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

Zhong, Y.; Zhang, X.P.; Wu, B.

doi:10.1107/S1600536811055796

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o298

doi:10.1107/S1600536811055796

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

Yan Zhong,^a XiaoPing Zhang ^b and Bin Wu ^c ^*

^aSchool of Chemistry and Chemical Engineering, Southeast University, Sipailou No. 2 Nanjing, Nanjing 210096, People's Republic of China, ^bCentre of Laboratory Animals, Nanjing medical University, Hanzhong Road No. 140 Nanjing, Nanjing 210029, People's Republic of China, and ^cSchool 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 24 December 2011; accepted 26 December 2011; online 7 January 2012)

The asymmetric unit of the title compound, C₃₂H₃₈N₂O₅·2C₂H₆O, contains one main molecule and two solvent molecules, which interact via intermolecular O—H⋯O hydrogen bonds. The piperazine ring adopts a chair conformation. The crystal packing exhibits weak intermolecular C—H⋯O hydrogen bonds and voids of 31 Å³.

Related literature

For the crystal structures of related cinnamic acid derivatives, see: Teng et al. (2011 ); Zhong & Wu (2011 ). For further synthetic details, see: Wu et al. (2008 ).

Experimental

Crystal data

C₃₂H₃₈N₂O₅·2C₂H₆O
M_r = 622.78
Triclinic, $[P \overline 1]$
a = 12.511 (3) Å
b = 12.564 (3) Å
c = 13.601 (3) Å
α = 88.13 (3)°
β = 70.62 (3)°
γ = 65.84 (3)°
V = 1826.9 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.977, T_max = 0.992
6687 measured reflections
6687 independent reflections
2904 reflections with I > 2σ(I)
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.166
S = 1.00
6687 reflections
412 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O3	0.82	1.97	2.699 (4)	147
O7—H7C⋯O6	0.82	1.91	2.730 (6)	178
C14—H14A⋯O7ⁱ	0.97	2.54	3.436 (7)	153
C32—H32A⋯O4ⁱⁱ	0.96	2.57	3.258 (6)	129
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y, z.

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/S1600536811055796/cv5226sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055796/cv5226Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811055796/cv5226Isup3.cml

checkCIF report

Comment top

As a continuation of our study of cinnamic acid derivatives (Teng et al., 2011; Zhong et al., 2011), 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., 2011). The molecule of (I) exists an E configulation with respect to the C11=C12 ethene bond [1.306 (4)]. The piperazine ring adopts a chair conformation. In the crystal structure, the molecules are linked by intermolecular C—H···O and O—H···O hydrogen bonds (Table 1).

Related literature top

For the crystal structures of related cinnamic acid derivatives, see: Teng et al. (2011); Zhong & Wu (2011). 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-(3,4-diethoxyphenyl)acrylic acid (0.945 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-(bis(4-methoxyphenyl)methyl)iperazine (1.874 g; 6 mmol) in the presence of triethylamine (5 ml) for 12 h at room temperature. The resultant mixture was cooled. The solid, (E)-1-(4-(bis(4-methoxyphenyl)methyl)piperazin-1-yl) -3-(3,4-diethoxyphenyl)prop-2-en-1-one obtained was filtered and was recrystallized from ethanol. The pale-yellow single crystals of the title compound used in x-ray diffraction studies were grown in ethyl acetate: hexane (2:1) 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 content of asymmetric part of the title compound showing the atomic numbering and 30% probability displacement ellipsoids. H atoms not involved in hydrogen-bonding (dashed lines) omitted for clarity.

