; online 31 May 2012)

In the title compound, C₂₈H₂₈F₂N₂O₂, the piperazine ring has a chair conformation with the pendant N—C bonds in equatorial orientations. The C=C double bond has an E conformation and the dihedral angle between the fluorobenzene rings is 70.8 (3)°. In the crystal, molecules are linked by C—H⋯O and C—H⋯F hydrogen bonds.

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

C₂₈H₂₈F₂N₂O₂
M_r = 462.52
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.8550 (18) Å
b = 12.827 (3) Å
c = 22.432 (5) Å
V = 2547.9 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.975, T_max = 0.992
5217 measured reflections
2677 independent reflections
1328 reflections with I > 2σ(I)
R_int = 0.092
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.160
S = 1.00
2677 reflections
307 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O1ⁱ	0.93	2.44	3.316 (6)	156
C15—H15A⋯F2ⁱⁱ	0.97	2.36	3.241 (6)	150
C25—H25A⋯F1ⁱⁱⁱ	0.93	2.55	3.166 (7)	124
Symmetry codes: (i) x, y-1, z; (ii) $[-x+{\script{3\over 2}}, -y, z-{\script{1\over 2}}]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812024130/hb6812sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812024130/hb6812Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812024130/hb6812Isup3.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 [1.296 (6)]. The piperazine ring adopts a chair conformation with puchering parameters Q = 0.498 (6), Theta = 8.6 (6), Phi = 136 (4). The molecular structure is stabilized by intramolecular C—H···O and C—H···F hydrogen bonds. In the crystal, molecules are linked by intermolecular C—H···O and C—H···F hydrogen bonds.

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-(2-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-((2-fluorophenyl)(4-fluorophenyl)methyl)piperazine (1.730 g; 6 mmol) in the presence of triethylamine (5 ml) for 12 h at room temperature. The resultant mixture was cooled. The solid, (E)-3-(2-ethoxyphenyl)-1-(4-((2- fluorophenyl)(4-fluorophenyl)methyl)piperazin-1-yl)prop-2-en-1-one obtained was filtered and was recrystallized from ethanol. The colorless single crystals of the title compound used in x-ray diffraction studies were grown in ethanol by a slow evaporation at room temperature.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1989); 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)-3-(2-Ethoxyphenyl)-1-{4-[(2-fluorophenyl)(4- fluorophenyl)methyl]piperazin-1-yl}prop-2-en-1-one top

Crystal data top

C₂₈H₂₈F₂N₂O₂	D_x = 1.206 Mg m⁻³
M_r = 462.52	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 25 reflections
a = 8.8550 (18) Å	θ = 9–13°
b = 12.827 (3) Å	µ = 0.09 mm⁻¹
c = 22.432 (5) Å	T = 293 K
V = 2547.9 (9) Å³	Block, colorless
Z = 4	0.30 × 0.20 × 0.10 mm
F(000) = 976

Data collection top

Enraf–Nonius CAD-4 diffractometer	1328 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.092
Graphite monochromator	θ_max = 25.5°, θ_min = 1.8°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→15
T_min = 0.975, T_max = 0.992	l = −27→27
5217 measured reflections	3 standard reflections every 200 reflections
2677 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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.063P)²] where P = (F_o² + 2F_c²)/3
2677 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.23 e Å⁻³
1 restraint	Δρ_min = −0.12 e Å⁻³

