Crystal structures of 3,5-bis­[(E)-3-hy­droxy­benzyl­idene]-1-methyl­piperidin-4-one and 3,5-bis­[(E)-2-chloro­benzyl­idene]-1-methyl­piperidin-4-one

Eryanti, Y.; Zamri, A.; Herlina, T.; Supratman, U.; Rosli, M.M.; Fun, H.-K.

doi:10.1107/S2056989015020976

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ISSN: 2056-9890

Volume 71| Part 12| December 2015| Pages 1488-1492

https://doi.org/10.1107/S2056989015020976

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Crystal structures of 3,5-bis[(E)-3-hydroxybenzylidene]-1-methylpiperidin-4-one and 3,5-bis[(E)-2-chlorobenzylidene]-1-methylpiperidin-4-one

Yum Eryanti,^a Adel Zamri,^a Tati Herlina,^b Unang Supratman,^c Mohd Mustaqim Rosli ^d ^* and Hoong-Kun Fun ^d,^e

^aLaboratory of Organic Synthesis, Department of Chemistry, Faculty of Mathematics and Natural Sciences, Riau University, Pekanbaru 26293, Indonesia, ^bDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Padjadjaran University, Jalan Raya Bandung-Sumedang Km 21, Jatinangor 45363, Sumedang, Indonesia, ^cDepartment of Chemistry, Faculty of Mathematics and Narural Sciences, Padjadjaran University, Jalan Raya Bandung-Sumedang Km 21, Jatinangor 45363, Sumedang, Indonesia, ^dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^eDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia
^*Correspondence e-mail: mustaqim@usm.my

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 21 October 2015; accepted 5 November 2015; online 11 November 2015)

The title compounds, C₂₀H₁₉NO₃, (1), and C₂₀H₁₇Cl₂NO, (2), are the 3-hydroxybenzylidene and 2-chlorobenzylidene derivatives, respectively, of curcumin [systematic name: (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione]. The dihedral angles between the benzene rings in each compound are 21.07 (6)° for (1) and 13.4 (3)° for (2). In both compounds, the piperidinone rings adopt a sofa confirmation and the methyl group attached to the N atom is in an equatorial position. In the crystal of (1), two pairs of O—H⋯N and O—H⋯O hydrogen bonds link the molecules, forming chains along [10-1]. The chains are linked via C—H⋯O hydrogen bonds, forming undulating sheets parallel to the ac plane. In the crystal of (2), molecules are linked by weak C—H⋯Cl hydrogen bonds, forming chains along the [204] direction. The chains are linked along the a-axis direction by π–π interactions [inter-centroid distance = 3.779 (4) Å]. For compound (2), the crystal studied was a non-merohedral twin with the refined ratio of the twin components being 0.116 (6):0.886 (6).

Keywords: crystal structure; benzylidene; piperidinone; methylpiperidin-4-one; hydrogen bonding.

CCDC references: 1435229; 1052718

1. Chemical context

Curcumin (diferuloylmethane) is a naturally occurring biologically active compound, isolated from the root of the tumeric plant (Curcuma longa) (Dandia et al., 2012 ). It has been shown to exhibit anti-oxidant (Rostom et al., 2009 ), anti-inflammatory (Suzuki et al., 2005 ), antiviral (Kumar et al., 2007 ) and antibacterial (Bandgar et al., 2012 ) activities, and thus has potential against various malignant cancers, diabetes, allergies, arthritis and other chronic illnesses (Yadav et al., 2010 ; Reddy et al., 2009 ; Aggarwal et al., 2003 ; Insuasty et al., 2013 ; Wu et al., 2013 ). For the purpose of finding new derivatives with increased systemic bioavailability and enhanced pharmacological activity (Zhao et al., 2010 ), chemical modifications as well as the synthesis of curcumin analogues have been attempted by many research groups in order to find a better treatment for various diseases (Siddiqui et al., 2006 ; Gregory et al., 2013 ). Analogous compounds to (E)-3,5-bis(benzylidene)-4-piperidones present noteworthy cytotoxic activity against leukemia cell lines and colon cancer, among others (Gregory et al., 2013). Different substituents were designed to investigate and discuss the structure–activity relationship (Insuasty et al., 2013). Herein, we report on the synthesis, characterization and crystal structures of two mono-carbonyl analogues of curcumin, namely N-methyl-(3E,5E)-3,5-bis(3-hydroxybenzylidene)-4-piperidone (1) and N-methyl-(3E,5E)-3,5-bis(2-chlorobenzylidene)-4-piperidone (2).

2. Structural commentary

The molecular structures of compounds (1) and (2) are shown in Figs. 1 and 2, respectively. Compound (1) crystallized in the triclinic space group P $[\overline{1}]$ (Z = 2), while compound (2) crystallized in the monoclinic space group P2₁/n (Z = 4).

Figure 1
The molecular structure of compound (1), showing 50% probability displacement ellipsoids and the atom labelling.

Figure 2
The molecular structure of compound (2), showing 50% probability displacement ellipsoids and the atom labelling.