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

Crystal data top

C₃₂H₃₈N₂O₅·2C₂H₆O	Z = 2
M_r = 622.78	F(000) = 672
Triclinic, P1	D_x = 1.132 Mg m⁻³
a = 12.511 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.564 (3) Å	Cell parameters from 25 reflections
c = 13.601 (3) Å	θ = 10–13°
α = 88.13 (3)°	µ = 0.08 mm⁻¹
β = 70.62 (3)°	T = 293 K
γ = 65.84 (3)°	Block, pale-yellow
V = 1826.9 (6) Å³	0.30 × 0.10 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2904 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 25.4°, θ_min = 1.6°
ω/2θ scans	h = −13→15
Absorption correction: ψ scan (North et al., 1968)	k = −15→15
T_min = 0.977, T_max = 0.992	l = 0→16
6687 measured reflections	3 standard reflections every 200 reflections
6687 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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.166	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.064P)²] where P = (F_o² + 2F_c²)/3
6687 reflections	(Δ/σ)_max < 0.001
412 parameters	Δρ_max = 0.19 e Å⁻³
2 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₃₂H₃₈N₂O₅·2C₂H₆O	γ = 65.84 (3)°
M_r = 622.78	V = 1826.9 (6) Å³
Triclinic, P1	Z = 2
a = 12.511 (3) Å	Mo Kα radiation
b = 12.564 (3) Å	µ = 0.08 mm⁻¹
c = 13.601 (3) Å	T = 293 K
α = 88.13 (3)°	0.30 × 0.10 × 0.10 mm
β = 70.62 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2904 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.000
T_min = 0.977, T_max = 0.992	3 standard reflections every 200 reflections
6687 measured reflections	intensity decay: 1%
6687 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	2 restraints
wR(F²) = 0.166	H-atom parameters constrained
S = 1.00	Δρ_max = 0.19 e Å⁻³
6687 reflections	Δρ_min = −0.16 e Å⁻³
412 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	0.7645 (2)	0.43579 (19)	0.73201 (16)	0.0748 (7)
N1	0.3880 (2)	0.3238 (2)	0.4502 (2)	0.0679 (7)
C1	0.6388 (3)	0.4767 (3)	0.7589 (2)	0.0600 (8)
O2	0.6341 (2)	0.58409 (19)	0.90097 (16)	0.0763 (7)
N2	0.4710 (2)	0.1072 (2)	0.32428 (18)	0.0589 (7)
C2	0.5791 (3)	0.4492 (3)	0.7042 (2)	0.0604 (9)
H2A	0.6264	0.3976	0.6426	0.073*
O3	0.2255 (2)	0.4493 (2)	0.58302 (18)	0.0793 (7)
C3	0.4490 (3)	0.4953 (3)	0.7369 (2)	0.0620 (9)
O4	1.0072 (2)	−0.2941 (2)	0.0568 (2)	0.0970 (8)
