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

Teng, Y.-B.; Dai, Z.-H.; Wu, B.

doi:10.1107/S1600536811006210

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o697

doi:10.1107/S1600536811006210

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

Yan-Bo Teng,^a Zhao-Hui Dai ^a and Bin Wu ^a ^*

^aSchool 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 13 January 2011; accepted 18 February 2011; online 23 February 2011)

In the title compound, C₂₈H₂₉FN₂O₃, the conformation about the ethene bond is E. The piperazine ring adopts a chair conformation. In the crystal, molecules are linked by intermolecular C—H⋯O hydrogen bonds.

Related literature

For properties of cinnamic acid derivatives, see: Shi et al. (2005 ); Point et al. (1998 ). For synthetic procedures, see: Wu et al. (2008 ). For a related structure, see: Mouillé et al. (1975 ).

Experimental

Crystal data

C₂₈H₂₉FN₂O₃
M_r = 460.53
Monoclinic, P 2₁ /c
a = 10.235 (2) Å
b = 7.8420 (16) Å
c = 30.385 (6) Å
β = 96.65 (3)°
V = 2422.4 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.09 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 = 0.983, T_max = 0.991
4730 measured reflections
4463 independent reflections
2366 reflections with I > 2σ(I)
R_int = 0.031
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.170
S = 1.01
4463 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.18 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	2.28	3.131 (4)	152
C17—H17A⋯O3ⁱⁱ	0.93	2.60	3.499 (4)	163
Symmetry codes: (i) -x+1, -y-1, -z; (ii) x-1, y, z.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811006210/pv2381sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811006210/pv2381Isup2.hkl

checkCIF report

Comment top

Cinnamic acid derivatives have been reported to possess many useful properties, including alpha-glucosidase inhibition, acyl-CoA inhibition, LDL-oxidation inhibition, tyrosinase inhibition, antioxidant, antimicrobial, neuroprotective activities (Shi et al., 2005; Point et al., 1998). We report here the synthesis and crystal structure of a novel cinnamic acid derivative.

In the title molecule (Fig. 1), the conformation about the ethene bond C7═C8 is E. The piperazine ring adopts a chair conformation. There are intramolecular and intermolecular C—H···O hydrogen bonds in the title compound (Fig. 2) which consilidate the crystal structure. The bond lenths and angles in the title compound agree well with the corresponding bond lengths and angles in a closely related compound, trans-cinnamyl-1-diphenylmethyl-4-piperazine (Mouillé et al., 1975).

Related literature top

For properties of cinnamic acid derivatives, see: Shi et al. (2005); Point et al. (1998). For synthetic procedures, see: Wu et al. (2008). For a related structure, see: Mouillé et al. (1975).

Experimental top

The synthesis follows the method of Wu et al. (2008). A mixture of (E)-3-(4-fluoro phenyl)acrylic acid (1.66 g; 10 mmol), dimethyl sulfoxide (4 ml) and dichloromethane (60 ml) was stirred for 6 h at room temperature. The solvent was removed under reduced pressure. The residue was dissolved in acetone (60 ml) and reacted with 1-(bis(4-methoxyphenyl)methyl) piperazine (4.69 g; 15 mmol) in the presence of triethylamine (12 ml) for 5 h at room temperature. The resultant mixture was cooled. The solid thus obtained was filtered and recrystallized from ethanol to afford the title compound. Pale-yellow single crystals of the title compound suitable for X-ray diffraction studies were grown from a mixture of CHCl₃ and hexane (1:1) by slow evaporation at room temperature.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labeling scheme and 70% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound showing hydrogen bonds as dashed lines.

