1-Benzyl-3,5-bis­(4-methyl­benzyl­idene)-4-oxopiperidin-1-ium chloride acetic acid monosolvate

Sun, J.; Xing, J.; Han, J.

doi:10.1107/S1600536811016138

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1350

doi:10.1107/S1600536811016138

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1-Benzyl-3,5-bis(4-methylbenzylidene)-4-oxopiperidin-1-ium chloride acetic acid monosolvate

Ju-feng Sun,^a ^* Juan Xing ^a and Jing-tian Han ^a

^aBinzhou Medical College, Yantai 264003, People's Republic of China
^*Correspondence e-mail: sjf.xzy@163.com

(Received 22 April 2011; accepted 28 April 2011; online 7 May 2011)

In the title solvated molecular salt, C₂₈H₂₈NO⁺·Cl⁻·C₂H₄O₂, the central piperidinium ring of the cation adopts an envelope conformation with the N atom displaced by 0.798 (2) Å from the mean plane of the five C atoms. In the crystal, the components are linked by N—H⋯Cl and O—H⋯Cl hydrogen bonds into trimeric assemblies. C—H⋯Cl and C—H⋯π interactions further consolidate the packing.

Related literature

For background to the use of piperidone derivatives in medicine, see: Dimmock et al. (2003 ); El-Subbagh et al. (2000 ); Pati et al. (2009 ); Das et al. (2009 , 2010 ). For the synthesis, see: Pati et al. (2009).

Experimental

Crystal data

C₂₈H₂₈NO⁺·Cl⁻·C₂H₄O₂
M_r = 490.02
Triclinic, $[P \overline 1]$
a = 7.1488 (5) Å
b = 11.2799 (7) Å
c = 17.6271 (11) Å
α = 103.181 (6)°
β = 98.087 (6)°
γ = 92.407 (6)°
V = 1366.16 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 288 K
0.61 × 0.54 × 0.52 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction, Yarnton, England.]$ ) T_min = 0.804, T_max = 1.000
16829 measured reflections
5549 independent reflections
3895 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.158
S = 1.03
5549 reflections
320 parameters
39 restraints
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1	0.91	2.15	3.0490 (17)	171
O3—H3⋯Cl1	0.82	2.26	3.053 (2)	162
C11—H11A⋯Cl1ⁱ	0.97	2.72	3.602 (2)	151
C25—H25⋯Cg3ⁱⁱ	0.93	2.85	3.582 (4)	137
C30—H30C⋯Cg3ⁱⁱⁱ	0.97	2.96	3.675 (4)	133
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y-1, -z; (iii) x, y-1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016138/hb5860sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016138/hb5860Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811016138/hb5860Isup3.cml

checkCIF report

Comment top

At present, a series of N-substituted-3,5-bis(arylidene)-4-piperidone derivatives have been synthesized and proved to be a kind of lead tumor-specific cytotoxin which induces apoptosis and autophagy with multidrug-resistance reverting properties (Pati et al. 2009; Das et al. 2009; Das et al. 2010). These compounds have a marked affinity for thiols in contrast to amino and hydroxyl groups found in nucleic acids (Dimmock et al. 2003). Thus development of these compounds as candidate cytotoxics may lead to drugs which are lack of the genotoxic properties present in various antineoplastic agents (El-Subbagh et al. 2000). Here, we report the title compound (I), whose IC₅₀ (µM) to HL-60 and HSC-2 cells are 59.80 and 105.09 could be used as a basic unit to prepare antineoplastic compounds.

The molecular structure of the title compound (I) is shown in Fig. 1. The hydrogen proton of hydrogen chloride have completely transferred to N1, resulting in the formation of ammonium salt, in which the hydrogen-bonding donors and acceptors reside separately on the cations and anions. In the crystal, weak intermolecular N—H···Cl hydrogen bonds, C—H···Cl hydrogen bonds, O—H···Cl hydrogen bonds and C—H···π stacking interactions contribute to the crystal packing arrangement (Table 1).

Related literature top

For background to the use of piperidone derivatives in medicine, see: Dimmock et al. (2003); El-Subbagh et al. (2000); Pati et al. (2009); Das et al. (2009, 2010). For the synthesis, see: Pati et al. (2009).