C4	0.3823 (3)	0.5725 (3)	0.8292 (2)	0.0747 (10)
H4A	0.2954	0.6051	0.8532	0.090*
O5	0.2255 (3)	−0.0921 (2)	0.0774 (2)	0.1021 (9)
C5	0.4408 (3)	0.6019 (3)	0.8857 (2)	0.0757 (10)
H5A	0.3933	0.6527	0.9477	0.091*
C6	0.5677 (3)	0.5574 (3)	0.8519 (2)	0.0652 (9)
C7	0.5645 (3)	0.6754 (3)	0.9877 (2)	0.0774 (11)
H7A	0.5113	0.6515	1.0447	0.093*
H7B	0.5119	0.7464	0.9663	0.093*
C8	0.6542 (3)	0.6980 (3)	1.0227 (3)	0.0998 (13)
H8A	0.6094	0.7638	1.0766	0.150*
H8B	0.7109	0.7152	0.9643	0.150*
H8C	0.7003	0.6298	1.0500	0.150*
C9	0.8405 (3)	0.3706 (3)	0.6294 (2)	0.0761 (10)
H9A	0.8141	0.4160	0.5760	0.091*
H9B	0.8323	0.2975	0.6254	0.091*
C10	0.9728 (3)	0.3462 (4)	0.6129 (3)	0.1238 (17)
H10A	1.0259	0.3027	0.5450	0.186*
H10B	0.9979	0.3011	0.6661	0.186*
H10C	0.9798	0.4191	0.6169	0.186*
C11	0.3817 (3)	0.4704 (3)	0.6783 (2)	0.0689 (9)
H11A	0.2956	0.5000	0.7119	0.083*
C12	0.4248 (3)	0.4126 (3)	0.5852 (2)	0.0629 (9)
H12A	0.5102	0.3808	0.5474	0.076*
C13	0.3408 (4)	0.3975 (3)	0.5399 (3)	0.0627 (9)
C14	0.5202 (3)	0.2540 (3)	0.3899 (3)	0.0734 (10)
H14A	0.5711	0.2641	0.4261	0.088*
H14B	0.5415	0.2812	0.3216	0.088*
C15	0.5478 (3)	0.1252 (3)	0.3761 (2)	0.0661 (9)
H15A	0.6354	0.0804	0.3346	0.079*
H15B	0.5318	0.0967	0.4442	0.079*
C16	0.3399 (3)	0.1738 (3)	0.3898 (2)	0.0673 (9)
H16A	0.3243	0.1451	0.4578	0.081*
H16B	0.2868	0.1618	0.3572	0.081*
C17	0.3071 (3)	0.3040 (3)	0.4043 (3)	0.0696 (9)
H17A	0.3165	0.3343	0.3369	0.084*
H17B	0.2206	0.3458	0.4498	0.084*
C18	0.5014 (3)	−0.0179 (3)	0.3039 (2)	0.0615 (9)
H18A	0.4825	−0.0482	0.3719	0.074*
C19	0.6393 (3)	−0.0892 (3)	0.2416 (2)	0.0572 (8)
C20	0.7021 (3)	−0.0505 (3)	0.1564 (2)	0.0639 (9)
H20A	0.6619	0.0237	0.1384	0.077*
C21	0.8259 (3)	−0.1216 (3)	0.0964 (3)	0.0719 (10)
H21A	0.8682	−0.0942	0.0391	0.086*
C22	0.8859 (4)	−0.2317 (3)	0.1212 (3)	0.0714 (10)
C23	0.8234 (4)	−0.2700 (3)	0.2074 (3)	0.0784 (10)
H23A	0.8638	−0.3439	0.2258	0.094*
C24	0.7014 (4)	−0.1997 (3)	0.2664 (3)	0.0726 (10)
H24A	0.6598	−0.2270	0.3243	0.087*
C25	1.0723 (4)	−0.4088 (4)	0.0787 (3)	0.1177 (15)
H25A	1.1550	−0.4439	0.0271	0.177*
H25B	1.0284	−0.4555	0.0768	0.177*
H25C	1.0778	−0.4048	0.1471	0.177*
C26	0.4215 (3)	−0.0353 (3)	0.2477 (2)	0.0575 (8)
C27	0.3708 (3)	−0.1137 (3)	0.2767 (3)	0.0730 (10)