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

Crystal data top

C₂₈H₂₉FN₂O₃	F(000) = 976
M_r = 460.53	D_x = 1.263 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 10.235 (2) Å	θ = 10–13°
b = 7.8420 (16) Å	µ = 0.09 mm⁻¹
c = 30.385 (6) Å	T = 293 K
β = 96.65 (3)°	Block, pale-yellow
V = 2422.4 (8) Å³	0.20 × 0.10 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	2366 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 25.4°, θ_min = 1.4°
ω and 2θ scans	h = 0→12
Absorption correction: multi-scan ψ scan	k = 0→9
T_min = 0.983, T_max = 0.991	l = −36→36
4730 measured reflections	3 standard reflections every 200 reflections
4463 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.170	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.080P)²] where P = (F_o² + 2F_c²)/3
4463 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₈H₂₉FN₂O₃	V = 2422.4 (8) Å³
M_r = 460.53	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.235 (2) Å	µ = 0.09 mm⁻¹
b = 7.8420 (16) Å	T = 293 K
c = 30.385 (6) Å	0.20 × 0.10 × 0.10 mm
β = 96.65 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2366 reflections with I > 2σ(I)
Absorption correction: multi-scan ψ scan	R_int = 0.031
T_min = 0.983, T_max = 0.991	3 standard reflections every 200 reflections
4730 measured reflections	intensity decay: 1%
4463 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.170	H-atom parameters constrained
S = 1.01	Δρ_max = 0.13 e Å⁻³
4463 reflections	Δρ_min = −0.18 e Å⁻³
307 parameters

Special details top

Experimental. (North et al., 1968)