Crystal data top

C₂₈H₂₈F₂N₂O₂	V = 2547.9 (9) Å³
M_r = 462.52	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.8550 (18) Å	µ = 0.09 mm⁻¹
b = 12.827 (3) Å	T = 293 K
c = 22.432 (5) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1328 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.092
T_min = 0.975, T_max = 0.992	3 standard reflections every 200 reflections
5217 measured reflections	intensity decay: 1%
2677 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	1 restraint
wR(F²) = 0.160	H-atom parameters constrained
S = 1.00	Δρ_max = 0.23 e Å⁻³
2677 reflections	Δρ_min = −0.12 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
O1	0.7258 (5)	0.3977 (2)	0.63108 (15)	0.0891 (11)
N1	0.7411 (6)	0.0370 (2)	0.69576 (16)	0.0739 (10)
F1	1.0297 (5)	−0.2050 (3)	0.6989 (2)	0.1490 (16)
C1	0.8192 (7)	−0.0465 (4)	0.7234 (2)	0.0846 (16)
H1A	0.9274	−0.0383	0.7154	0.102*
O2	0.7460 (6)	0.6004 (3)	0.46140 (16)	0.1160 (13)
F2	0.7518 (6)	−0.0447 (3)	0.97218 (14)	0.1447 (15)
N2	0.6907 (7)	0.2261 (3)	0.63068 (19)	0.113 (2)
C2	0.7675 (8)	−0.1522 (3)	0.6976 (2)	0.0780 (15)
C3	0.6258 (10)	−0.1824 (6)	0.6896 (3)	0.109 (2)
H3A	0.5466	−0.1367	0.6972	0.131*
C4	0.5969 (12)	−0.2819 (9)	0.6698 (3)	0.140 (3)
H4A	0.4976	−0.3038	0.6647	0.168*
C5	0.7119 (15)	−0.3482 (4)	0.6578 (3)	0.132 (4)
H5A	0.6893	−0.4150	0.6443	0.159*
C6	0.8589 (12)	−0.3209 (8)	0.6649 (4)	0.146 (4)
H6A	0.9384	−0.3656	0.6559	0.175*
C7	0.8803 (9)	−0.2219 (7)	0.6862 (3)	0.105 (2)
C8	0.7955 (9)	−0.0479 (4)	0.7912 (3)	0.0894 (18)
C9	0.9141 (8)	−0.0567 (5)	0.8273 (4)	0.105 (2)
H9A	1.0092	−0.0654	0.8104	0.126*
C10	0.9031 (10)	−0.0537 (6)	0.8849 (4)	0.111 (2)
H10A	0.9901	−0.0560	0.9081	0.133*
C11	0.7695 (11)	−0.0476 (4)	0.9110 (3)	0.0878 (16)
C12	0.6397 (8)	−0.0441 (5)	0.8813 (3)	0.1040 (19)
H12A	0.5471	−0.0432	0.9008	0.125*
C13	0.6508 (8)	−0.0417 (5)	0.8162 (3)	0.0949 (18)
H13A	0.5652	−0.0363	0.7924	0.114*
C14	0.7528 (7)	0.0413 (3)	0.6316 (2)	0.0761 (13)
H14A	0.7235	−0.0256	0.6152	0.091*
H14B	0.8574	0.0536	0.6208	0.091*
C15	0.6571 (8)	0.1243 (4)	0.6045 (2)	0.101 (2)
H15A	0.6751	0.1268	0.5618	0.121*
H15B	0.5514	0.1077	0.6108	0.121*
C16	0.6743 (8)	0.2221 (4)	0.6953 (2)	0.106 (2)
H16A	0.7091	0.2873	0.7124	0.127*
H16B	0.5684	0.2140	0.7053	0.127*
C17	0.7575 (8)	0.1385 (3)	0.7205 (2)	0.0914 (17)
H17A	0.7310	0.1344	0.7624	0.110*
H17B	0.8637	0.1568	0.7184	0.110*
C18	0.7198 (8)	0.3163 (4)	0.6033 (2)	0.0939 (19)
C19	0.7188 (7)	0.3198 (4)	0.5371 (2)	0.0975 (19)
H19A	0.7115	0.2575	0.5160	0.117*
C20	0.7279 (7)	0.4064 (3)	0.5076 (2)	0.0801 (14)
H20A	0.7312	0.4669	0.5304	0.096*
C21	0.7336 (6)	0.4210 (3)	0.4434 (2)	0.0707 (12)
C22	0.7270 (9)	0.3415 (4)	0.4028 (2)	0.102 (2)
H22A	0.7167	0.2738	0.4170	0.123*
C23	0.7348 (8)	0.3568 (5)	0.3411 (3)	0.1042 (17)
H23A	0.7331	0.3005	0.3150	0.125*