H27A	0.3807	−0.1537	0.3341	0.088*
C28	0.3052 (3)	−0.1346 (3)	0.2223 (3)	0.0828 (11)
H28A	0.2718	−0.1892	0.2426	0.099*
C29	0.2886 (3)	−0.0757 (3)	0.1386 (3)	0.0689 (9)
C30	0.3385 (3)	0.0033 (3)	0.1085 (3)	0.0718 (10)
H30A	0.3272	0.0436	0.0516	0.086*
C31	0.4052 (3)	0.0238 (3)	0.1617 (2)	0.0660 (9)
H31A	0.4397	0.0773	0.1403	0.079*
C32	0.1610 (4)	−0.1626 (4)	0.1114 (3)	0.1240 (16)
H32A	0.1211	−0.1660	0.0630	0.186*
H32B	0.0990	−0.1298	0.1798	0.186*
H32C	0.2188	−0.2405	0.1148	0.186*
O6	0.0879 (4)	0.6828 (3)	0.6384 (3)	0.1925 (19)
H6A	0.1356	0.6162	0.6429	0.289*
C33	−0.0052 (9)	0.6966 (9)	0.8023 (7)	0.307 (6)
H33A	−0.0769	0.7214	0.8657	0.461*
H33B	0.0398	0.7435	0.7999	0.461*
H33C	0.0483	0.6155	0.8007	0.461*
C34	−0.0443 (9)	0.7107 (8)	0.7151 (8)	0.283 (6)
H34C	−0.1044	0.7900	0.7156	0.340*
H34D	−0.0751	0.6540	0.7052	0.340*
O7	0.2275 (4)	0.7986 (4)	0.5355 (3)	0.1730 (16)
H7C	0.1836	0.7656	0.5666	0.259*
C36	0.1491 (9)	0.9230 (10)	0.5390 (7)	0.310 (6)
H36A	0.1965	0.9620	0.4943	0.372*
H36B	0.0786	0.9342	0.5180	0.372*
C35	0.1096 (9)	0.9642 (10)	0.6458 (9)	0.406 (9)
H35A	0.1206	1.0347	0.6516	0.609*
H35B	0.1583	0.9054	0.6794	0.609*
H35C	0.0229	0.9806	0.6792	0.609*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0722 (16)	0.0763 (16)	0.0590 (14)	−0.0177 (13)	−0.0172 (12)	−0.0220 (12)
N1	0.0720 (19)	0.0664 (18)	0.0625 (17)	−0.0264 (16)	−0.0218 (15)	−0.0141 (14)
C1	0.072 (2)	0.051 (2)	0.0495 (19)	−0.0178 (18)	−0.0207 (18)	−0.0059 (15)
O2	0.0844 (16)	0.0748 (16)	0.0606 (14)	−0.0240 (13)	−0.0236 (12)	−0.0231 (12)
N2	0.0703 (18)	0.0586 (17)	0.0517 (15)	−0.0273 (14)	−0.0253 (14)	−0.0014 (13)
C2	0.072 (2)	0.058 (2)	0.0466 (18)	−0.0269 (18)	−0.0147 (17)	−0.0075 (15)
O3	0.0741 (17)	0.0825 (17)	0.0757 (16)	−0.0296 (14)	−0.0218 (13)	−0.0128 (13)
C3	0.071 (2)	0.064 (2)	0.049 (2)	−0.0329 (19)	−0.0129 (17)	−0.0043 (16)
O4	0.0734 (18)	0.0837 (19)	0.115 (2)	−0.0163 (15)	−0.0312 (16)	0.0002 (16)
C4	0.077 (2)	0.090 (3)	0.053 (2)	−0.038 (2)	−0.0138 (18)	−0.0091 (18)
O5	0.119 (2)	0.119 (2)	0.107 (2)	−0.0741 (19)	−0.0543 (18)	0.0085 (17)
C5	0.066 (3)	0.093 (3)	0.052 (2)	−0.029 (2)	−0.0045 (18)	−0.0272 (19)
C6	0.085 (3)	0.061 (2)	0.0486 (19)	−0.031 (2)	−0.0210 (19)	−0.0049 (16)