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
F	1.1036 (2)	−0.8047 (3)	0.03071 (8)	0.1138 (8)
N1	0.5564 (2)	0.0310 (3)	0.08123 (8)	0.0606 (7)
O1	0.4552 (2)	−0.1690 (3)	0.03651 (7)	0.0783 (7)
C1	0.9101 (3)	−0.4669 (4)	0.06924 (11)	0.0723 (10)
H1A	0.9196	−0.3770	0.0893	0.087*
O2	0.06003 (19)	0.8563 (3)	0.14269 (7)	0.0658 (6)
N2	0.5216 (2)	0.3082 (3)	0.13971 (8)	0.0540 (6)
C2	1.0149 (4)	−0.5726 (5)	0.06570 (13)	0.0838 (11)
H2A	1.0948	−0.5563	0.0831	0.101*
O3	0.93784 (18)	0.7764 (3)	0.25379 (7)	0.0653 (6)
C3	0.9982 (4)	−0.7018 (5)	0.03591 (13)	0.0779 (10)
C4	0.8809 (4)	−0.7385 (5)	0.01176 (12)	0.0841 (11)
H4A	0.8712	−0.8333	−0.0067	0.101*
C5	0.7775 (4)	−0.6302 (5)	0.01579 (11)	0.0755 (10)
H5A	0.6967	−0.6512	−0.0007	0.091*
C6	0.7909 (3)	−0.4905 (4)	0.04381 (10)	0.0592 (8)
C7	0.6790 (3)	−0.3740 (4)	0.04508 (10)	0.0636 (9)
H7A	0.5982	−0.4155	0.0324	0.076*
C8	0.6773 (3)	−0.2193 (4)	0.06162 (10)	0.0619 (9)
H8A	0.7551	−0.1731	0.0755	0.074*
C9	0.5553 (3)	−0.1162 (4)	0.05889 (10)	0.0574 (8)
C10	0.4434 (3)	0.1440 (4)	0.07401 (10)	0.0677 (9)
H10A	0.3688	0.0814	0.0595	0.081*
H10B	0.4629	0.2365	0.0546	0.081*
C11	0.4086 (3)	0.2162 (4)	0.11695 (10)	0.0633 (9)
H11A	0.3345	0.2932	0.1112	0.076*
H11B	0.3834	0.1246	0.1357	0.076*
C12	0.6265 (3)	0.1835 (4)	0.15010 (11)	0.0662 (9)
H12A	0.5962	0.0944	0.1686	0.079*
H12B	0.7016	0.2387	0.1666	0.079*
C13	0.6676 (3)	0.1057 (4)	0.10871 (11)	0.0658 (9)
H13A	0.7075	0.1927	0.0919	0.079*
H13B	0.7331	0.0182	0.1167	0.079*
C14	0.4907 (3)	0.4005 (4)	0.17929 (9)	0.0539 (8)
H14A	0.4654	0.3170	0.2008	0.065*
C15	0.3763 (3)	0.5219 (4)	0.16789 (10)	0.0496 (7)
C16	0.2791 (3)	0.5383 (4)	0.19576 (10)	0.0562 (8)
H16A	0.2837	0.4723	0.2213	0.067*
C17	0.1757 (3)	0.6503 (4)	0.18645 (10)	0.0588 (8)
H17A	0.1113	0.6587	0.2056	0.071*
C18	0.1677 (3)	0.7490 (4)	0.14916 (10)	0.0517 (7)
C19	0.2627 (3)	0.7373 (4)	0.12093 (10)	0.0564 (8)
H19A	0.2579	0.8045	0.0956	0.068*
C20	0.3658 (3)	0.6239 (4)	0.13073 (10)	0.0576 (8)
H20A	0.4302	0.6165	0.1116	0.069*
C21	0.0545 (3)	0.9718 (4)	0.10672 (11)	0.0739 (10)
H21A	−0.0246	1.0382	0.1056	0.111*
H21B	0.0548	0.9093	0.0796	0.111*
H21C	0.1295	1.0461	0.1106	0.111*
C22	0.6118 (3)	0.4964 (4)	0.20031 (9)	0.0487 (7)
C23	0.6794 (3)	0.6068 (4)	0.17551 (10)	0.0654 (9)
H23A	0.6512	0.6209	0.1455	0.078*
C24	0.7869 (3)	0.6956 (4)	0.19426 (10)	0.0640 (9)
H24A	0.8311	0.7679	0.1768	0.077*
C25	0.8303 (3)	0.6793 (4)	0.23854 (10)	0.0516 (7)
C26	0.7663 (3)	0.5699 (4)	0.26369 (10)	0.0594 (8)
H26A	0.7956	0.5555	0.2936	0.071*
C27	0.6569 (3)	0.4799 (4)	0.24439 (10)	0.0583 (8)
H27A	0.6134	0.4066	0.2619	0.070*
C28	0.9994 (3)	0.7437 (5)	0.29707 (11)	0.0853 (11)
H28A	1.0722	0.8203	0.3037	0.128*
H28B	1.0305	0.6282	0.2989	0.128*
H28C	0.9372	0.7606	0.3180	0.128*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F	0.1173 (18)	0.1002 (17)	0.1298 (19)	0.0444 (15)	0.0391 (15)	0.0195 (15)
N1	0.0469 (15)	0.0636 (17)	0.0693 (17)	0.0060 (14)	−0.0021 (13)	−0.0110 (15)
O1	0.0608 (14)	0.0883 (17)	0.0834 (16)	−0.0077 (13)	−0.0015 (12)	−0.0212 (13)
C1	0.075 (2)	0.053 (2)	0.084 (2)	0.0013 (19)	−0.0119 (19)	−0.0117 (18)
O2	0.0542 (12)	0.0670 (14)	0.0768 (15)	0.0124 (12)	0.0106 (10)	0.0043 (12)
N2	0.0361 (13)	0.0562 (15)	0.0682 (16)	0.0014 (12)	−0.0003 (11)	−0.0075 (13)
C2	0.075 (2)	0.059 (2)	0.113 (3)	0.006 (2)	−0.010 (2)	−0.003 (2)
O3	0.0502 (12)	0.0750 (15)	0.0689 (14)	−0.0098 (12)	−0.0008 (10)	−0.0058 (12)
C3	0.087 (3)	0.067 (3)	0.083 (3)	0.019 (2)	0.026 (2)	0.017 (2)
C4	0.109 (3)	0.079 (3)	0.066 (2)	0.015 (3)	0.017 (2)	−0.018 (2)
C5	0.081 (2)	0.080 (3)	0.065 (2)	−0.004 (2)	0.0024 (18)	−0.019 (2)
C6	0.067 (2)	0.0534 (19)	0.0571 (18)	−0.0045 (17)	0.0063 (16)	−0.0043 (16)
C7	0.059 (2)	0.069 (2)	0.062 (2)	−0.0046 (18)	0.0049 (16)	−0.0068 (18)
C8	0.0550 (19)	0.060 (2)	0.070 (2)	−0.0064 (17)	0.0063 (15)	−0.0123 (18)
C9	0.0530 (19)	0.063 (2)	0.0568 (19)	−0.0047 (17)	0.0098 (15)	−0.0026 (17)
C10	0.0502 (18)	0.075 (2)	0.074 (2)	0.0085 (18)	−0.0097 (16)	−0.0102 (18)
C11	0.0391 (16)	0.067 (2)	0.081 (2)	0.0023 (16)	−0.0036 (15)	−0.0091 (18)
C12	0.0475 (18)	0.063 (2)	0.085 (2)	0.0043 (16)	−0.0082 (16)	−0.0163 (18)
C13	0.0429 (17)	0.064 (2)	0.089 (2)	0.0022 (16)	0.0026 (16)	−0.0136 (19)
C14	0.0489 (17)	0.0533 (18)	0.0598 (19)	−0.0024 (15)	0.0077 (14)	0.0045 (16)
C15	0.0384 (15)	0.0494 (17)	0.0606 (18)	−0.0038 (14)	0.0045 (13)	−0.0015 (15)
C16	0.0540 (18)	0.0579 (19)	0.0587 (18)	−0.0039 (16)	0.0150 (15)	0.0081 (16)
C17	0.0470 (17)	0.065 (2)	0.066 (2)	0.0046 (16)	0.0166 (15)	0.0020 (17)
C18	0.0414 (16)	0.0525 (18)	0.0610 (19)	−0.0016 (15)	0.0059 (14)	−0.0063 (16)
C19	0.0553 (18)	0.0559 (19)	0.0588 (19)	0.0031 (16)	0.0096 (15)	0.0058 (16)
C20	0.0430 (16)	0.067 (2)	0.066 (2)	0.0037 (16)	0.0170 (14)	0.0057 (17)
C21	0.059 (2)	0.074 (2)	0.088 (3)	0.0111 (18)	0.0009 (18)	0.006 (2)
C22	0.0414 (15)	0.0493 (17)	0.0557 (18)	0.0038 (14)	0.0063 (13)	−0.0022 (15)
C23	0.062 (2)	0.085 (2)	0.0485 (18)	−0.0180 (19)	0.0023 (15)	0.0081 (17)
C24	0.0528 (18)	0.079 (2)	0.061 (2)	−0.0176 (18)	0.0077 (15)	0.0101 (18)
C25	0.0406 (16)	0.0512 (18)	0.063 (2)	0.0044 (15)	0.0061 (15)	−0.0050 (16)
C26	0.0550 (18)	0.073 (2)	0.0476 (17)	0.0007 (18)	−0.0041 (15)	0.0037 (16)
C27	0.0533 (18)	0.062 (2)	0.0598 (19)	−0.0049 (17)	0.0067 (15)	0.0113 (17)
C28	0.063 (2)	0.100 (3)	0.086 (3)	−0.003 (2)	−0.0217 (19)	0.003 (2)