The benzene rings (C1–C6 and C14–C19) are inclined to one another by 21.07 (6)° in (1) and by 13.4 (3)° in (2). Both compounds exhibit E conformations about the C7=C8 and C13=C10 bonds. In both compounds, the piperidinone ring (N1/C8–C12) adopts a sofa conformation with atom N1 displaced from the mean plane through the five C atoms (C8–C12) by 0.7052 (10) Å in (1) and 0.705 (5) Å in (2). The puckering parameters for the piperidinone ring conformation in (1) are Q = 0.5280 (12) Å, θ = 55.17 (14)° and φ = 353.08 (17)°, while for (2) they are Q = 0.526 (6) Å, θ = 126.1 (7)° and φ = 182.8 (8)°. In both compounds the methyl group attached to atom N1 is in an equatorial position on the piperidinone ring.

3. Supramolecular features

In the crystal of compound (1), molecules are linked via pairs of O—H⋯N hydrogen bonds, forming inversion dimers enclosing an R₂²(18) ring motif (Table 1 and Fig. 3). These dimers are linked by pairs of O—H⋯O hydrogen bonds, enclosing an R₂²(18) ring motif, forming chains along [10 $[\overline{1}]$ ] (Table 1 and Fig. 4). The chains are linked via pairs of C—H⋯O hydrogen bonds (Table 1 and Fig. 4), forming undulating sheets lying parallel to the ac plane (Fig. 5).

Table 1
Hydrogen-bond geometry (Å, °) for (1)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1ⁱ	0.96 (2)	1.81 (2)	2.7278 (14)	160 (2)
O3—H1O3⋯O2ⁱⁱ	0.88 (2)	1.87 (2)	2.7359 (15)	171 (2)
C17—H17A⋯O3ⁱⁱⁱ	0.95	2.51	3.4032 (16)	157
Symmetry codes: (i) -x+2, -y, -z; (ii) -x+1, -y, -z+1; (iii) -x+1, -y+1, -z+2.

Figure 3
An inversion dimer found in compound (1), formed by O—H⋯N hydrogen bonds (dashed lines; see Table 1

Figure 4
Inversion dimers found in compound (1), formed by O—H⋯O and C—H⋯N hydrogen bonds (dashed lines; see Table 1

Figure 5
The crystal packing of compound (1), viewed along the a axis. Dashed lines indicate hydrogen bonds (see Table 1

). H atoms not involved in the hydrogen bonding have been omitted for clarity.

In the crystal of compound (2), molecules are linked by a weak C4—H4A⋯Cl2ⁱ hydrogen bond, forming zigzag chains along [204] (Table 2 and Fig. 6). The chains are linked along the a-axis direction by π–π interactions [Cg2⋯Cg3ⁱ = 3.779 (4) Å, where Cg2 and Cg3 are the centroids of rings C1–C6 and C14–C19, respectively; symmetry code: (i) − x + 1, −y, −z].

Table 2
Hydrogen-bond geometry (Å, °) for (2)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯Cl2ⁱ	0.95	2.85	3.587 (7)	135
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Figure 6
A view along the a axis of the crystal packing of compound (2), showing a zigzag chain formed by weak C—H⋯Cl hydrogen bonds (dashed lines; see Table 2

). H atoms not involved in the hydrogen bonding have been omitted for clarity.

4. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.36, last update February 2015; Groom & Allen, 2014 ) of substructure (3E,5E)-3,5-dibenzylidene-1-methylpiperidin-4-one gave 49 hits. One compound, 3,5-bis(4-chlorobenzylidene)-1-methylpiperidin-4-one, is the 4-chlorobenzylidene isomer of compound (2) (UNOXOL; Nesterov et al., 2011 ). Here, the benzene rings are inclined to one another by 7.58 (8)°, compared to 21.07 (6)° in (1) and 13.4 (3)° in (2). The piperidinone ring also adopts a sofa conformation with the N atom displaced from the mean plane of the five C atoms by 0.7714 (15) Å, compared to 0.7052 (10) Å in (1) and 0.705 (5) Å in (2).

5. Synthesis and crystallization

Both compounds were synthesized according to a partially modified procedure of a previous report (Gregory et al., 2013).

Compound (1): The corresponding N-methyl-4-piperidone (0.99 g, 0.01 mol), 3-hydroxybenzaldehyde (2.23 g, 0.02 mol), 40% aq. NaOH (0.7 ml) and 95% EtOH (5 ml) were mixed with stirring at room temperature for 30 min. The reaction mixture was subjected to microwave irradiation for 3 min at a power of 180 W and temperature of 333 K. The reaction product was cooled and cold water was added. The precipitate formed was filtered and recrystallized from a mixture of n-hexane–ethyl acetate to afford dark yellowish crystals of compound (1) (yield: 3.4 g, 34.5%; m.p. 409–410 K). R_f = 0.43 (n-hexane:EtOAc = 1:1). UV (MeOH) λ_max: 364 nm (∊ 4,600). IR (KBr) ν_max cm⁻¹: 3400, 1658, 1600 and 1504 cm⁻¹. ¹H NMR (500 MHz, CDCl3): δ (p.p.m.) 8.04 (2H, s), 7.31 (2H, d, J = 7.5 Hz), 7.26 (2H, t, J = 7.5 Hz), 6.99 (2H, d, J = 8.0 Hz), 6.93 (2H, t, J = 7.5 Hz), 3.72 (4H, s) and 2.41 (3H, s). ¹³C NMR (125 MHz, CDCl3): δ (p.p.m.) 185.9, 156.6, 133.2, 130.7, 130.5, 130.3, 122.6, 119.4, 115.7, 57.2, 45.2. HR–ESI–TOFMS: calculated for C₂₀H₁₉NO₃ [M + H]⁺, m/z 321.1365, found m/z 322.1434.