C7	0.092 (3)	0.069 (2)	0.064 (2)	−0.031 (2)	−0.0183 (19)	−0.0250 (18)
C8	0.109 (3)	0.094 (3)	0.094 (3)	−0.034 (2)	−0.040 (2)	−0.034 (2)
C9	0.073 (3)	0.083 (3)	0.061 (2)	−0.031 (2)	−0.0113 (18)	−0.0150 (18)
C10	0.072 (3)	0.164 (4)	0.107 (3)	−0.034 (3)	−0.013 (2)	−0.044 (3)
C11	0.076 (2)	0.076 (2)	0.056 (2)	−0.0347 (19)	−0.0203 (18)	−0.0037 (18)
C12	0.073 (2)	0.061 (2)	0.057 (2)	−0.0326 (18)	−0.0198 (18)	−0.0003 (16)
C13	0.075 (2)	0.060 (2)	0.056 (2)	−0.033 (2)	−0.0224 (19)	0.0031 (17)
C14	0.071 (2)	0.075 (2)	0.070 (2)	−0.030 (2)	−0.0188 (19)	−0.0130 (19)
C15	0.077 (2)	0.067 (2)	0.054 (2)	−0.0280 (19)	−0.0236 (18)	−0.0077 (16)
C16	0.077 (2)	0.069 (2)	0.064 (2)	−0.034 (2)	−0.0300 (19)	−0.0003 (18)
C17	0.073 (2)	0.068 (2)	0.070 (2)	−0.0294 (19)	−0.0264 (19)	−0.0051 (18)
C18	0.090 (3)	0.062 (2)	0.0441 (18)	−0.0403 (19)	−0.0271 (18)	0.0134 (15)
C19	0.073 (2)	0.055 (2)	0.0463 (19)	−0.0253 (18)	−0.0251 (17)	0.0044 (16)
C20	0.087 (3)	0.059 (2)	0.058 (2)	−0.034 (2)	−0.035 (2)	0.0094 (17)
C21	0.081 (3)	0.076 (3)	0.066 (2)	−0.038 (2)	−0.028 (2)	0.011 (2)
C22	0.071 (3)	0.065 (2)	0.083 (3)	−0.024 (2)	−0.038 (2)	0.000 (2)
C23	0.085 (3)	0.065 (2)	0.092 (3)	−0.027 (2)	−0.045 (2)	0.013 (2)
C24	0.089 (3)	0.064 (2)	0.072 (2)	−0.032 (2)	−0.038 (2)	0.0120 (19)
C25	0.093 (3)	0.093 (3)	0.138 (4)	−0.012 (3)	−0.039 (3)	0.001 (3)
C26	0.071 (2)	0.055 (2)	0.0467 (18)	−0.0272 (17)	−0.0194 (16)	0.0001 (15)
C27	0.094 (3)	0.072 (2)	0.066 (2)	−0.045 (2)	−0.032 (2)	0.0218 (18)
C28	0.091 (3)	0.080 (3)	0.092 (3)	−0.053 (2)	−0.028 (2)	0.013 (2)
C29	0.074 (2)	0.067 (2)	0.073 (2)	−0.034 (2)	−0.029 (2)	0.0026 (19)
C30	0.093 (3)	0.077 (2)	0.061 (2)	−0.045 (2)	−0.036 (2)	0.0139 (18)
C31	0.090 (3)	0.069 (2)	0.060 (2)	−0.050 (2)	−0.0307 (19)	0.0155 (17)
C32	0.115 (4)	0.148 (4)	0.134 (4)	−0.086 (4)	−0.034 (3)	−0.004 (3)
O6	0.199 (4)	0.113 (3)	0.144 (3)	−0.018 (3)	0.029 (3)	−0.019 (2)
C33	0.248 (11)	0.302 (12)	0.253 (12)	−0.032 (9)	−0.051 (9)	0.022 (10)
C34	0.199 (9)	0.263 (10)	0.248 (11)	0.059 (7)	−0.098 (8)	−0.100 (9)
O7	0.131 (3)	0.178 (4)	0.194 (4)	−0.052 (3)	−0.050 (3)	−0.017 (3)
C36	0.260 (12)	0.305 (14)	0.204 (10)	−0.022 (10)	−0.010 (8)	0.022 (10)
C35	0.219 (10)	0.438 (18)	0.440 (19)	−0.089 (11)	−0.006 (12)	−0.233 (16)

