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

In the title compound, C(28)H(29)FN(2)O(3), the conformation about the ethene bond is E. The piperazine ring adopts a chair conformation. In the crystal, mol-ecules are linked by inter-molecular 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 = 460.53

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.170

S = 1.01

4463 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.18 e Å−3

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.

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

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

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

C28H29FN2O3	F(000) = 976
Mr = 460.53	Dx = 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

Enraf–Nonius CAD-4 diffractometer	2366 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
graphite	θmax = 25.4°, θmin = 1.4°
ω and 2θ scans	h = 0→12
Absorption correction: multi-scan ψ scan	k = 0→9
Tmin = 0.983, Tmax = 0.991	l = −36→36
4730 measured reflections	3 standard reflections every 200 reflections
4463 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.080P)2] where P = (Fo2 + 2Fc2)/3
4463 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .