(E)-1-(4-Benzhydrylpiperazin-1-yl)-3-(2-eth-oxy-phen-yl)prop-2-en-1-one.

In the title mol-ecule, C(28)H(30)N(2)O(2), the piperazine ring adopts a chair conformation and the C=C bond exhibits an E conformation. The dihedral angle between the terminal phenyl rings is 71.4 (2). In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming [010] chains.

Related literature

For properties of cinnamic acid derivatives, see: Shi et al. (2005 ▶); Qian et al. (2010 ▶). For the synthesis, see: Wu et al. (2008 ▶). For related structures, see: Mouillé et al. (1975) ▶; Zhong et al. (2011 ▶).

Experimental

Crystal data

C28H30N2O2

M = 426.54

Monoclinic,

a = 11.858 (2) Å

b = 12.786 (3) Å

c = 16.044 (3) Å

β = 94.63 (3)°

V = 2424.6 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

4673 measured reflections

4446 independent reflections

2022 reflections with I > 2σ(I)

R int = 0.063

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.155

S = 1.00

4446 reflections

265 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.22 e Å−3

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: SHELXL97 (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811045922/hb6487sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045922/hb6487Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045922/hb6487Isup3.cml

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

C28H30N2O2	F(000) = 912
Mr = 426.54	Dx = 1.169 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 11.858 (2) Å	θ = 9–12°
b = 12.786 (3) Å	µ = 0.07 mm−1
c = 16.044 (3) Å	T = 293 K
β = 94.63 (3)°	Block, pale-yellow
V = 2424.6 (8) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	Rint = 0.063
Radiation source: fine-focus sealed tube	θmax = 25.4°, θmin = 2.0°
graphite	h = 0→14
ω/2θ scans	k = 0→15
4673 measured reflections	l = −19→19
4446 independent reflections	3 standard reflections every 200 reflections
2022 reflections with I > 2σ(I)	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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.030P)2 + 1.550P] where P = (Fo2 + 2Fc2)/3
4446 reflections	(Δ/σ)max < 0.001
265 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.22 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
O1	0.2436 (2)	0.32431 (17)	0.49193 (13)	0.0823 (8)
N1	0.2112 (2)	0.69070 (19)	0.57757 (17)	0.0641 (7)
C1	0.0062 (5)	0.7832 (3)	0.6573 (3)	0.1159 (15)
H1A	−0.0014	0.7739	0.5996	0.139*
C2	−0.0941 (4)	0.7913 (3)	0.6932 (3)	0.103
H2A	−0.1671	0.7873	0.6674	0.124*
C3	−0.0616 (5)	0.8068 (3)	0.7764 (3)	0.1158 (15)
H3A	−0.1233	0.8218	0.8067	0.139*
C4	0.0365 (5)	0.8061 (4)	0.8263 (3)	0.1107 (15)
H4A	0.0396	0.8135	0.8841	0.133*
C5	0.1251 (5)	0.7940 (3)	0.7854 (4)	0.1213 (16)
H5A	0.1962	0.7901	0.8142	0.146*
C6	0.1140 (4)	0.7863 (3)	0.6906 (4)	0.1098 (17)
O2	0.3846 (2)	0.12578 (18)	0.28272 (15)	0.0852 (8)
N2	0.2698 (3)	0.4974 (2)	0.50411 (17)	0.0790 (9)
C7	0.2064 (3)	0.7757 (3)	0.6338 (3)	0.095
H7A	0.2752	0.7684	0.6715	0.114*
C8	0.2259 (4)	0.8738 (3)	0.5848 (3)	0.1061 (14)
C9	0.3187 (3)	0.9292 (3)	0.6198 (2)	0.084
H9A	0.3618	0.9034	0.6663	0.100*
C10	0.3444 (4)	1.0185 (3)	0.5861 (3)	0.097
H10A	0.4150	1.0458	0.6040	0.117*
C11	0.2883 (5)	1.0710 (4)	0.5344 (3)	0.1141 (15)
H11A	0.3101	1.1387	0.5221	0.137*
C12	0.1862 (5)	1.0252 (5)	0.4921 (3)	0.1197 (17)
H12A	0.1442	1.0597	0.4490	0.144*
C13	0.1550 (4)	0.9251 (5)	0.5206 (3)	0.1267 (17)
H13A	0.0891	0.8930	0.4979	0.152*
C14	0.2828 (3)	0.6824 (3)	0.5164 (3)	0.1075 (15)
H14A	0.3513	0.7181	0.5377	0.129*
H14B	0.2498	0.7249	0.4707	0.129*
C15	0.3189 (4)	0.5913 (3)	0.4794 (3)	0.1085 (15)
H15A	0.4002	0.5859	0.4912	0.130*
H15B	0.3041	0.5981	0.4193	0.130*
C16	0.1949 (4)	0.4975 (3)	0.5695 (3)	0.1160 (16)
H16A	0.1277	0.4580	0.5508	0.139*
H16B	0.2315	0.4614	0.6175	0.139*
C17	0.1613 (4)	0.5974 (3)	0.5953 (3)	0.1131 (16)
H17A	0.0823	0.6043	0.5749	0.136*
H17B	0.1627	0.5941	0.6557	0.136*
C18	0.2861 (3)	0.4023 (3)	0.4683 (2)	0.0757 (11)
C19	0.3575 (3)	0.4008 (2)	0.39672 (19)	0.0670 (9)
H19A	0.3894	0.4628	0.3797	0.080*
C20	0.3765 (3)	0.3152 (2)	0.35741 (18)	0.0720 (10)
H20A	0.3453	0.2550	0.3786	0.086*
C21	0.4405 (3)	0.3001 (3)	0.28366 (19)	0.0637 (9)
C22	0.4967 (3)	0.3810 (3)	0.2482 (2)	0.0733 (10)
H22A	0.4923	0.4476	0.2711	0.088*
C23	0.5596 (3)	0.3673 (3)	0.1799 (2)	0.0918 (13)
H23A	0.5981	0.4232	0.1584	0.110*
C24	0.5641 (3)	0.2701 (3)	0.1446 (2)	0.0873 (12)
H24A	0.6081	0.2590	0.1000	0.105*
C25	0.5004 (3)	0.1846 (3)	0.1769 (2)	0.0829 (11)
H25A	0.4989	0.1199	0.1504	0.100*
C26	0.4417 (3)	0.1990 (3)	0.2469 (2)	0.0721 (10)
C27	0.3835 (3)	0.0218 (3)	0.2493 (2)	0.0919 (12)
H27A	0.4600	−0.0052	0.2505	0.110*
H27B	0.3516	0.0223	0.1917	0.110*
C28	0.3142 (3)	−0.0455 (3)	0.3005 (3)	0.1021 (13)
H28A	0.3140	−0.1158	0.2794	0.153*
H28B	0.2381	−0.0194	0.2977	0.153*
H28C	0.3457	−0.0449	0.3575	0.153*

	U11	U22	U33	U12	U13	U23
O1	0.129 (2)	0.0544 (14)	0.0689 (15)	−0.0102 (14)	0.0430 (14)	−0.0047 (12)
N1	0.0595 (18)	0.0530 (16)	0.0809 (19)	0.0014 (14)	0.0131 (15)	−0.0082 (15)
C1	0.119 (4)	0.121 (4)	0.111 (4)	−0.025 (3)	0.028 (3)	0.009 (3)
C2	0.103	0.103	0.103	0.000	0.008	0.000
C3	0.128 (4)	0.102 (3)	0.120 (4)	0.010 (3)	0.024 (3)	−0.005 (3)
C4	0.114 (4)	0.110 (4)	0.110 (4)	0.029 (3)	0.024 (3)	−0.014 (3)
C5	0.112 (4)	0.097 (3)	0.153 (5)	0.016 (3)	0.003 (4)	−0.006 (3)
C6	0.102 (4)	0.077 (3)	0.162 (5)	0.004 (3)	0.080 (4)	−0.032 (3)
O2	0.104 (2)	0.0662 (15)	0.0907 (18)	0.0147 (14)	0.0390 (15)	−0.0212 (14)
N2	0.113 (2)	0.0495 (16)	0.081 (2)	−0.0052 (16)	0.0478 (18)	−0.0007 (15)
C7	0.095	0.095	0.095	0.000	0.008	0.000
C8	0.107 (4)	0.090 (3)	0.125 (4)	−0.007 (3)	0.032 (3)	−0.010 (3)
C9	0.084	0.084	0.084	0.000	0.007	0.000
C10	0.097	0.097	0.097	0.000	0.008	0.000
C11	0.137 (4)	0.088 (3)	0.120 (4)	0.009 (3)	0.029 (3)	0.013 (3)
C12	0.124 (5)	0.146 (5)	0.090 (3)	0.046 (4)	0.011 (3)	−0.005 (4)
C13	0.113 (4)	0.154 (5)	0.114 (4)	−0.005 (4)	0.019 (3)	−0.032 (4)
C14	0.104 (3)	0.066 (2)	0.162 (4)	−0.023 (2)	0.068 (3)	−0.001 (3)
C15	0.153 (4)	0.074 (3)	0.108 (3)	−0.016 (3)	0.067 (3)	−0.019 (3)
C16	0.171 (4)	0.079 (3)	0.110 (3)	−0.009 (3)	0.085 (3)	−0.013 (2)
C17	0.136 (4)	0.072 (3)	0.143 (4)	−0.006 (3)	0.088 (3)	−0.010 (3)
C18	0.098 (3)	0.059 (2)	0.076 (2)	0.006 (2)	0.047 (2)	−0.0040 (19)
C19	0.084 (2)	0.0472 (18)	0.075 (2)	0.0158 (17)	0.0369 (19)	0.0063 (17)
C20	0.114 (3)	0.0499 (19)	0.057 (2)	0.0050 (19)	0.039 (2)	0.0019 (16)
C21	0.064 (2)	0.068 (2)	0.061 (2)	0.0222 (18)	0.0102 (17)	0.0044 (18)
C22	0.094 (3)	0.063 (2)	0.066 (2)	0.023 (2)	0.024 (2)	0.0038 (18)
C23	0.137 (4)	0.080 (3)	0.065 (2)	0.000 (3)	0.046 (2)	0.007 (2)
C24	0.090 (3)	0.112 (3)	0.065 (2)	0.012 (3)	0.034 (2)	0.005 (2)
C25	0.070 (2)	0.101 (3)	0.082 (3)	0.024 (2)	0.030 (2)	−0.011 (2)
C26	0.074 (3)	0.075 (2)	0.069 (2)	0.016 (2)	0.013 (2)	0.003 (2)
C27	0.097 (3)	0.093 (3)	0.087 (3)	0.018 (2)	0.014 (2)	−0.037 (2)
C28	0.097 (3)	0.083 (3)	0.129 (4)	0.014 (2)	0.027 (3)	−0.017 (3)