Geometric parameters (Å, º) top

O1—C1	1.357 (3)	C16—H16B	0.9700
O1—C9	1.441 (3)	C17—H17A	0.9700
N1—C13	1.358 (4)	C17—H17B	0.9700
N1—C17	1.453 (4)	C18—C19	1.520 (4)
N1—C14	1.461 (4)	C18—C26	1.525 (4)
C1—C2	1.352 (4)	C18—H18A	0.9800
C1—C6	1.420 (4)	C19—C20	1.366 (4)
O2—C6	1.363 (4)	C19—C24	1.380 (4)
O2—C7	1.434 (3)	C20—C21	1.393 (4)
N2—C15	1.452 (3)	C20—H20A	0.9300
N2—C16	1.462 (4)	C21—C22	1.371 (4)
N2—C18	1.470 (4)	C21—H21A	0.9300
C2—C3	1.396 (4)	C22—C23	1.371 (5)
C2—H2A	0.9300	C23—C24	1.373 (4)
O3—C13	1.243 (4)	C23—H23A	0.9300
C3—C4	1.391 (4)	C24—H24A	0.9300
C3—C11	1.455 (4)	C25—H25A	0.9600
O4—C22	1.369 (4)	C25—H25B	0.9600
O4—C25	1.415 (4)	C25—H25C	0.9600
C4—C5	1.370 (4)	C26—C27	1.360 (4)
C4—H4A	0.9300	C26—C31	1.393 (4)
O5—C29	1.392 (4)	C27—C28	1.372 (4)
O5—C32	1.401 (4)	C27—H27A	0.9300
C5—C6	1.360 (4)	C28—C29	1.364 (5)
C5—H5A	0.9300	C28—H28A	0.9300
C7—C8	1.480 (4)	C29—C30	1.362 (4)
C7—H7A	0.9700	C30—C31	1.368 (4)
C7—H7B	0.9700	C30—H30A	0.9300
C8—H8A	0.9600	C31—H31A	0.9300
C8—H8B	0.9600	C32—H32A	0.9600
C8—H8C	0.9600	C32—H32B	0.9600
C9—C10	1.493 (4)	C32—H32C	0.9600
C9—H9A	0.9700	O6—C34	1.533 (10)
C9—H9B	0.9700	O6—H6A	0.8200
C10—H10A	0.9600	C33—C34	1.405 (7)
C10—H10B	0.9600	C33—H33A	0.9600
C10—H10C	0.9600	C33—H33B	0.9600
C11—C12	1.306 (4)	C33—H33C	0.9600
C11—H11A	0.9300	C34—H34C	0.9700
C12—C13	1.456 (4)	C34—H34D	0.9700
C12—H12A	0.9300	O7—C36	1.459 (10)
C14—C15	1.514 (4)	O7—H7C	0.8200
C14—H14A	0.9700	C36—C35	1.409 (8)
C14—H14B	0.9700	C36—H36A	0.9700
C15—H15A	0.9700	C36—H36B	0.9700
C15—H15B	0.9700	C35—H35A	0.9600
C16—C17	1.518 (4)	C35—H35B	0.9600
C16—H16A	0.9700	C35—H35C	0.9600