Geometric parameters (Å, º) top

F—C3	1.370 (4)	C12—H12A	0.9700
N1—C9	1.338 (4)	C12—H12B	0.9700
N1—C10	1.453 (4)	C13—H13A	0.9700
N1—C13	1.455 (4)	C13—H13B	0.9700
O1—C9	1.235 (3)	C14—C15	1.517 (4)
C1—C2	1.370 (4)	C14—C22	1.525 (4)
C1—C6	1.379 (4)	C14—H14A	0.9800
C1—H1A	0.9300	C15—C20	1.378 (4)
O2—C18	1.382 (3)	C15—C16	1.385 (4)
O2—C21	1.416 (3)	C16—C17	1.380 (4)
N2—C12	1.459 (3)	C16—H16A	0.9300
N2—C11	1.466 (3)	C17—C18	1.367 (4)
N2—C14	1.469 (3)	C17—H17A	0.9300
C2—C3	1.357 (5)	C18—C19	1.372 (4)
C2—H2A	0.9300	C19—C20	1.386 (4)
O3—C25	1.374 (3)	C19—H19A	0.9300
O3—C28	1.414 (3)	C20—H20A	0.9300
C3—C4	1.364 (5)	C21—H21A	0.9600
C4—C5	1.373 (5)	C21—H21B	0.9600
C4—H4A	0.9300	C21—H21C	0.9600
C5—C6	1.385 (4)	C22—C27	1.372 (4)
C5—H5A	0.9300	C22—C23	1.384 (4)
C6—C7	1.469 (4)	C23—C24	1.370 (4)
C7—C8	1.314 (4)	C23—H23A	0.9300
C7—H7A	0.9300	C24—C25	1.373 (4)
C8—C9	1.482 (4)	C24—H24A	0.9300
C8—H8A	0.9300	C25—C26	1.365 (4)
C10—C11	1.503 (4)	C26—C27	1.394 (4)
C10—H10A	0.9700	C26—H26A	0.9300
C10—H10B	0.9700	C27—H27A	0.9300
C11—H11A	0.9700	C28—H28A	0.9600
C11—H11B	0.9700	C28—H28B	0.9600
C12—C13	1.501 (4)	C28—H28C	0.9600