Compound (2): The corresponding N-methyl-4-piperidone (0.98 g, 0.01 mol), 2-chlorobenzaldehyde (2.20 g, 0.02 mol), 40% aq. NaOH (0.7 ml) and 95% EtOH (5 ml) was stirred at room temperature for 30 min. The reaction mixture was subjected to microwave irradiation for 3 min at a power of 180 W and temperature of 333 K. The reaction product was cooled and cold water was added. The precipitate formed was filtered and recrystallized from a mixture of n-hexane–ethyl acetate to afford yellowish crystals of compound (2) (yield: 3.8 g, 38.4%; m.p. 408–410 K). R_f = 0.60 (CH₂Cl₂:MeOH = 9.5:0.5). UV (MeOH) λ_max: 309 nm (∊ 4,400). IR (KBr) ν_max cm⁻¹: 3328, 1640 cm⁻¹. ¹H NMR (500 MHz, CDCl3): δ (p.p.m.) 8.00 (2H, s), 7.46 (2H, dd, J = 8.0, 1.5 Hz), 7.31 (2H, dd, J = 8.0, 1.5 Hz), 7.30 (2H, d, J = 7.5 Hz), 7.24 (2H, dd, J = 7.5, 1.5 Hz), 3.61 (4H, s), 2.37 (3H, s). ¹³C NMR (125 MHz, CDCl3): δ (p.p.m.) 186.1, 135.2, 134.3, 134.0, 133.6, 130.3, 130.0, 129.9, 126.4, 56.7, 45.5. HR–ESI–TOFMS: calculated for C₂₀H₁₇Cl₂NO [M + H]⁺, m/z 357.0687, found m/z 358.0776.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The O-bound H atoms were located in difference Fourier maps and freely refined. The remaining H atoms were positioned geometrically and refined using a riding model: C—H = 0.95–0.99 Å with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other H atoms. A rotating group model was applied to the methyl groups. For compound (2) the crystal studied was a non-merohedral twin with a ratio of the twin components of 0.116 (6):0.886 (6).

Table 3
Experimental details

	(1)	(2)
Crystal data
Chemical formula	C₂₀H₁₉NO₃	C₂₀H₁₇Cl₂NO
M_r	321.36	358.24
Crystal system, space group	Triclinic, P $[\overline{1}]$	Monoclinic, P2₁/n
Temperature (K)	100	100
a, b, c (Å)	7.4852 (6), 9.8588 (9), 11.6115 (10)	7.540 (3), 10.623 (4), 21.119 (7)
α, β, γ (°)	111.7924 (17), 96.7983 (18), 92.8848 (17)	90, 98.671 (5), 90
V (Å³)	785.90 (12)	1672.2 (10)
Z	2	4
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	0.09	0.39
Crystal size (mm)	0.29 × 0.24 × 0.11	0.32 × 0.08 × 0.08

Data collection
Diffractometer	Bruker APEX DUO CCD area detector	Bruker APEX DUO CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )	Multi-scan (SADABS; Bruker, 2009)
No. of measured, independent and observed [I > 2σ(I)] reflections	10462, 3562, 3133	3105, 3105, 2591
R_int	0.021	0.084
(sin θ/λ)_max (Å⁻¹)	0.650	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.117, 1.04	0.077, 0.192, 1.18
No. of reflections	3562	3105
No. of parameters	226	218
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.21	0.45, −0.43
Computer programs: APEX2 and SAINT (Bruker, 2009), SHELXS and SHELXTL (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC references: 1435229; 1052718

Crystal structure: contains datablocks 1, 2, global. DOI: https://doi.org/10.1107/S2056989015020976/su5232sup1.cif

Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2056989015020976/su52321sup4.hkl

Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2056989015020976/su52322sup5.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015020976/su52321sup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989015020976/su52322sup5.cml

checkCIF report

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(1) 3,5-Bis[(E)-3-hydroxybenzylidene]-1-methylpiperidin-4-one top

Crystal data top

C₂₀H₁₉NO₃	Z = 2
M_r = 321.36	F(000) = 340
Triclinic, P1	D_x = 1.358 Mg m⁻³
a = 7.4852 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8588 (9) Å	Cell parameters from 3138 reflections
c = 11.6115 (10) Å	θ = 2.8–32.1°
α = 111.7924 (17)°	µ = 0.09 mm⁻¹
β = 96.7983 (18)°	T = 100 K
γ = 92.8848 (17)°	Block, orange
V = 785.90 (12) Å³	0.29 × 0.24 × 0.11 mm

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	3133 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.021
φ and ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
	k = −12→12
10462 measured reflections	l = −15→15
3562 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0694P)² + 0.2741P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3562 reflections	Δρ_max = 0.37 e Å⁻³
226 parameters	Δρ_min = −0.21 e Å⁻³