C1—O1—C9	117.0 (2)	C16—C17—H17B	109.6
C13—N1—C17	121.6 (3)	H17A—C17—H17B	108.1
C13—N1—C14	126.5 (3)	N2—C18—C19	112.0 (3)
C17—N1—C14	111.9 (2)	N2—C18—C26	111.4 (3)
C2—C1—O1	125.7 (3)	C19—C18—C26	110.1 (2)
C2—C1—C6	119.4 (3)	N2—C18—H18A	107.7
O1—C1—C6	114.8 (3)	C19—C18—H18A	107.7
C6—O2—C7	117.1 (3)	C26—C18—H18A	107.7
C15—N2—C16	108.0 (2)	C20—C19—C24	118.5 (3)
C15—N2—C18	112.1 (2)	C20—C19—C18	121.8 (3)
C16—N2—C18	111.6 (2)	C24—C19—C18	119.6 (3)
C1—C2—C3	122.4 (3)	C19—C20—C21	120.3 (3)
C1—C2—H2A	118.8	C19—C20—H20A	119.8
C3—C2—H2A	118.8	C21—C20—H20A	119.8
C4—C3—C2	116.7 (3)	C22—C21—C20	120.5 (3)
C4—C3—C11	119.5 (3)	C22—C21—H21A	119.7
C2—C3—C11	123.8 (3)	C20—C21—H21A	119.7
C22—O4—C25	117.5 (3)	O4—C22—C21	115.6 (4)
C5—C4—C3	121.9 (3)	O4—C22—C23	125.3 (4)
C5—C4—H4A	119.0	C21—C22—C23	119.1 (4)
C3—C4—H4A	119.0	C22—C23—C24	120.2 (4)
C29—O5—C32	117.8 (3)	C22—C23—H23A	119.9
C6—C5—C4	120.6 (3)	C24—C23—H23A	119.9
C6—C5—H5A	119.7	C23—C24—C19	121.3 (4)
C4—C5—H5A	119.7	C23—C24—H24A	119.4
C5—C6—O2	124.9 (3)	C19—C24—H24A	119.4
C5—C6—C1	118.9 (3)	O4—C25—H25A	109.5
O2—C6—C1	116.2 (3)	O4—C25—H25B	109.5
O2—C7—C8	108.3 (3)	H25A—C25—H25B	109.5
O2—C7—H7A	110.0	O4—C25—H25C	109.5
C8—C7—H7A	110.0	H25A—C25—H25C	109.5
O2—C7—H7B	110.0	H25B—C25—H25C	109.5
C8—C7—H7B	110.0	C27—C26—C31	118.5 (3)
H7A—C7—H7B	108.4	C27—C26—C18	120.8 (3)
C7—C8—H8A	109.5	C31—C26—C18	120.6 (3)
C7—C8—H8B	109.5	C26—C27—C28	120.9 (3)
H8A—C8—H8B	109.5	C26—C27—H27A	119.6
C7—C8—H8C	109.5	C28—C27—H27A	119.6
H8A—C8—H8C	109.5	C29—C28—C27	120.3 (3)
H8B—C8—H8C	109.5	C29—C28—H28A	119.9
O1—C9—C10	107.5 (3)	C27—C28—H28A	119.9
O1—C9—H9A	110.2	C30—C29—C28	119.7 (3)
C10—C9—H9A	110.2	C30—C29—O5	115.6 (3)
O1—C9—H9B	110.2	C28—C29—O5	124.7 (3)
C10—C9—H9B	110.2	C29—C30—C31	120.3 (3)
H9A—C9—H9B	108.5	C29—C30—H30A	119.8
C9—C10—H10A	109.5	C31—C30—H30A	119.8
C9—C10—H10B	109.5	C30—C31—C26	120.3 (3)
H10A—C10—H10B	109.5	C30—C31—H31A	119.9
C9—C10—H10C	109.5	C26—C31—H31A	119.9
H10A—C10—H10C	109.5	O5—C32—H32A	109.5
H10B—C10—H10C	109.5	O5—C32—H32B	109.5
C12—C11—C3	129.4 (3)	H32A—C32—H32B	109.5
C12—C11—H11A	115.3	O5—C32—H32C	109.5
C3—C11—H11A	115.3	H32A—C32—H32C	109.5
C11—C12—C13	120.8 (3)	H32B—C32—H32C	109.5
C11—C12—H12A	119.6	C34—O6—H6A	109.5
C13—C12—H12A	119.6	C34—C33—H33A	109.5
O3—C13—N1	118.7 (3)	C34—C33—H33B	109.5
O3—C13—C12	121.2 (3)	H33A—C33—H33B	109.5
N1—C13—C12	120.0 (3)	C34—C33—H33C	109.5
N1—C14—C15	110.5 (3)	H33A—C33—H33C	109.5
N1—C14—H14A	109.5	H33B—C33—H33C	109.5
C15—C14—H14A	109.5	C33—C34—O6	92.2 (8)
N1—C14—H14B	109.5	C33—C34—H34C	113.3
C15—C14—H14B	109.5	O6—C34—H34C	113.3
H14A—C14—H14B	108.1	C33—C34—H34D	113.3
N2—C15—C14	111.0 (3)	O6—C34—H34D	113.3
N2—C15—H15A	109.4	H34C—C34—H34D	110.6
C14—C15—H15A	109.4	C36—O7—H7C	109.5
N2—C15—H15B	109.4	C35—C36—O7	102.2 (9)
C14—C15—H15B	109.4	C35—C36—H36A	111.3
H15A—C15—H15B	108.0	O7—C36—H36A	111.3
N2—C16—C17	111.2 (3)	C35—C36—H36B	111.3
N2—C16—H16A	109.4	O7—C36—H36B	111.3
C17—C16—H16A	109.4	H36A—C36—H36B	109.2
N2—C16—H16B	109.4	C36—C35—H35A	109.5
C17—C16—H16B	109.4	C36—C35—H35B	109.5
H16A—C16—H16B	108.0	H35A—C35—H35B	109.5
N1—C17—C16	110.3 (3)	C36—C35—H35C	109.5
N1—C17—H17A	109.6	H35A—C35—H35C	109.5
C16—C17—H17A	109.6	H35B—C35—H35C	109.5
N1—C17—H17B	109.6