Experimental top

The title compound was synthesized according to the literature (Pati et al. 2009). Dry hydrogen chloride was continuously bubbled into a solution of N-benzyl-4-piperidone (0.005 mol) and p-tolualdehyde (0.01 mol) in acetic acid (15 ml) at room temperature. And then the mixture was stirred at room temperature for 12 h. When the produced precipitate was collected, they were added to a solution of aqueous potassium carbonate solution (25%, w/v). The desired product was obtained after the solid was crystallized by the mixed solvents of ethanol and chloroform (5:1, v/v) in a yield of 74.8%. Yellow blocks of (I) were obtained by slow evaporation of the reacting solution of the title compound in acetic acid.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids.

1-Benzyl-3,5-bis(4-methylbenzylidene)-4-oxopiperidin-1-ium chloride acetic acid monosolvate top

Crystal data top

C₂₈H₂₈NO⁺·Cl⁻·C₂H₄O₂	Z = 2
M_r = 490.02	F(000) = 520
Triclinic, P1	D_x = 1.191 Mg m⁻³
a = 7.1488 (5) Å	Mo Kα radiation, λ = 0.7107 Å
b = 11.2799 (7) Å	Cell parameters from 6467 reflections
c = 17.6271 (11) Å	θ = 3.3–28.9°
α = 103.181 (6)°	µ = 0.17 mm⁻¹
β = 98.087 (6)°	T = 288 K
γ = 92.407 (6)°	Block, yellow
V = 1366.16 (16) Å³	0.61 × 0.54 × 0.52 mm

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	5549 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3895 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 16.0355 pixels mm^-1	θ_max = 26.4°, θ_min = 3.3°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −14→14
T_min = 0.804, T_max = 1.000	l = −22→22
16829 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0749P)² + 0.3122P] where P = (F_o² + 2F_c²)/3
5549 reflections	(Δ/σ)_max < 0.001
320 parameters	Δρ_max = 0.30 e Å⁻³
39 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₈H₂₈NO⁺·Cl⁻·C₂H₄O₂	γ = 92.407 (6)°
M_r = 490.02	V = 1366.16 (16) Å³
Triclinic, P1	Z = 2
a = 7.1488 (5) Å	Mo Kα radiation
b = 11.2799 (7) Å	µ = 0.17 mm⁻¹
c = 17.6271 (11) Å	T = 288 K
α = 103.181 (6)°	0.61 × 0.54 × 0.52 mm
β = 98.087 (6)°