C24	0.7448 (7)	0.4536 (5)	0.3208 (2)	0.0986 (17)
H24A	0.7495	0.4650	0.2799	0.118*
C25	0.7485 (7)	0.5382 (4)	0.3591 (2)	0.0975 (16)
H25A	0.7540	0.6055	0.3438	0.117*
C26	0.7439 (7)	0.5228 (4)	0.4206 (2)	0.0794 (13)
C27	0.7553 (18)	0.7032 (5)	0.4448 (3)	0.213 (5)
H27A	0.6688	0.7217	0.4205	0.255*
H27B	0.8461	0.7145	0.4214	0.255*
C28	0.759 (2)	0.7692 (5)	0.4994 (5)	0.269 (8)
H28A	0.7702	0.8410	0.4882	0.403*
H28B	0.8428	0.7487	0.5239	0.403*
H28C	0.6667	0.7603	0.5212	0.403*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.134 (3)	0.0448 (16)	0.088 (2)	−0.009 (2)	−0.015 (3)	0.0009 (17)
N1	0.129 (3)	0.0314 (16)	0.061 (2)	0.001 (3)	−0.015 (3)	0.0062 (15)
F1	0.148 (3)	0.102 (3)	0.197 (4)	0.038 (3)	0.015 (3)	0.023 (3)
C1	0.126 (4)	0.059 (3)	0.069 (3)	0.017 (3)	0.009 (3)	−0.001 (3)
O2	0.209 (4)	0.0492 (18)	0.090 (2)	0.002 (3)	0.014 (4)	0.0069 (18)
F2	0.249 (4)	0.117 (2)	0.068 (2)	0.020 (4)	−0.015 (3)	0.0211 (18)
N2	0.238 (6)	0.0337 (19)	0.067 (3)	0.002 (3)	−0.012 (3)	0.0035 (19)
C2	0.127 (5)	0.042 (2)	0.065 (3)	0.003 (4)	0.000 (4)	0.004 (2)
C3	0.145 (6)	0.099 (5)	0.083 (4)	0.012 (5)	0.009 (5)	−0.019 (4)
C4	0.189 (8)	0.134 (8)	0.098 (6)	−0.044 (7)	−0.042 (5)	0.021 (6)
C5	0.288 (13)	0.036 (3)	0.072 (4)	0.000 (6)	−0.044 (7)	0.007 (3)
C6	0.217 (10)	0.113 (7)	0.108 (6)	0.111 (7)	−0.026 (7)	−0.020 (5)
C7	0.127 (5)	0.120 (6)	0.068 (4)	0.027 (5)	0.016 (4)	0.018 (4)
C8	0.152 (6)	0.041 (2)	0.075 (4)	0.015 (3)	0.004 (4)	0.011 (2)
C9	0.119 (5)	0.071 (4)	0.124 (7)	−0.006 (4)	−0.011 (5)	−0.008 (4)
C10	0.152 (7)	0.094 (5)	0.088 (5)	−0.003 (5)	−0.026 (5)	−0.015 (4)
C11	0.131 (5)	0.057 (3)	0.076 (4)	0.007 (4)	−0.019 (5)	0.013 (3)
C12	0.121 (5)	0.080 (4)	0.110 (6)	0.007 (4)	−0.006 (5)	0.008 (4)
C13	0.129 (5)	0.068 (3)	0.087 (5)	0.028 (4)	−0.029 (4)	0.002 (4)
C14	0.124 (4)	0.040 (2)	0.064 (3)	0.016 (3)	0.010 (3)	−0.001 (2)
C15	0.176 (6)	0.061 (3)	0.066 (3)	−0.004 (4)	−0.013 (3)	0.002 (3)
C16	0.211 (7)	0.055 (3)	0.050 (3)	0.017 (4)	−0.006 (4)	−0.001 (3)
C17	0.163 (5)	0.045 (2)	0.066 (3)	−0.042 (4)	−0.015 (4)	−0.001 (2)
C18	0.172 (6)	0.041 (2)	0.069 (3)	0.016 (4)	−0.025 (4)	−0.002 (2)
C19	0.173 (6)	0.047 (2)	0.073 (3)	0.001 (4)	0.010 (4)	0.001 (2)
C20	0.120 (4)	0.047 (2)	0.073 (3)	0.000 (3)	−0.001 (3)	0.010 (2)
C21	0.089 (3)	0.056 (3)	0.067 (3)	−0.007 (3)	−0.003 (3)	0.007 (2)
C22	0.162 (6)	0.062 (3)	0.083 (4)	−0.001 (4)	−0.038 (5)	−0.002 (3)
C23	0.135 (5)	0.084 (4)	0.094 (4)	0.002 (4)	0.001 (5)	−0.008 (3)
C24	0.121 (4)	0.095 (4)	0.080 (3)	0.027 (5)	0.011 (4)	−0.006 (3)
C25	0.136 (4)	0.078 (3)	0.078 (3)	0.006 (5)	0.015 (4)	0.025 (3)
C26	0.106 (4)	0.060 (3)	0.072 (3)	0.007 (4)	0.001 (4)	0.009 (2)
C27	0.456 (17)	0.060 (4)	0.122 (6)	−0.052 (9)	−0.010 (10)	0.022 (4)
C28	0.60 (2)	0.067 (4)	0.137 (7)	−0.016 (10)	−0.001 (13)	−0.008 (5)