C9—O1—C1—C2	9.1 (5)	N2—C16—C17—N1	−57.4 (3)
C9—O1—C1—C6	−169.3 (3)	C15—N2—C18—C19	−55.2 (3)
O1—C1—C2—C3	−179.8 (3)	C16—N2—C18—C19	−176.5 (2)
C6—C1—C2—C3	−1.5 (5)	C15—N2—C18—C26	−179.0 (3)
C1—C2—C3—C4	0.4 (5)	C16—N2—C18—C26	59.7 (3)
C1—C2—C3—C11	178.0 (3)	N2—C18—C19—C20	−44.4 (4)
C2—C3—C4—C5	−0.2 (5)	C26—C18—C19—C20	80.2 (4)
C11—C3—C4—C5	−177.9 (3)	N2—C18—C19—C24	140.3 (3)
C3—C4—C5—C6	1.1 (6)	C26—C18—C19—C24	−95.1 (3)
C4—C5—C6—O2	178.0 (3)	C24—C19—C20—C21	0.0 (4)
C4—C5—C6—C1	−2.2 (5)	C18—C19—C20—C21	−175.3 (3)
C7—O2—C6—C5	−7.3 (5)	C19—C20—C21—C22	0.8 (5)
C7—O2—C6—C1	172.9 (3)	C25—O4—C22—C21	−179.2 (3)
C2—C1—C6—C5	2.4 (5)	C25—O4—C22—C23	2.0 (5)
O1—C1—C6—C5	−179.2 (3)	C20—C21—C22—O4	179.7 (3)
C2—C1—C6—O2	−177.8 (3)	C20—C21—C22—C23	−1.4 (5)
O1—C1—C6—O2	0.6 (4)	O4—C22—C23—C24	−179.9 (3)
C6—O2—C7—C8	−174.7 (3)	C21—C22—C23—C24	1.3 (5)
C1—O1—C9—C10	174.0 (3)	C22—C23—C24—C19	−0.6 (5)
C4—C3—C11—C12	171.2 (3)	C20—C19—C24—C23	−0.1 (5)
C2—C3—C11—C12	−6.3 (6)	C18—C19—C24—C23	175.3 (3)
C3—C11—C12—C13	−180.0 (3)	N2—C18—C26—C27	−137.3 (3)
C17—N1—C13—O3	−0.3 (5)	C19—C18—C26—C27	97.8 (4)
C14—N1—C13—O3	−178.8 (3)	N2—C18—C26—C31	46.5 (4)
C17—N1—C13—C12	178.3 (3)	C19—C18—C26—C31	−78.3 (4)
C14—N1—C13—C12	−0.2 (5)	C31—C26—C27—C28	0.2 (5)
C11—C12—C13—O3	7.8 (5)	C18—C26—C27—C28	−176.1 (3)
C11—C12—C13—N1	−170.8 (3)	C26—C27—C28—C29	−0.7 (5)
C13—N1—C14—C15	124.4 (3)	C27—C28—C29—C30	0.6 (5)
C17—N1—C14—C15	−54.2 (4)	C27—C28—C29—O5	178.8 (3)
C16—N2—C15—C14	−60.2 (3)	C32—O5—C29—C30	−173.3 (3)
C18—N2—C15—C14	176.4 (3)	C32—O5—C29—C28	8.4 (5)
N1—C14—C15—N2	57.9 (3)	C28—C29—C30—C31	0.1 (5)
C15—N2—C16—C17	60.1 (3)	O5—C29—C30—C31	−178.3 (3)
C18—N2—C16—C17	−176.2 (2)	C29—C30—C31—C26	−0.6 (5)
C13—N1—C17—C16	−124.8 (3)	C27—C26—C31—C30	0.5 (5)
C14—N1—C17—C16	53.9 (4)	C18—C26—C31—C30	176.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O3	0.82	1.97	2.699 (4)	147
O7—H7C···O6	0.82	1.91	2.730 (6)	178
C14—H14A···O7ⁱ	0.97	2.54	3.436 (7)	153
C32—H32A···O4ⁱⁱ	0.96	2.57	3.258 (6)	129

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

Experimental details

Crystal data
Chemical formula	C₃₂H₃₈N₂O₅·2C₂H₆O
M_r	622.78
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	12.511 (3), 12.564 (3), 13.601 (3)
α, β, γ (°)	88.13 (3), 70.62 (3), 65.84 (3)
V (Å³)	1826.9 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.977, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	6687, 6687, 2904
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.166, 1.00
No. of reflections	6687
No. of parameters	412
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.16

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
O6—H6A···O3	0.82	1.97	2.699 (4)	146.9
O7—H7C···O6	0.82	1.91	2.730 (6)	177.5
C14—H14A···O7ⁱ	0.97	2.54	3.436 (7)	153
C32—H32A···O4ⁱⁱ	0.96	2.57	3.258 (6)	129

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

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 the Education Department of Jiangsu Province (grant No. 05KJB350084) and 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. & Wu, B. (2011). Acta Cryst. E67, o2791. Web of Science CSD CrossRef IUCr Journals Google Scholar

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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