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	1.16705 (13)	−0.33469 (10)	−0.27862 (8)	0.0217 (2)
O2	0.78550 (12)	−0.06971 (10)	0.30379 (9)	0.0219 (2)
O3	0.36575 (12)	0.35383 (10)	0.81746 (9)	0.0197 (2)
N1	1.15110 (13)	0.28041 (10)	0.38630 (9)	0.0139 (2)
C1	1.36371 (16)	−0.10777 (13)	0.09923 (11)	0.0159 (2)
H1A	1.4117	−0.0550	0.1849	0.019*
C2	1.47889 (17)	−0.16263 (13)	0.01131 (12)	0.0182 (3)
H2A	1.6059	−0.1478	0.0376	0.022*
C3	1.41151 (17)	−0.23866 (13)	−0.11397 (12)	0.0184 (3)
H3A	1.4922	−0.2770	−0.1728	0.022*
C4	1.22557 (17)	−0.25933 (13)	−0.15432 (11)	0.0159 (3)
C5	1.10880 (16)	−0.20577 (12)	−0.06675 (11)	0.0145 (2)
H5A	0.9819	−0.2202	−0.0936	0.017*
C6	1.17643 (16)	−0.13047 (12)	0.06113 (11)	0.0137 (2)
C7	1.04624 (16)	−0.09053 (12)	0.14976 (11)	0.0141 (2)
H7A	0.9348	−0.1514	0.1238	0.017*
C8	1.06141 (16)	0.02010 (12)	0.26281 (11)	0.0136 (2)
C9	0.91333 (16)	0.02744 (13)	0.33844 (11)	0.0152 (2)
C10	0.92406 (16)	0.15518 (12)	0.45975 (11)	0.0139 (2)
C11	1.08023 (16)	0.27250 (12)	0.49664 (11)	0.0144 (2)
H11A	1.0401	0.3687	0.5454	0.017*
H11B	1.1779	0.2515	0.5511	0.017*
C12	1.21650 (16)	0.13979 (12)	0.31593 (11)	0.0148 (2)
H12A	1.3070	0.1144	0.3721	0.018*
H12B	1.2760	0.1484	0.2468	0.018*
C13	0.78975 (16)	0.15721 (12)	0.52792 (11)	0.0145 (2)
H13A	0.7002	0.0755	0.4914	0.017*
C14	0.75909 (16)	0.26419 (12)	0.64853 (11)	0.0136 (2)
C15	0.58209 (16)	0.25978 (12)	0.67642 (11)	0.0143 (2)
H15A	0.4913	0.1888	0.6179	0.017*
C16	0.53717 (16)	0.35752 (12)	0.78829 (11)	0.0150 (2)
C17	0.66948 (17)	0.46108 (13)	0.87504 (11)	0.0173 (3)
H17A	0.6396	0.5296	0.9509	0.021*
C18	0.84563 (17)	0.46288 (13)	0.84920 (11)	0.0165 (3)
H18A	0.9366	0.5320	0.9093	0.020*
C19	0.89262 (16)	0.36657 (13)	0.73795 (11)	0.0154 (2)
H19A	1.0142	0.3699	0.7224	0.018*
C20	1.29894 (17)	0.39929 (13)	0.42690 (12)	0.0183 (3)
H20A	1.2574	0.4907	0.4814	0.027*
H20B	1.3364	0.4123	0.3533	0.027*
H20C	1.4017	0.3742	0.4731	0.027*
H1O1	1.044 (3)	−0.321 (2)	−0.302 (2)	0.049 (6)*
H1O3	0.311 (3)	0.266 (2)	0.7732 (18)	0.038 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0232 (5)	0.0259 (5)	0.0132 (4)	0.0063 (4)	0.0045 (4)	0.0032 (4)
O2	0.0192 (5)	0.0202 (4)	0.0187 (5)	−0.0078 (3)	0.0065 (4)	−0.0011 (4)
O3	0.0171 (4)	0.0197 (4)	0.0178 (5)	−0.0004 (3)	0.0076 (3)	0.0008 (4)
N1	0.0144 (5)	0.0132 (4)	0.0126 (5)	−0.0025 (4)	0.0037 (4)	0.0030 (4)
C1	0.0172 (6)	0.0146 (5)	0.0154 (6)	0.0012 (4)	0.0019 (4)	0.0055 (4)
C2	0.0142 (6)	0.0200 (6)	0.0225 (6)	0.0028 (4)	0.0044 (5)	0.0100 (5)
C3	0.0185 (6)	0.0192 (6)	0.0198 (6)	0.0053 (5)	0.0085 (5)	0.0079 (5)
C4	0.0210 (6)	0.0139 (5)	0.0132 (6)	0.0029 (4)	0.0044 (5)	0.0047 (4)
C5	0.0142 (5)	0.0140 (5)	0.0157 (6)	0.0014 (4)	0.0035 (4)	0.0058 (4)
C6	0.0158 (6)	0.0109 (5)	0.0151 (6)	0.0014 (4)	0.0044 (4)	0.0053 (4)
C7	0.0136 (5)	0.0147 (5)	0.0141 (6)	−0.0003 (4)	0.0021 (4)	0.0058 (4)
C8	0.0129 (5)	0.0137 (5)	0.0142 (6)	0.0008 (4)	0.0025 (4)	0.0053 (4)
C9	0.0147 (6)	0.0152 (5)	0.0151 (6)	0.0001 (4)	0.0029 (4)	0.0049 (4)
C10	0.0138 (5)	0.0141 (5)	0.0126 (5)	−0.0005 (4)	0.0015 (4)	0.0042 (4)
C11	0.0148 (6)	0.0151 (5)	0.0116 (5)	−0.0017 (4)	0.0029 (4)	0.0031 (4)
C12	0.0137 (5)	0.0148 (5)	0.0147 (6)	−0.0007 (4)	0.0043 (4)	0.0037 (4)
C13	0.0142 (5)	0.0140 (5)	0.0137 (6)	−0.0012 (4)	0.0014 (4)	0.0039 (4)
C14	0.0155 (6)	0.0136 (5)	0.0124 (5)	0.0009 (4)	0.0029 (4)	0.0056 (4)
C15	0.0153 (6)	0.0142 (5)	0.0118 (5)	−0.0013 (4)	0.0019 (4)	0.0036 (4)
C16	0.0153 (6)	0.0151 (5)	0.0152 (6)	0.0017 (4)	0.0045 (4)	0.0058 (4)
C17	0.0230 (6)	0.0145 (5)	0.0130 (6)	0.0006 (5)	0.0044 (5)	0.0035 (4)
C18	0.0191 (6)	0.0149 (5)	0.0138 (6)	−0.0036 (4)	−0.0004 (4)	0.0052 (4)
C19	0.0146 (6)	0.0175 (5)	0.0146 (6)	−0.0008 (4)	0.0022 (4)	0.0070 (5)
C20	0.0183 (6)	0.0153 (5)	0.0188 (6)	−0.0044 (4)	0.0047 (5)	0.0039 (5)