O1—C18	1.194 (4)	C13—H13A	0.9300
N1—C14	1.352 (4)	C14—C15	1.391 (4)
N1—C17	1.372 (4)	C14—H14A	0.9700
N1—C7	1.416 (4)	C14—H14B	0.9700
C1—C6	1.347 (6)	C15—H15A	0.9700
C1—C2	1.367 (6)	C15—H15B	0.9700
C1—H1A	0.9300	C16—C17	1.410 (5)
C2—C3	1.373 (6)	C16—H16A	0.9700
C2—H2A	0.9300	C16—H16B	0.9700
C3—C4	1.357 (6)	C17—H17A	0.9700
C3—H3A	0.9300	C17—H17B	0.9700
C4—C5	1.292 (6)	C18—C19	1.480 (4)
C4—H4A	0.9300	C19—C20	1.291 (4)
C5—C6	1.519 (6)	C19—H19A	0.9300
C5—H5A	0.9300	C20—C21	1.470 (4)
C6—C7	1.487 (5)	C20—H20A	0.9300
O2—C26	1.315 (4)	C21—C22	1.378 (4)
O2—C27	1.434 (4)	C21—C26	1.421 (4)
N2—C18	1.366 (4)	C22—C23	1.385 (4)
N2—C15	1.405 (4)	C22—H22A	0.9300
N2—C16	1.428 (4)	C23—C24	1.368 (5)
C7—C8	1.508 (6)	C23—H23A	0.9300
C7—H7A	0.9800	C24—C25	1.449 (5)
C8—C9	1.389 (5)	C24—H24A	0.9300
C8—C13	1.435 (6)	C25—C26	1.380 (4)
C9—C10	1.310 (5)	C25—H25A	0.9300
C9—H9A	0.9300	C27—C28	1.482 (5)
C10—C11	1.222 (5)	C27—H27A	0.9700
C10—H10A	0.9300	C27—H27B	0.9700
C11—C12	1.461 (6)	C28—H28A	0.9600
C11—H11A	0.9300	C28—H28B	0.9600
C12—C13	1.419 (6)	C28—H28C	0.9600
C12—H12A	0.9300
C14—N1—C17	112.8 (3)	C14—C15—H15A	108.2
C14—N1—C7	125.6 (3)	N2—C15—H15A	108.2
C17—N1—C7	119.7 (3)	C14—C15—H15B	108.2
C6—C1—C2	131.4 (5)	N2—C15—H15B	108.2
C6—C1—H1A	114.3	H15A—C15—H15B	107.3
C2—C1—H1A	114.3	C17—C16—N2	115.1 (3)
C1—C2—C3	103.6 (4)	C17—C16—H16A	108.5
C1—C2—H2A	128.2	N2—C16—H16A	108.5
C3—C2—H2A	128.2	C17—C16—H16B	108.5
C4—C3—C2	137.0 (5)	N2—C16—H16B	108.5
C4—C3—H3A	111.5	H16A—C16—H16B	107.5
C2—C3—H3A	111.5	N1—C17—C16	126.2 (3)
C5—C4—C3	113.3 (5)	N1—C17—H17A	105.8
C5—C4—H4A	123.4	C16—C17—H17A	105.8
C3—C4—H4A	123.4	N1—C17—H17B	105.8
C4—C5—C6	120.5 (5)	C16—C17—H17B	105.8
C4—C5—H5A	119.7	H17A—C17—H17B	106.2
C6—C5—H5A	119.7	O1—C18—N2	122.2 (3)
C1—C6—C7	118.5 (5)	O1—C18—C19	121.2 (3)
C1—C6—C5	113.7 (4)	N2—C18—C19	116.6 (3)
C7—C6—C5	127.7 (5)	C20—C19—C18	121.6 (3)
C26—O2—C27	119.1 (3)	C20—C19—H19A	119.2
C18—N2—C15	124.4 (3)	C18—C19—H19A	119.2
C18—N2—C16	115.3 (3)	C19—C20—C21	128.8 (3)
C15—N2—C16	120.2 (3)	C19—C20—H20A	115.6
N1—C7—C6	122.0 (4)	C21—C20—H20A	115.6
N1—C7—C8	106.9 (3)	C22—C21—C26	119.4 (3)
C6—C7—C8	113.3 (4)	C22—C21—C20	122.1 (3)
N1—C7—H7A	104.3	C26—C21—C20	118.5 (3)
C6—C7—H7A	104.3	C21—C22—C23	122.7 (3)
C8—C7—H7A	104.3	C21—C22—H22A	118.7
C9—C8—C13	117.2 (4)	C23—C22—H22A	118.7
C9—C8—C7	111.3 (5)	C24—C23—C22	119.0 (3)
C13—C8—C7	130.4 (5)	C24—C23—H23A	120.5
C10—C9—C8	118.7 (4)	C22—C23—H23A	120.5