C9—N1—C10	119.3 (2)	C12—C13—H13B	109.3
C9—N1—C13	126.8 (3)	H13A—C13—H13B	108.0
C10—N1—C13	113.4 (2)	N2—C14—C15	110.8 (2)
C2—C1—C6	121.7 (3)	N2—C14—C22	110.1 (2)
C2—C1—H1A	119.2	C15—C14—C22	110.8 (2)
C6—C1—H1A	119.2	N2—C14—H14A	108.3
C18—O2—C21	117.3 (2)	C15—C14—H14A	108.3
C12—N2—C11	107.0 (2)	C22—C14—H14A	108.3
C12—N2—C14	112.1 (2)	C20—C15—C16	117.0 (3)
C11—N2—C14	113.3 (2)	C20—C15—C14	122.4 (3)
C3—C2—C1	117.7 (3)	C16—C15—C14	120.6 (3)
C3—C2—H2A	121.1	C17—C16—C15	121.5 (3)
C1—C2—H2A	121.1	C17—C16—H16A	119.3
C25—O3—C28	117.8 (3)	C15—C16—H16A	119.3
C2—C3—C4	123.5 (4)	C18—C17—C16	120.1 (3)
C2—C3—F	118.5 (4)	C18—C17—H17A	120.0
C4—C3—F	118.0 (4)	C16—C17—H17A	120.0
C3—C4—C5	117.5 (3)	C17—C18—C19	120.1 (3)
C3—C4—H4A	121.3	C17—C18—O2	115.6 (3)
C5—C4—H4A	121.3	C19—C18—O2	124.3 (3)
C4—C5—C6	121.5 (3)	C18—C19—C20	119.1 (3)
C4—C5—H5A	119.3	C18—C19—H19A	120.5
C6—C5—H5A	119.3	C20—C19—H19A	120.5
C1—C6—C5	118.0 (3)	C15—C20—C19	122.3 (3)
C1—C6—C7	122.9 (3)	C15—C20—H20A	118.9
C5—C6—C7	119.1 (3)	C19—C20—H20A	118.9
C8—C7—C6	129.0 (3)	O2—C21—H21A	109.5
C8—C7—H7A	115.5	O2—C21—H21B	109.5
C6—C7—H7A	115.5	H21A—C21—H21B	109.5
C7—C8—C9	122.1 (3)	O2—C21—H21C	109.5
C7—C8—H8A	119.0	H21A—C21—H21C	109.5
C9—C8—H8A	119.0	H21B—C21—H21C	109.5
O1—C9—N1	121.8 (3)	C27—C22—C23	117.2 (3)
O1—C9—C8	119.2 (3)	C27—C22—C14	121.9 (3)
N1—C9—C8	119.0 (3)	C23—C22—C14	120.9 (3)
N1—C10—C11	111.3 (2)	C24—C23—C22	121.3 (3)
N1—C10—H10A	109.4	C24—C23—H23A	119.3
C11—C10—H10A	109.4	C22—C23—H23A	119.3
N1—C10—H10B	109.4	C23—C24—C25	120.9 (3)
C11—C10—H10B	109.4	C23—C24—H24A	119.6
H10A—C10—H10B	108.0	C25—C24—H24A	119.6
N2—C11—C10	110.0 (2)	C26—C25—C24	119.0 (3)
N2—C11—H11A	109.7	C26—C25—O3	125.2 (3)
C10—C11—H11A	109.7	C24—C25—O3	115.8 (3)
N2—C11—H11B	109.7	C25—C26—C27	119.8 (3)
C10—C11—H11B	109.7	C25—C26—H26A	120.1
H11A—C11—H11B	108.2	C27—C26—H26A	120.1
N2—C12—C13	111.2 (3)	C22—C27—C26	121.8 (3)
N2—C12—H12A	109.4	C22—C27—H27A	119.1
C13—C12—H12A	109.4	C26—C27—H27A	119.1
N2—C12—H12B	109.4	O3—C28—H28A	109.5
C13—C12—H12B	109.4	O3—C28—H28B	109.5
H12A—C12—H12B	108.0	H28A—C28—H28B	109.5
N1—C13—C12	111.6 (2)	O3—C28—H28C	109.5
N1—C13—H13A	109.3	H28A—C28—H28C	109.5
C12—C13—H13A	109.3	H28B—C28—H28C	109.5
N1—C13—H13B	109.3