Geometric parameters (Å, º) top

O1—C18	1.216 (5)	C13—H13A	0.9300
N1—C1	1.417 (6)	C14—C15	1.490 (7)
N1—C17	1.423 (5)	C14—H14A	0.9700
N1—C14	1.444 (6)	C14—H14B	0.9700
F1—C7	1.371 (8)	C15—H15A	0.9700
C1—C8	1.536 (7)	C15—H15B	0.9700
C1—C2	1.545 (7)	C16—C17	1.417 (7)
C1—H1A	0.9800	C16—H16A	0.9700
O2—C26	1.351 (6)	C16—H16B	0.9700
O2—C27	1.374 (7)	C17—H17A	0.9700
F2—C11	1.383 (7)	C17—H17B	0.9700
N2—C18	1.335 (7)	C18—C19	1.488 (7)
N2—C16	1.458 (6)	C19—C20	1.296 (6)
N2—C15	1.463 (7)	C19—H19A	0.9300
C2—C3	1.325 (9)	C20—C21	1.452 (6)
C2—C7	1.365 (9)	C20—H20A	0.9300
C3—C4	1.375 (12)	C21—C22	1.368 (7)
C3—H3A	0.9300	C21—C26	1.406 (6)
C4—C5	1.354 (13)	C22—C23	1.401 (7)
C4—H4A	0.9300	C22—H22A	0.9300
C5—C6	1.358 (12)	C23—C24	1.325 (8)
C5—H5A	0.9300	C23—H23A	0.9300
C6—C7	1.370 (12)	C24—C25	1.385 (7)
C6—H6A	0.9300	C24—H24A	0.9300
C8—C9	1.331 (8)	C25—C26	1.394 (7)
C8—C13	1.401 (9)	C25—H25A	0.9300
C9—C10	1.296 (8)	C27—C28	1.489 (11)
C9—H9A	0.9300	C27—H27A	0.9700
C10—C11	1.323 (9)	C27—H27B	0.9700
C10—H10A	0.9300	C28—H28A	0.9600
C11—C12	1.328 (8)	C28—H28B	0.9600
C12—C13	1.463 (8)	C28—H28C	0.9600
C12—H12A	0.9300