C10—C9—H9A	120.6	C23—C24—C25	119.9 (3)
C8—C9—H9A	120.6	C23—C24—H24A	120.1
C11—C10—C9	128.8 (5)	C25—C24—H24A	120.1
C11—C10—H10A	115.6	C26—C25—C24	120.1 (3)
C9—C10—H10A	115.6	C26—C25—H25A	119.9
C10—C11—C12	118.8 (5)	C24—C25—H25A	119.9
C10—C11—H11A	120.6	O2—C26—C25	124.9 (3)
C12—C11—H11A	120.6	O2—C26—C21	116.3 (3)
C13—C12—C11	116.0 (5)	C25—C26—C21	118.8 (3)
C13—C12—H12A	122.0	O2—C27—C28	108.6 (3)
C11—C12—H12A	122.0	O2—C27—H27A	110.0
C12—C13—C8	119.4 (5)	C28—C27—H27A	110.0
C12—C13—H13A	120.3	O2—C27—H27B	110.0
C8—C13—H13A	120.3	C28—C27—H27B	110.0
N1—C14—C15	127.5 (3)	H27A—C27—H27B	108.3
N1—C14—H14A	105.4	C27—C28—H28A	109.5
C15—C14—H14A	105.4	C27—C28—H28B	109.5
N1—C14—H14B	105.4	H28A—C28—H28B	109.5
C15—C14—H14B	105.4	C27—C28—H28C	109.5
H14A—C14—H14B	106.0	H28A—C28—H28C	109.5
C14—C15—N2	116.4 (3)	H28B—C28—H28C	109.5
C6—C1—C2—C3	1.4 (7)	C18—N2—C15—C14	172.9 (4)
C1—C2—C3—C4	−7.1 (8)	C16—N2—C15—C14	−5.5 (6)
C2—C3—C4—C5	5.4 (9)	C18—N2—C16—C17	−168.4 (4)
C3—C4—C5—C6	2.2 (7)	C15—N2—C16—C17	10.1 (6)
C2—C1—C6—C7	−179.6 (4)	C14—N1—C17—C16	13.8 (7)
C2—C1—C6—C5	4.0 (8)	C7—N1—C17—C16	−151.5 (5)
C4—C5—C6—C1	−5.9 (7)	N2—C16—C17—N1	−15.2 (8)
C4—C5—C6—C7	178.0 (4)	C15—N2—C18—O1	179.2 (4)
C14—N1—C7—C6	170.6 (4)	C16—N2—C18—O1	−2.4 (6)
C17—N1—C7—C6	−26.1 (6)	C15—N2—C18—C19	−2.2 (6)
C14—N1—C7—C8	38.0 (5)	C16—N2—C18—C19	176.2 (3)
C17—N1—C7—C8	−158.7 (4)	O1—C18—C19—C20	−0.1 (6)
C1—C6—C7—N1	−53.6 (6)	N2—C18—C19—C20	−178.7 (4)
C5—C6—C7—N1	122.3 (5)	C18—C19—C20—C21	177.2 (3)
C1—C6—C7—C8	76.4 (5)	C19—C20—C21—C22	3.7 (6)
C5—C6—C7—C8	−107.7 (5)	C19—C20—C21—C26	−174.7 (4)
N1—C7—C8—C9	−122.0 (4)	C26—C21—C22—C23	−3.2 (5)
C6—C7—C8—C9	100.8 (5)	C20—C21—C22—C23	178.5 (3)
N1—C7—C8—C13	70.4 (6)	C21—C22—C23—C24	1.7 (6)
C6—C7—C8—C13	−66.7 (6)	C22—C23—C24—C25	2.3 (6)
C13—C8—C9—C10	−8.2 (6)	C23—C24—C25—C26	−4.7 (6)
C7—C8—C9—C10	−177.6 (3)	C27—O2—C26—C25	1.5 (5)
C8—C9—C10—C11	12.5 (7)	C27—O2—C26—C21	−179.3 (3)
C9—C10—C11—C12	−10.9 (7)	C24—C25—C26—O2	−177.6 (3)
C10—C11—C12—C13	5.5 (7)	C24—C25—C26—C21	3.2 (5)
C11—C12—C13—C8	−2.8 (6)	C22—C21—C26—O2	−178.7 (3)
C9—C8—C13—C12	4.3 (6)	C20—C21—C26—O2	−0.2 (5)
C7—C8—C13—C12	171.3 (4)	C22—C21—C26—C25	0.6 (5)
C17—N1—C14—C15	−8.2 (7)	C20—C21—C26—C25	179.1 (3)
C7—N1—C14—C15	156.1 (5)	C26—O2—C27—C28	179.8 (3)
N1—C14—C15—N2	4.7 (8)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1i	0.93	2.54	3.343 (6)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O1i	0.93	2.54	3.343 (6)	146

Symmetry code: (i) .