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	5549 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	3895 reflections with I > 2σ(I)
T_min = 0.804, T_max = 1.000	R_int = 0.029
16829 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	39 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.03	Δρ_max = 0.30 e Å⁻³
5549 reflections	Δρ_min = −0.29 e Å⁻³
320 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
Cl1	0.08804 (8)	0.75303 (7)	0.28289 (4)	0.0748 (3)
N1	0.5035 (2)	0.71709 (14)	0.26944 (10)	0.0393 (4)
H1	0.3839	0.7342	0.2781	0.047*
C9	0.3879 (3)	0.65470 (19)	0.12495 (12)	0.0419 (5)
O1	0.2783 (2)	0.82076 (15)	0.07466 (10)	0.0620 (5)
C13	0.3747 (3)	0.7863 (2)	0.12748 (13)	0.0449 (5)
C12	0.4888 (3)	0.87647 (18)	0.19513 (12)	0.0416 (5)
C11	0.6027 (3)	0.82996 (18)	0.25930 (12)	0.0426 (5)
H11A	0.7271	0.8123	0.2457	0.051*
H11B	0.6192	0.8920	0.3084	0.051*
C10	0.4892 (3)	0.61825 (18)	0.19628 (12)	0.0437 (5)
H10A	0.4218	0.5462	0.2035	0.052*
H10B	0.6156	0.5973	0.1871	0.052*
C5	0.3050 (3)	0.4412 (2)	0.03506 (12)	0.0469 (5)
C8	0.3123 (3)	0.5739 (2)	0.05816 (13)	0.0468 (5)
H8	0.2536	0.6094	0.0193	0.056*
C14	0.4858 (3)	0.9947 (2)	0.19560 (13)	0.0498 (5)
H14	0.3996	1.0132	0.1561	0.060*
C4	0.1820 (3)	0.3827 (2)	−0.03376 (13)	0.0538 (6)
H4	0.1132	0.4299	−0.0629	0.065*
C22	0.5994 (3)	0.6717 (2)	0.33817 (12)	0.0502 (5)
H22A	0.5301	0.5970	0.3402	0.060*
H22B	0.7261	0.6518	0.3288	0.060*
C23	0.6138 (3)	0.7602 (2)	0.41694 (13)	0.0522 (6)
C6	0.4122 (3)	0.3656 (2)	0.07377 (14)	0.0543 (6)
H6	0.5010	0.4004	0.1180	0.065*
C15	0.5982 (4)	1.0990 (2)	0.24915 (13)	0.0557 (6)
C2	0.2600 (3)	0.1835 (2)	−0.01829 (14)	0.0571 (6)
C28	0.7816 (4)	0.8286 (3)	0.45080 (15)	0.0677 (7)
H28	0.8854	0.8218	0.4240	0.081*
C3	0.1601 (3)	0.2573 (2)	−0.05945 (14)	0.0591 (6)
H3A	0.0767	0.2218	−0.1052	0.071*
C7	0.3887 (4)	0.2404 (2)	0.04754 (14)	0.0583 (6)
H7	0.4615	0.1927	0.0749	0.070*
C24	0.4610 (4)	0.7721 (3)	0.45812 (16)	0.0724 (8)
H24	0.3459	0.7279	0.4360	0.087*
C20	0.7861 (4)	1.0932 (2)	0.28108 (15)	0.0649 (7)
H20	0.8430	1.0198	0.2699	0.078*
C19	0.8889 (5)	1.1962 (3)	0.32947 (17)	0.0867 (9)
H19	1.0147	1.1917	0.3502	0.104*
C1	0.2305 (5)	0.0466 (2)	−0.04400 (18)	0.0793 (8)
H1A	0.1202	0.0239	−0.0836	0.119*
H1B	0.2132	0.0140	0.0005	0.119*
H1C	0.3394	0.0145	−0.0653	0.119*
C16	0.5197 (5)	1.2108 (2)	0.26610 (17)	0.0773 (8)
H16	0.3962	1.2174	0.2434	0.093*
C27	0.7962 (5)	0.9078 (3)	0.52492 (17)	0.0869 (10)
H27	0.9094	0.9542	0.5472	0.104*
C18	0.8059 (6)	1.3060 (3)	0.34730 (18)	0.0944 (10)
C25	0.4813 (6)	0.8509 (4)	0.53299 (19)	0.0936 (11)
H25	0.3800	0.8573	0.5611	0.112*
C26	0.6465 (7)	0.9179 (3)	0.56492 (18)	0.0940 (11)
H26	0.6576	0.9710	0.6144	0.113*
C17	0.6200 (6)	1.3104 (3)	0.3151 (2)	0.0997 (11)
H17	0.5620	1.3831	0.3273	0.120*
O2	0.1938 (3)	0.4138 (2)	0.24132 (14)	0.0879 (6)
O3	−0.0627 (3)	0.4934 (2)	0.19550 (14)	0.0900 (7)
H3	−0.0103	0.5553	0.2265	0.135*
C29	0.0411 (4)	0.4005 (3)	0.19967 (18)	0.0713 (8)