Geometric parameters (Å, º) top

O1—C4	1.3596 (15)	C9—C10	1.4908 (16)
O1—H1O1	0.96 (2)	C10—C13	1.3476 (16)
O2—C9	1.2351 (14)	C10—C11	1.5051 (15)
O3—C16	1.3674 (14)	C11—H11A	0.9900
O3—H1O3	0.87 (2)	C11—H11B	0.9900
N1—C12	1.4668 (15)	C12—H12A	0.9900
N1—C20	1.4684 (14)	C12—H12B	0.9900
N1—C11	1.4697 (15)	C13—C14	1.4595 (16)
C1—C2	1.3868 (17)	C13—H13A	0.9500
C1—C6	1.3996 (17)	C14—C15	1.4030 (16)
C1—H1A	0.9500	C14—C19	1.4038 (16)
C2—C3	1.3824 (18)	C15—C16	1.3912 (16)
C2—H2A	0.9500	C15—H15A	0.9500
C3—C4	1.3944 (18)	C16—C17	1.3915 (17)
C3—H3A	0.9500	C17—C18	1.3871 (17)
C4—C5	1.3910 (16)	C17—H17A	0.9500
C5—C6	1.4064 (16)	C18—C19	1.3872 (17)
C5—H5A	0.9500	C18—H18A	0.9500
C6—C7	1.4625 (16)	C19—H19A	0.9500
C7—C8	1.3472 (16)	C20—H20A	0.9800
C7—H7A	0.9500	C20—H20B	0.9800
C8—C9	1.4819 (16)	C20—H20C	0.9800
C8—C12	1.5076 (15)

C4—O1—H1O1	112.0 (13)	C10—C11—H11A	109.3
C16—O3—H1O3	108.1 (12)	N1—C11—H11B	109.3
C12—N1—C20	110.15 (9)	C10—C11—H11B	109.3
C12—N1—C11	109.61 (9)	H11A—C11—H11B	108.0
C20—N1—C11	109.52 (9)	N1—C12—C8	110.31 (9)
C2—C1—C6	119.72 (11)	N1—C12—H12A	109.6
C2—C1—H1A	120.1	C8—C12—H12A	109.6
C6—C1—H1A	120.1	N1—C12—H12B	109.6
C3—C2—C1	120.94 (11)	C8—C12—H12B	109.6
C3—C2—H2A	119.5	H12A—C12—H12B	108.1
C1—C2—H2A	119.5	C10—C13—C14	130.67 (11)
C2—C3—C4	120.23 (11)	C10—C13—H13A	114.7
C2—C3—H3A	119.9	C14—C13—H13A	114.7
C4—C3—H3A	119.9	C15—C14—C19	118.59 (11)
O1—C4—C5	123.05 (11)	C15—C14—C13	116.26 (10)
O1—C4—C3	117.67 (11)	C19—C14—C13	125.13 (11)
C5—C4—C3	119.27 (11)	C16—C15—C14	121.15 (11)
C4—C5—C6	120.74 (11)	C16—C15—H15A	119.4
C4—C5—H5A	119.6	C14—C15—H15A	119.4
C6—C5—H5A	119.6	O3—C16—C15	121.89 (11)
C1—C6—C5	119.07 (11)	O3—C16—C17	118.25 (11)
C1—C6—C7	122.82 (11)	C15—C16—C17	119.85 (11)
C5—C6—C7	117.90 (10)	C18—C17—C16	119.08 (11)
C8—C7—C6	129.38 (11)	C18—C17—H17A	120.5
C8—C7—H7A	115.3	C16—C17—H17A	120.5
C6—C7—H7A	115.3	C17—C18—C19	121.80 (11)
C7—C8—C9	117.96 (10)	C17—C18—H18A	119.1
C7—C8—C12	124.30 (10)	C19—C18—H18A	119.1
C9—C8—C12	117.72 (10)	C18—C19—C14	119.49 (11)
O2—C9—C8	121.55 (11)	C18—C19—H19A	120.3
O2—C9—C10	120.44 (11)	C14—C19—H19A	120.3
C8—C9—C10	118.00 (10)	N1—C20—H20A	109.5
C13—C10—C9	116.70 (10)	N1—C20—H20B	109.5
C13—C10—C11	124.79 (10)	H20A—C20—H20B	109.5
C9—C10—C11	118.51 (10)	N1—C20—H20C	109.5
N1—C11—C10	111.60 (9)	H20A—C20—H20C	109.5
N1—C11—H11A	109.3	H20B—C20—H20C	109.5