C1—N1—C17	118.1 (4)	N2—C15—H15A	109.5
C1—N1—C14	115.4 (4)	C14—C15—H15A	109.5
C17—N1—C14	110.2 (3)	N2—C15—H15B	109.5
N1—C1—C8	112.0 (4)	C14—C15—H15B	109.5
N1—C1—C2	110.8 (4)	H15A—C15—H15B	108.0
C8—C1—C2	108.7 (4)	C17—C16—N2	111.8 (5)
N1—C1—H1A	108.4	C17—C16—H16A	109.3
C8—C1—H1A	108.4	N2—C16—H16A	109.3
C2—C1—H1A	108.4	C17—C16—H16B	109.3
C26—O2—C27	121.6 (5)	N2—C16—H16B	109.3
C18—N2—C16	120.4 (4)	H16A—C16—H16B	107.9
C18—N2—C15	129.0 (4)	C16—C17—N1	118.9 (5)
C16—N2—C15	110.4 (4)	C16—C17—H17A	107.6
C3—C2—C7	118.5 (6)	N1—C17—H17A	107.6
C3—C2—C1	126.0 (6)	C16—C17—H17B	107.6
C7—C2—C1	115.3 (6)	N1—C17—H17B	107.6
C2—C3—C4	119.4 (7)	H17A—C17—H17B	107.0
C2—C3—H3A	120.3	O1—C18—N2	121.2 (4)
C4—C3—H3A	120.3	O1—C18—C19	119.1 (4)
C5—C4—C3	120.5 (9)	N2—C18—C19	118.9 (4)
C5—C4—H4A	119.7	C20—C19—C18	122.4 (5)
C3—C4—H4A	119.7	C20—C19—H19A	118.8
C4—C5—C6	122.4 (8)	C18—C19—H19A	118.8
C4—C5—H5A	118.8	C19—C20—C21	128.2 (5)
C6—C5—H5A	118.8	C19—C20—H20A	115.9
C5—C6—C7	114.4 (7)	C21—C20—H20A	115.9
C5—C6—H6A	122.8	C22—C21—C26	116.9 (4)
C7—C6—H6A	122.8	C22—C21—C20	124.2 (4)
C2—C7—C6	124.8 (8)	C26—C21—C20	118.9 (4)
C2—C7—F1	124.3 (7)	C21—C22—C23	123.5 (5)
C6—C7—F1	110.7 (8)	C21—C22—H22A	118.3
C9—C8—C13	118.9 (6)	C23—C22—H22A	118.3
C9—C8—C1	119.7 (7)	C24—C23—C22	118.3 (6)
C13—C8—C1	121.4 (6)	C24—C23—H23A	120.8
C10—C9—C8	123.0 (7)	C22—C23—H23A	120.8
C10—C9—H9A	118.5	C23—C24—C25	121.5 (5)
C8—C9—H9A	118.5	C23—C24—H24A	119.3
C9—C10—C11	120.7 (7)	C25—C24—H24A	119.3
C9—C10—H10A	119.7	C24—C25—C26	120.2 (5)
C11—C10—H10A	119.7	C24—C25—H25A	119.9
C10—C11—C12	123.6 (6)	C26—C25—H25A	119.9
C10—C11—F2	122.9 (7)	O2—C26—C25	124.4 (4)
C12—C11—F2	113.5 (8)	O2—C26—C21	116.0 (4)
C11—C12—C13	116.3 (6)	C25—C26—C21	119.6 (5)
C11—C12—H12A	121.9	O2—C27—C28	108.9 (6)
C13—C12—H12A	121.9	O2—C27—H27A	109.9
C8—C13—C12	117.4 (6)	C28—C27—H27A	109.9
C8—C13—H13A	121.3	O2—C27—H27B	109.9
C12—C13—H13A	121.3	C28—C27—H27B	109.9
N1—C14—C15	113.2 (4)	H27A—C27—H27B	108.3
N1—C14—H14A	108.9	C27—C28—H28A	109.5
C15—C14—H14A	108.9	C27—C28—H28B	109.5
N1—C14—H14B	108.9	H28A—C28—H28B	109.5
C15—C14—H14B	108.9	C27—C28—H28C	109.5
H14A—C14—H14B	107.8	H28A—C28—H28C	109.5
N2—C15—C14	110.9 (5)	H28B—C28—H28C	109.5