C30	−0.0443 (5)	0.2837 (3)	0.1471 (2)	0.0894 (9)
H30A	−0.0568	0.2901	0.0932	0.134*
H30B	−0.1671	0.2656	0.1596	0.134*
H30C	0.0355	0.2195	0.1541	0.134*
C21	0.9236 (8)	1.4166 (4)	0.4024 (3)	0.1380 (15)
H21A	1.0508	1.3954	0.4156	0.207*
H21B	0.8685	1.4410	0.4496	0.207*
H21C	0.9255	1.4828	0.3765	0.207*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0409 (4)	0.1028 (6)	0.0838 (5)	0.0246 (3)	0.0192 (3)	0.0190 (4)
N1	0.0316 (8)	0.0463 (9)	0.0458 (9)	0.0111 (7)	0.0108 (7)	0.0182 (7)
C9	0.0290 (10)	0.0530 (12)	0.0471 (12)	0.0065 (8)	0.0079 (8)	0.0170 (9)
O1	0.0554 (10)	0.0650 (10)	0.0671 (11)	0.0056 (8)	−0.0080 (8)	0.0292 (8)
C13	0.0328 (10)	0.0563 (12)	0.0514 (12)	0.0071 (9)	0.0078 (9)	0.0233 (10)
C12	0.0329 (10)	0.0491 (11)	0.0488 (12)	0.0089 (8)	0.0123 (8)	0.0193 (9)
C11	0.0359 (11)	0.0452 (11)	0.0491 (12)	0.0067 (8)	0.0065 (9)	0.0155 (9)
C10	0.0402 (11)	0.0442 (11)	0.0488 (12)	0.0089 (9)	0.0074 (9)	0.0138 (9)
C5	0.0365 (11)	0.0590 (13)	0.0461 (12)	0.0046 (9)	0.0107 (9)	0.0114 (10)
C8	0.0339 (11)	0.0616 (13)	0.0488 (12)	0.0076 (9)	0.0064 (9)	0.0207 (10)
C14	0.0503 (13)	0.0547 (13)	0.0508 (12)	0.0127 (10)	0.0088 (10)	0.0232 (10)
C4	0.0383 (12)	0.0723 (16)	0.0496 (13)	0.0066 (11)	0.0051 (9)	0.0123 (11)
C22	0.0541 (13)	0.0519 (12)	0.0509 (13)	0.0162 (10)	0.0073 (10)	0.0235 (10)
C23	0.0595 (14)	0.0587 (13)	0.0469 (12)	0.0178 (11)	0.0111 (10)	0.0258 (10)
C6	0.0517 (14)	0.0603 (14)	0.0477 (12)	0.0081 (11)	0.0014 (10)	0.0093 (10)
C15	0.0758 (16)	0.0502 (12)	0.0460 (12)	0.0097 (11)	0.0086 (11)	0.0211 (10)
C2	0.0551 (14)	0.0621 (14)	0.0543 (14)	−0.0026 (11)	0.0239 (11)	0.0060 (11)
C28	0.0702 (18)	0.0816 (18)	0.0539 (15)	0.0056 (14)	0.0070 (13)	0.0229 (13)
C3	0.0421 (13)	0.0734 (16)	0.0532 (13)	−0.0062 (11)	0.0077 (10)	−0.0008 (12)
C7	0.0685 (16)	0.0557 (14)	0.0511 (13)	0.0095 (12)	0.0099 (11)	0.0123 (11)
C24	0.0694 (18)	0.098 (2)	0.0609 (16)	0.0197 (15)	0.0209 (13)	0.0324 (15)
C20	0.0783 (17)	0.0536 (13)	0.0644 (15)	−0.0023 (12)	0.0025 (13)	0.0235 (11)
C19	0.107 (2)	0.0785 (17)	0.0695 (17)	−0.0101 (15)	−0.0170 (15)	0.0289 (14)
C1	0.095 (2)	0.0636 (17)	0.0759 (18)	−0.0121 (15)	0.0294 (16)	0.0030 (14)
C16	0.114 (2)	0.0523 (14)	0.0656 (16)	0.0224 (14)	0.0013 (15)	0.0184 (12)
C27	0.113 (3)	0.086 (2)	0.0567 (17)	−0.0024 (19)	−0.0056 (17)	0.0195 (15)
C18	0.150 (3)	0.0600 (15)	0.0632 (17)	−0.0108 (17)	−0.0071 (18)	0.0127 (13)
C25	0.112 (3)	0.125 (3)	0.0609 (18)	0.046 (2)	0.0394 (18)	0.0355 (19)
C26	0.144 (4)	0.092 (2)	0.0497 (17)	0.034 (2)	0.017 (2)	0.0177 (15)
C17	0.149 (3)	0.0584 (16)	0.085 (2)	0.0182 (17)	−0.004 (2)	0.0138 (14)
O2	0.0612 (13)	0.1007 (15)	0.1090 (16)	0.0147 (11)	0.0039 (12)	0.0436 (13)
O3	0.0621 (13)	0.1004 (16)	0.1116 (18)	0.0188 (12)	−0.0014 (11)	0.0401 (14)
C29	0.0529 (16)	0.095 (2)	0.0828 (19)	0.0131 (15)	0.0192 (14)	0.0479 (17)
C30	0.085 (2)	0.092 (2)	0.096 (2)	−0.0020 (18)	0.0156 (18)	0.0338 (19)
C21	0.181 (3)	0.100 (2)	0.105 (2)	−0.017 (2)	−0.024 (2)	0.001 (2)