C6—C1—C2—C3	0.52 (18)	C12—N1—C11—C10	−60.87 (12)
C1—C2—C3—C4	1.06 (18)	C20—N1—C11—C10	178.18 (10)
C2—C3—C4—O1	179.88 (11)	C13—C10—C11—N1	−152.54 (12)
C2—C3—C4—C5	−1.56 (18)	C9—C10—C11—N1	26.59 (15)
O1—C4—C5—C6	178.98 (11)	C20—N1—C12—C8	−174.22 (9)
C3—C4—C5—C6	0.50 (17)	C11—N1—C12—C8	65.22 (12)
C2—C1—C6—C5	−1.56 (17)	C7—C8—C12—N1	142.85 (12)
C2—C1—C6—C7	172.99 (11)	C9—C8—C12—N1	−35.19 (14)
C4—C5—C6—C1	1.06 (17)	C9—C10—C13—C14	−179.80 (12)
C4—C5—C6—C7	−173.76 (10)	C11—C10—C13—C14	−0.7 (2)
C1—C6—C7—C8	31.69 (19)	C10—C13—C14—C15	160.79 (13)
C5—C6—C7—C8	−153.70 (12)	C10—C13—C14—C19	−20.9 (2)
C6—C7—C8—C9	−174.71 (11)	C19—C14—C15—C16	2.09 (18)
C6—C7—C8—C12	7.3 (2)	C13—C14—C15—C16	−179.43 (11)
C7—C8—C9—O2	4.94 (18)	C14—C15—C16—O3	−179.37 (11)
C12—C8—C9—O2	−176.91 (11)	C14—C15—C16—C17	−0.52 (18)
C7—C8—C9—C10	−176.05 (11)	O3—C16—C17—C18	177.59 (11)
C12—C8—C9—C10	2.11 (16)	C15—C16—C17—C18	−1.30 (18)
O2—C9—C10—C13	0.53 (18)	C16—C17—C18—C19	1.55 (19)
C8—C9—C10—C13	−178.49 (11)	C17—C18—C19—C14	0.05 (18)
O2—C9—C10—C11	−178.66 (11)	C15—C14—C19—C18	−1.85 (17)
C8—C9—C10—C11	2.31 (17)	C13—C14—C19—C18	179.83 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1ⁱ	0.96 (2)	1.81 (2)	2.7278 (14)	160 (2)
O3—H1O3···O2ⁱⁱ	0.88 (2)	1.87 (2)	2.7359 (15)	171 (2)
C17—H17A···O3ⁱⁱⁱ	0.95	2.51	3.4032 (16)	157

Symmetry codes: (i) −x+2, −y, −z; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+2.

(2) 3,5-Bis[(E)-2-chlorobenzylidene]-1-methylpiperidin-4-one top

Crystal data top

C₂₀H₁₇Cl₂NO	F(000) = 744
M_r = 358.24	D_x = 1.423 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.540 (3) Å	Cell parameters from 3908 reflections
b = 10.623 (4) Å	θ = 2.7–29.2°
c = 21.119 (7) Å	µ = 0.39 mm⁻¹
β = 98.671 (5)°	T = 100 K
V = 1672.2 (10) Å³	Needle, yellow
Z = 4	0.32 × 0.08 × 0.08 mm