C17—N1—C1—C8	48.9 (7)	C1—N1—C14—C15	174.5 (5)
C14—N1—C1—C8	−177.6 (5)	C17—N1—C14—C15	−48.4 (7)
C17—N1—C1—C2	170.4 (5)	C18—N2—C15—C14	130.6 (7)
C14—N1—C1—C2	−56.1 (6)	C16—N2—C15—C14	−55.2 (8)
N1—C1—C2—C3	−47.6 (8)	N1—C14—C15—N2	55.0 (7)
C8—C1—C2—C3	75.9 (7)	C18—N2—C16—C17	−133.4 (7)
N1—C1—C2—C7	137.0 (5)	C15—N2—C16—C17	51.8 (8)
C8—C1—C2—C7	−99.5 (6)	N2—C16—C17—N1	−49.8 (9)
C7—C2—C3—C4	−0.4 (10)	C1—N1—C17—C16	−176.9 (6)
C1—C2—C3—C4	−175.6 (6)	C14—N1—C17—C16	47.4 (8)
C2—C3—C4—C5	−0.9 (11)	C16—N2—C18—O1	−3.7 (11)
C3—C4—C5—C6	0.4 (12)	C15—N2—C18—O1	170.0 (7)
C4—C5—C6—C7	1.3 (12)	C16—N2—C18—C19	−173.2 (6)
C3—C2—C7—C6	2.4 (10)	C15—N2—C18—C19	0.5 (11)
C1—C2—C7—C6	178.1 (7)	O1—C18—C19—C20	1.8 (11)
C3—C2—C7—F1	−172.3 (6)	N2—C18—C19—C20	171.5 (7)
C1—C2—C7—F1	3.4 (8)	C18—C19—C20—C21	177.6 (6)
C5—C6—C7—C2	−2.8 (12)	C19—C20—C21—C22	1.4 (11)
C5—C6—C7—F1	172.5 (7)	C19—C20—C21—C26	−179.8 (7)
N1—C1—C8—C9	−131.1 (6)	C26—C21—C22—C23	2.1 (11)
C2—C1—C8—C9	106.2 (7)	C20—C21—C22—C23	−179.0 (7)
N1—C1—C8—C13	49.9 (7)	C21—C22—C23—C24	−2.0 (13)
C2—C1—C8—C13	−72.9 (7)	C22—C23—C24—C25	0.4 (12)
C13—C8—C9—C10	−4.2 (10)	C23—C24—C25—C26	0.9 (11)
C1—C8—C9—C10	176.8 (6)	C27—O2—C26—C25	−1.0 (12)
C8—C9—C10—C11	3.9 (12)	C27—O2—C26—C21	−179.8 (9)
C9—C10—C11—C12	0.0 (11)	C24—C25—C26—O2	−179.6 (6)
C9—C10—C11—F2	179.7 (6)	C24—C25—C26—C21	−0.8 (11)
C10—C11—C12—C13	−3.2 (9)	C22—C21—C26—O2	178.2 (6)
F2—C11—C12—C13	177.1 (5)	C20—C21—C26—O2	−0.7 (9)
C9—C8—C13—C12	0.7 (9)	C22—C21—C26—C25	−0.7 (10)
C1—C8—C13—C12	179.8 (5)	C20—C21—C26—C25	−179.6 (6)
C11—C12—C13—C8	2.7 (9)	C26—O2—C27—C28	−178.7 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1ⁱ	0.93	2.44	3.316 (6)	156
C15—H15A···F2ⁱⁱ	0.97	2.36	3.241 (6)	150
C25—H25A···F1ⁱⁱⁱ	0.93	2.55	3.166 (7)	124

Symmetry codes: (i) x, y−1, z; (ii) −x+3/2, −y, z−1/2; (iii) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₈F₂N₂O₂
M_r	462.52
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	8.8550 (18), 12.827 (3), 22.432 (5)
V (Å³)	2547.9 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.975, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	5217, 2677, 1328
R_int	0.092
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.160, 1.00
No. of reflections	2677
No. of parameters	307
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.12

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
C5—H5A···O1ⁱ	0.93	2.44	3.316 (6)	156
C15—H15A···F2ⁱⁱ	0.97	2.36	3.241 (6)	150
C25—H25A···F1ⁱⁱⁱ	0.93	2.55	3.166 (7)	124

Symmetry codes: (i) x, y−1, z; (ii) −x+3/2, −y, z−1/2; (iii) x−1/2, −y+1/2, −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, o298. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 6| June 2012| Page o1975

doi:10.1107/S1600536812024130

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

(E)-3-(2-Eth­­oxy­phen­yl)-1-{4-[(2-fluoro­phen­yl)(4-fluoro­phen­yl)meth­yl]piperazin-1-yl}prop-2-en-1-one

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organic compounds

(E)-3-(2-Ethoxyphenyl)-1-{4-[(2-fluorophenyl)(4-fluorophenyl)methyl]piperazin-1-yl}prop-2-en-1-one