Geometric parameters (Å, º) top

N1—H1	0.9100	C2—C1	1.504 (4)
N1—C11	1.490 (3)	C28—H28	0.9300
N1—C10	1.488 (3)	C28—C27	1.392 (4)
N1—C22	1.510 (3)	C3—H3A	0.9300
C9—C13	1.482 (3)	C7—H7	0.9300
C9—C10	1.510 (3)	C24—H24	0.9300
C9—C8	1.341 (3)	C24—C25	1.398 (4)
O1—C13	1.225 (2)	C20—H20	0.9300
C13—C12	1.492 (3)	C20—C19	1.385 (4)
C12—C11	1.505 (3)	C19—H19	0.9300
C12—C14	1.333 (3)	C19—C18	1.386 (5)
C11—H11A	0.9700	C1—H1A	0.9600
C11—H11B	0.9700	C1—H1B	0.9600
C10—H10A	0.9700	C1—H1C	0.9600
C10—H10B	0.9700	C16—H16	0.9300
C5—C8	1.456 (3)	C16—C17	1.356 (4)
C5—C4	1.402 (3)	C27—H27	0.9300
C5—C6	1.397 (3)	C27—C26	1.357 (5)
C8—H8	0.9300	C18—C17	1.377 (5)
C14—H14	0.9300	C18—C21	1.528 (5)
C14—C15	1.457 (3)	C25—H25	0.9300
C4—H4	0.9300	C25—C26	1.352 (5)
C4—C3	1.378 (3)	C26—H26	0.9300
C22—H22A	0.9700	C17—H17	0.9300
C22—H22B	0.9700	O2—C29	1.210 (3)
C22—C23	1.501 (3)	O3—H3	0.8200
C23—C28	1.379 (4)	O3—C29	1.320 (3)
C23—C24	1.388 (3)	C29—C30	1.478 (4)
C6—H6	0.9300	C30—H30A	0.9600
C6—C7	1.377 (3)	C30—H30B	0.9600
C15—C20	1.392 (4)	C30—H30C	0.9600
C15—C16	1.389 (3)	C21—H21A	0.9600
C2—C3	1.382 (4)	C21—H21B	0.9600
C2—C7	1.384 (3)	C21—H21C	0.9600