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	2591 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.084
φ and ω scans	θ_max = 25.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
	k = −12→12
3105 measured reflections	l = −5→25
3105 independent 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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.192	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + 13.4429P] where P = (F_o² + 2F_c²)/3
3105 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.8841 (2)	0.46525 (14)	0.06491 (7)	0.0261 (4)
Cl2	0.6925 (2)	−0.18217 (14)	−0.22186 (7)	0.0242 (4)
O1	0.6046 (5)	0.0962 (4)	−0.04698 (18)	0.0193 (9)
N1	0.9749 (6)	−0.1131 (4)	0.0667 (2)	0.0179 (10)
C1	0.7905 (8)	0.1999 (6)	0.1897 (3)	0.0205 (13)
H1A	0.7492	0.1153	0.1892	0.025*
C2	0.8325 (8)	0.2615 (6)	0.2487 (3)	0.0244 (13)
H2A	0.8193	0.2199	0.2876	0.029*
C3	0.8940 (8)	0.3854 (6)	0.2491 (3)	0.0263 (14)
H3A	0.9266	0.4275	0.2889	0.032*
C4	0.9085 (8)	0.4479 (6)	0.1928 (3)	0.0264 (14)
H4A	0.9477	0.5329	0.1934	0.032*
C5	0.8648 (8)	0.3841 (5)	0.1355 (3)	0.0182 (12)
C6	0.8072 (7)	0.2581 (5)	0.1317 (3)	0.0178 (12)
C7	0.7554 (7)	0.1956 (5)	0.0699 (3)	0.0184 (12)
H7A	0.6965	0.2461	0.0359	0.022*
C8	0.7825 (7)	0.0744 (5)	0.0562 (3)	0.0156 (12)
C9	0.7007 (7)	0.0275 (6)	−0.0089 (3)	0.0181 (12)
C10	0.7323 (7)	−0.1071 (5)	−0.0242 (3)	0.0158 (12)
C11	0.8378 (8)	−0.1877 (5)	0.0269 (3)	0.0186 (12)
H11A	0.7555	−0.2250	0.0542	0.022*
H11B	0.8959	−0.2573	0.0066	0.022*
C12	0.8874 (8)	−0.0179 (5)	0.1009 (3)	0.0179 (12)
H12A	0.9794	0.0279	0.1305	0.021*
H12B	0.8056	−0.0598	0.1268	0.021*
C13	0.6595 (7)	−0.1495 (5)	−0.0815 (3)	0.0165 (12)
H13A	0.6044	−0.0878	−0.1106	0.020*
C14	0.6534 (7)	−0.2798 (5)	−0.1058 (3)	0.0161 (12)
C15	0.6583 (7)	−0.3058 (5)	−0.1704 (3)	0.0185 (12)
C16	0.6392 (8)	−0.4257 (6)	−0.1957 (3)	0.0210 (13)
H16A	0.6420	−0.4397	−0.2400	0.025*
C17	0.6158 (8)	−0.5253 (6)	−0.1554 (3)	0.0229 (13)
H17A	0.6032	−0.6084	−0.1721	0.027*
C18	0.6106 (8)	−0.5046 (6)	−0.0912 (3)	0.0210 (13)
H18A	0.5949	−0.5729	−0.0635	0.025*
C19	0.6288 (7)	−0.3818 (5)	−0.0674 (3)	0.0187 (12)
H19A	0.6242	−0.3679	−0.0232	0.022*
C20	1.0862 (8)	−0.1939 (6)	0.1114 (3)	0.0225 (13)
H20A	1.1440	−0.2573	0.0877	0.034*
H20B	1.1783	−0.1432	0.1375	0.034*
H20C	1.0117	−0.2359	0.1393	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0287 (8)	0.0196 (7)	0.0305 (8)	−0.0023 (6)	0.0065 (6)	0.0026 (6)
Cl2	0.0292 (8)	0.0260 (8)	0.0176 (7)	−0.0003 (6)	0.0038 (6)	0.0015 (6)
O1	0.020 (2)	0.018 (2)	0.019 (2)	0.0055 (17)	0.0001 (17)	0.0049 (17)
N1	0.012 (2)	0.019 (3)	0.022 (2)	0.002 (2)	0.000 (2)	−0.002 (2)
C1	0.019 (3)	0.020 (3)	0.023 (3)	0.003 (2)	0.005 (2)	−0.002 (2)
C2	0.019 (3)	0.027 (3)	0.027 (3)	0.006 (3)	0.002 (3)	−0.002 (3)
C3	0.023 (3)	0.029 (4)	0.027 (3)	0.007 (3)	0.002 (3)	−0.012 (3)
C4	0.021 (3)	0.023 (3)	0.035 (4)	0.001 (3)	0.001 (3)	−0.005 (3)
C5	0.016 (3)	0.015 (3)	0.023 (3)	0.001 (2)	0.003 (2)	0.004 (2)
C6	0.012 (3)	0.018 (3)	0.023 (3)	0.003 (2)	0.004 (2)	−0.003 (2)
C7	0.014 (3)	0.019 (3)	0.023 (3)	0.001 (2)	0.005 (2)	0.004 (2)
C8	0.015 (3)	0.015 (3)	0.019 (3)	0.000 (2)	0.007 (2)	−0.002 (2)
C9	0.013 (3)	0.025 (3)	0.018 (3)	−0.004 (2)	0.007 (2)	0.000 (2)
C10	0.013 (3)	0.018 (3)	0.017 (3)	0.003 (2)	0.006 (2)	0.004 (2)
C11	0.020 (3)	0.017 (3)	0.019 (3)	0.000 (2)	0.003 (2)	−0.003 (2)
C12	0.019 (3)	0.017 (3)	0.018 (3)	0.000 (2)	0.004 (2)	−0.005 (2)
C13	0.016 (3)	0.019 (3)	0.014 (3)	0.000 (2)	0.002 (2)	0.000 (2)
C14	0.011 (3)	0.020 (3)	0.017 (3)	0.002 (2)	0.002 (2)	−0.001 (2)
C15	0.015 (3)	0.020 (3)	0.020 (3)	0.001 (2)	0.002 (2)	−0.002 (2)
C16	0.020 (3)	0.026 (3)	0.017 (3)	0.000 (3)	0.001 (2)	−0.005 (2)
C17	0.023 (3)	0.018 (3)	0.027 (3)	−0.004 (3)	0.001 (3)	−0.008 (3)
C18	0.018 (3)	0.024 (3)	0.020 (3)	−0.003 (3)	−0.001 (2)	−0.001 (2)
C19	0.016 (3)	0.021 (3)	0.019 (3)	0.001 (2)	0.001 (2)	−0.004 (2)
C20	0.025 (3)	0.020 (3)	0.022 (3)	0.002 (3)	0.001 (3)	0.001 (2)