C6—C1—C2—C3	0.4 (5)	N2—C14—C15—C20	−43.6 (4)
C1—C2—C3—C4	−4.6 (6)	C22—C14—C15—C20	79.0 (3)
C1—C2—C3—F	177.5 (3)	N2—C14—C15—C16	138.6 (3)
C2—C3—C4—C5	4.9 (6)	C22—C14—C15—C16	−98.9 (3)
F—C3—C4—C5	−177.2 (3)	C20—C15—C16—C17	0.7 (4)
C3—C4—C5—C6	−1.0 (5)	C14—C15—C16—C17	178.7 (3)
C2—C1—C6—C5	3.1 (5)	C15—C16—C17—C18	−0.4 (4)
C2—C1—C6—C7	−176.5 (3)	C16—C17—C18—C19	−0.1 (4)
C4—C5—C6—C1	−2.8 (5)	C16—C17—C18—O2	179.6 (2)
C4—C5—C6—C7	176.9 (3)	C21—O2—C18—C17	174.3 (3)
C1—C6—C7—C8	15.0 (5)	C21—O2—C18—C19	−5.9 (4)
C5—C6—C7—C8	−164.7 (3)	C17—C18—C19—C20	0.2 (4)
C6—C7—C8—C9	178.1 (3)	O2—C18—C19—C20	−179.5 (3)
C10—N1—C9—O1	−9.2 (4)	C16—C15—C20—C19	−0.6 (4)
C13—N1—C9—O1	179.7 (3)	C14—C15—C20—C19	−178.6 (3)
C10—N1—C9—C8	171.6 (3)	C18—C19—C20—C15	0.2 (4)
C13—N1—C9—C8	0.6 (5)	N2—C14—C22—C27	−128.0 (3)
C7—C8—C9—O1	−7.7 (5)	C15—C14—C22—C27	109.0 (3)
C7—C8—C9—N1	171.5 (3)	N2—C14—C22—C23	53.2 (4)
C9—N1—C10—C11	137.5 (3)	C15—C14—C22—C23	−69.8 (3)
C13—N1—C10—C11	−50.3 (4)	C27—C22—C23—C24	0.0 (5)
C12—N2—C11—C10	−63.1 (3)	C14—C22—C23—C24	178.9 (3)
C14—N2—C11—C10	172.9 (2)	C22—C23—C24—C25	−0.7 (5)
N1—C10—C11—N2	57.9 (3)	C23—C24—C25—C26	1.4 (5)
C11—N2—C12—C13	62.0 (3)	C23—C24—C25—O3	−179.1 (3)
C14—N2—C12—C13	−173.2 (2)	C28—O3—C25—C26	9.6 (4)
C9—N1—C13—C12	−139.8 (3)	C28—O3—C25—C24	−169.8 (3)
C10—N1—C13—C12	48.7 (4)	C24—C25—C26—C27	−1.4 (4)
N2—C12—C13—N1	−55.2 (4)	O3—C25—C26—C27	179.2 (3)
C12—N2—C14—C15	−176.8 (2)	C23—C22—C27—C26	0.0 (4)
C11—N2—C14—C15	−55.6 (3)	C14—C22—C27—C26	−178.9 (3)
C12—N2—C14—C22	60.3 (3)	C25—C26—C27—C22	0.7 (5)
C11—N2—C14—C22	−178.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1ⁱ	0.93	2.28	3.131 (4)	152
C17—H17A···O3ⁱⁱ	0.93	2.60	3.499 (4)	163
C10—H10A···O1	0.97	2.30	2.715 (4)	105
C7—H7A···O1	0.93	2.43	2.786 (4)	102

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

Experimental details

Crystal data
Chemical formula	C₂₈H₂₉FN₂O₃
M_r	460.53
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.235 (2), 7.8420 (16), 30.385 (6)
β (°)	96.65 (3)
V (Å³)	2422.4 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	Multi-scan ψ scan
T_min, T_max	0.983, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	4730, 4463, 2366
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.170, 1.01
No. of reflections	4463
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.18

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), 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	2.28	3.131 (4)	152
C17—H17A···O3ⁱⁱ	0.93	2.60	3.499 (4)	163
C10—H10A···O1	0.97	2.30	2.715 (4)	105
C7—H7A···O1	0.93	2.43	2.786 (4)	102

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

Acknowledgements

This study was supported financially by grant No. BK2010538 from the Natural Science Foundation of Jiangsu Province. The authors extend special thanks to Professor Hua-Qin Wang of the Analysis Centre, Nanjing University, for the data collection.

References

Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Mouillé, Y., Cotrait, M., Hospital, M. & Marsau, P. (1975). Acta Cryst. B31, 1495–1496. CSD CrossRef IUCr Journals Web of Science 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
Point, D., Coudert, P., Leal, F., Rubat, C., Sautou-Miranda, V., Chopineau, J. & Couquelet, J. (1998). Farmaco, 53, 85–88. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, Y., Chen, Q.-X., Wang, Q., Song, K.-K. & Qiu, L. (2005). Food Chem. 92, 707–712. CrossRef CAS Google Scholar
Wu, B., Zhou, L. & Cai, H.-H. (2008). Chin. Chem. Lett. 19, 1163–1166. Web of Science CrossRef CAS Google Scholar

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Volume 67| Part 3| March 2011| Page o697

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

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