C11—N1—H1	108.1	C23—C28—C27	120.2 (3)
C11—N1—C22	113.02 (16)	C27—C28—H28	119.9
C10—N1—H1	108.1	C4—C3—C2	121.1 (2)
C10—N1—C11	110.26 (16)	C4—C3—H3A	119.4
C10—N1—C22	109.03 (14)	C2—C3—H3A	119.4
C22—N1—H1	108.1	C6—C7—C2	122.0 (2)
C13—C9—C10	118.82 (17)	C6—C7—H7	119.0
C8—C9—C13	117.84 (18)	C2—C7—H7	119.0
C8—C9—C10	123.32 (19)	C23—C24—H24	120.2
C9—C13—C12	117.95 (17)	C23—C24—C25	119.6 (3)
O1—C13—C9	121.50 (19)	C25—C24—H24	120.2
O1—C13—C12	120.50 (19)	C15—C20—H20	119.9
C13—C12—C11	118.64 (17)	C19—C20—C15	120.3 (3)
C14—C12—C13	118.29 (19)	C19—C20—H20	119.9
C14—C12—C11	123.07 (19)	C20—C19—H19	119.7
N1—C11—C12	109.89 (16)	C20—C19—C18	120.6 (3)
N1—C11—H11A	109.7	C18—C19—H19	119.7
N1—C11—H11B	109.7	C2—C1—H1A	109.5
C12—C11—H11A	109.7	C2—C1—H1B	109.5
C12—C11—H11B	109.7	C2—C1—H1C	109.5
H11A—C11—H11B	108.2	H1A—C1—H1B	109.5
N1—C10—C9	112.41 (15)	H1A—C1—H1C	109.5
N1—C10—H10A	109.1	H1B—C1—H1C	109.5
N1—C10—H10B	109.1	C15—C16—H16	119.4
C9—C10—H10A	109.1	C17—C16—C15	121.1 (3)
C9—C10—H10B	109.1	C17—C16—H16	119.4
H10A—C10—H10B	107.9	C28—C27—H27	119.7
C4—C5—C8	117.3 (2)	C26—C27—C28	120.5 (3)
C6—C5—C8	126.42 (19)	C26—C27—H27	119.7
C6—C5—C4	116.3 (2)	C19—C18—C21	118.7 (4)
C9—C8—C5	132.1 (2)	C17—C18—C19	118.4 (3)
C9—C8—H8	113.9	C17—C18—C21	122.8 (3)
C5—C8—H8	113.9	C24—C25—H25	119.7
C12—C14—H14	115.4	C26—C25—C24	120.7 (3)
C12—C14—C15	129.2 (2)	C26—C25—H25	119.7
C15—C14—H14	115.4	C27—C26—H26	119.9
C5—C4—H4	119.0	C25—C26—C27	120.2 (3)
C3—C4—C5	121.9 (2)	C25—C26—H26	119.9
C3—C4—H4	119.0	C16—C17—C18	121.4 (3)
N1—C22—H22A	108.6	C16—C17—H17	119.3
N1—C22—H22B	108.6	C18—C17—H17	119.3
H22A—C22—H22B	107.5	C29—O3—H3	109.5
C23—C22—N1	114.79 (16)	O2—C29—O3	121.5 (3)
C23—C22—H22A	108.6	O2—C29—C30	124.9 (3)
C23—C22—H22B	108.6	O3—C29—C30	113.5 (3)
C28—C23—C22	120.3 (2)	C29—C30—H30A	109.5
C28—C23—C24	118.8 (2)	C29—C30—H30B	109.5
C24—C23—C22	120.9 (2)	C29—C30—H30C	109.5
C5—C6—H6	119.4	H30A—C30—H30B	109.5
C7—C6—C5	121.1 (2)	H30A—C30—H30C	109.5
C7—C6—H6	119.4	H30B—C30—H30C	109.5
C20—C15—C14	122.6 (2)	C18—C21—H21A	109.5
C16—C15—C14	119.2 (2)	C18—C21—H21B	109.5
C16—C15—C20	118.1 (2)	C18—C21—H21C	109.5
C3—C2—C7	117.4 (2)	H21A—C21—H21B	109.5
C3—C2—C1	121.4 (2)	H21A—C21—H21C	109.5
C7—C2—C1	121.2 (2)	H21B—C21—H21C	109.5
C23—C28—H28	119.9

N1—C22—C23—C28	−100.9 (2)	C14—C15—C20—C19	177.7 (2)
N1—C22—C23—C24	81.1 (3)	C14—C15—C16—C17	−179.5 (3)
C9—C13—C12—C11	−3.3 (3)	C4—C5—C8—C9	167.5 (2)
C9—C13—C12—C14	176.39 (18)	C4—C5—C6—C7	−3.6 (3)
O1—C13—C12—C11	179.07 (19)	C22—N1—C11—C12	−174.39 (16)
O1—C13—C12—C14	−1.3 (3)	C22—N1—C10—C9	177.83 (17)
C13—C9—C10—N1	20.4 (3)	C22—C23—C28—C27	−178.0 (2)
C13—C9—C8—C5	178.0 (2)	C22—C23—C24—C25	177.0 (2)
C13—C12—C11—N1	−32.5 (2)	C23—C28—C27—C26	0.6 (4)
C13—C12—C14—C15	−172.7 (2)	C23—C24—C25—C26	1.6 (5)
C12—C14—C15—C20	35.2 (4)	C6—C5—C8—C9	−14.1 (4)
C12—C14—C15—C16	−148.4 (3)	C6—C5—C4—C3	3.5 (3)
C11—N1—C10—C9	−57.5 (2)	C15—C20—C19—C18	0.5 (5)
C11—N1—C22—C23	60.2 (2)	C15—C16—C17—C18	2.9 (5)
C11—C12—C14—C15	7.0 (4)	C28—C23—C24—C25	−1.1 (4)
C10—N1—C11—C12	63.3 (2)	C28—C27—C26—C25	0.0 (5)
C10—N1—C22—C23	−176.78 (19)	C3—C2—C7—C6	2.7 (4)
C10—C9—C13—O1	−172.6 (2)	C7—C2—C3—C4	−2.8 (3)
C10—C9—C13—C12	9.8 (3)	C24—C23—C28—C27	0.0 (4)
C10—C9—C8—C5	−0.4 (4)	C24—C25—C26—C27	−1.1 (5)
C5—C4—C3—C2	−0.3 (4)	C20—C15—C16—C17	−2.9 (4)
C5—C6—C7—C2	0.6 (4)	C20—C19—C18—C17	−0.6 (5)
C8—C9—C13—O1	9.0 (3)	C20—C19—C18—C21	178.7 (3)
C8—C9—C13—C12	−168.70 (18)	C19—C18—C17—C16	−1.0 (5)
C8—C9—C10—N1	−161.29 (19)	C1—C2—C3—C4	177.3 (2)
C8—C5—C4—C3	−178.0 (2)	C1—C2—C7—C6	−177.4 (2)
C8—C5—C6—C7	178.0 (2)	C16—C15—C20—C19	1.2 (4)
C14—C12—C11—N1	147.8 (2)	C21—C18—C17—C16	179.6 (4)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.91	2.15	3.0490 (17)	171
O3—H3···Cl1	0.82	2.26	3.053 (2)	162
C11—H11A···Cl1ⁱ	0.97	2.72	3.602 (2)	151
C25—H25···Cg3ⁱⁱ	0.93	2.85	3.582 (4)	137
C30—H30C···Cg3ⁱⁱⁱ	0.97	2.96	3.675 (4)	133

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

Experimental details

Crystal data
Chemical formula	C₂₈H₂₈NO⁺·Cl⁻·C₂H₄O₂
M_r	490.02
Crystal system, space group	Triclinic, P1
Temperature (K)	288
a, b, c (Å)	7.1488 (5), 11.2799 (7), 17.6271 (11)
α, β, γ (°)	103.181 (6), 98.087 (6), 92.407 (6)
V (Å³)	1366.16 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.61 × 0.54 × 0.52

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.804, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	16829, 5549, 3895
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.158, 1.03
No. of reflections	5549
No. of parameters	320
No. of restraints	39
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.29

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.91	2.15	3.0490 (17)	171
O3—H3···Cl1	0.82	2.26	3.053 (2)	162
C11—H11A···Cl1ⁱ	0.97	2.72	3.602 (2)	151
C25—H25···Cg3ⁱⁱ	0.93	2.85	3.582 (4)	137
C30—H30C···Cg3ⁱⁱⁱ	0.97	2.96	3.675 (4)	133

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

Acknowledgements

The authors are grateful to Binzhou Medical College for financial support.

References

Das, S., Das, U., Selvakumar, P., Sharma, R. K., Balzarini, J., Clercq, E. D., Molnar, J., Serly, J., Barath, Z., Schatte, G., Bandy, B., Gorecki, D. K. J. & Dimmock, J. R. (2009). Chem. Med. Chem. 4, 1831–1840. Web of Science CrossRef PubMed CAS Google Scholar
Das, U., Sakagami, H., Chu, Q., Wang, Q., Kawase, M., Selvakuma, P., Sharma, R. K. & Dimmock, J. R. (2010). Bioorg. Med. Chem. Lett. 20, 912–917. Web of Science CrossRef CAS PubMed Google Scholar
Dimmock, J. R., Jha, A., Zello, G. A., Sharma, R. K., Shrivastav, A., Selvakumar, P., Allen, T. M., Santos, C. L., Balzarini, J., Clercq, E. D., Manavathu, E. K. & Stables, J. P. (2003). J. Enzyme Inhib. Med. Chem. 18, 325–332. Web of Science CrossRef PubMed CAS Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
El-Subbagh, H. I., Abu-Zaid, S. M., Mahran, M. A., Badria, F. A. & Al-Obaid, A. M. (2000). J. Med. Chem. 43, 2915–2921. Web of Science CrossRef PubMed CAS Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction, Yarnton, England. Google Scholar
Pati, H. N., Das, U., Das, S. & Bandy, B. (2009). Eur. J. Med. Chem. 44, 54–62. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 6| June 2011| Page o1350

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

1-Benzyl-3,5-bis­­(4-methyl­benzyl­­idene)-4-oxopiperidin-1-ium chloride acetic acid monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-Benzyl-3,5-bis(4-methylbenzylidene)-4-oxopiperidin-1-ium chloride acetic acid monosolvate