Geometric parameters (Å, º) top

Cl1—C5	1.747 (6)	C10—C13	1.331 (8)
Cl2—C15	1.749 (6)	C10—C11	1.508 (8)
O1—C9	1.236 (7)	C11—H11A	0.9900
N1—C20	1.447 (7)	C11—H11B	0.9900
N1—C12	1.457 (7)	C12—H12A	0.9900
N1—C11	1.462 (7)	C12—H12B	0.9900
C1—C6	1.396 (8)	C13—C14	1.474 (8)
C1—C2	1.402 (8)	C13—H13A	0.9500
C1—H1A	0.9500	C14—C19	1.383 (8)
C2—C3	1.395 (9)	C14—C15	1.398 (8)
C2—H2A	0.9500	C15—C16	1.381 (8)
C3—C4	1.381 (9)	C16—C17	1.386 (8)
C3—H3A	0.9500	C16—H16A	0.9500
C4—C5	1.382 (8)	C17—C18	1.381 (8)
C4—H4A	0.9500	C17—H17A	0.9500
C5—C6	1.406 (8)	C18—C19	1.397 (8)
C6—C7	1.464 (8)	C18—H18A	0.9500
C7—C8	1.343 (8)	C19—H19A	0.9500
C7—H7A	0.9500	C20—H20A	0.9800
C8—C12	1.501 (8)	C20—H20B	0.9800
C8—C9	1.505 (8)	C20—H20C	0.9800
C9—C10	1.492 (8)

C20—N1—C12	110.4 (4)	N1—C11—H11B	109.5
C20—N1—C11	110.1 (5)	C10—C11—H11B	109.5
C12—N1—C11	109.1 (4)	H11A—C11—H11B	108.1
C6—C1—C2	122.4 (6)	N1—C12—C8	112.1 (4)
C6—C1—H1A	118.8	N1—C12—H12A	109.2
C2—C1—H1A	118.8	C8—C12—H12A	109.2
C3—C2—C1	118.5 (6)	N1—C12—H12B	109.2
C3—C2—H2A	120.8	C8—C12—H12B	109.2
C1—C2—H2A	120.8	H12A—C12—H12B	107.9
C4—C3—C2	121.2 (6)	C10—C13—C14	128.4 (5)
C4—C3—H3A	119.4	C10—C13—H13A	115.8
C2—C3—H3A	119.4	C14—C13—H13A	115.8
C3—C4—C5	118.6 (6)	C19—C14—C15	116.3 (5)
C3—C4—H4A	120.7	C19—C14—C13	122.2 (5)
C5—C4—H4A	120.7	C15—C14—C13	121.4 (5)
C4—C5—C6	123.2 (6)	C16—C15—C14	122.9 (5)
C4—C5—Cl1	117.7 (5)	C16—C15—Cl2	118.0 (4)
C6—C5—Cl1	119.0 (5)	C14—C15—Cl2	119.1 (4)
C1—C6—C5	116.1 (5)	C15—C16—C17	118.8 (5)
C1—C6—C7	122.3 (5)	C15—C16—H16A	120.6
C5—C6—C7	121.5 (5)	C17—C16—H16A	120.6
C8—C7—C6	126.7 (5)	C18—C17—C16	120.4 (6)
C8—C7—H7A	116.6	C18—C17—H17A	119.8
C6—C7—H7A	116.6	C16—C17—H17A	119.8
C7—C8—C12	125.1 (5)	C17—C18—C19	119.1 (6)
C7—C8—C9	117.3 (5)	C17—C18—H18A	120.4
C12—C8—C9	117.6 (5)	C19—C18—H18A	120.4
O1—C9—C10	121.5 (5)	C14—C19—C18	122.4 (5)
O1—C9—C8	121.2 (5)	C14—C19—H19A	118.8
C10—C9—C8	117.2 (5)	C18—C19—H19A	118.8
C13—C10—C9	117.6 (5)	N1—C20—H20A	109.5
C13—C10—C11	124.0 (5)	N1—C20—H20B	109.5
C9—C10—C11	118.3 (5)	H20A—C20—H20B	109.5
N1—C11—C10	110.7 (5)	N1—C20—H20C	109.5
N1—C11—H11A	109.5	H20A—C20—H20C	109.5
C10—C11—H11A	109.5	H20B—C20—H20C	109.5

C6—C1—C2—C3	−0.4 (9)	C20—N1—C11—C10	−174.5 (4)
C1—C2—C3—C4	2.0 (9)	C12—N1—C11—C10	64.2 (6)
C2—C3—C4—C5	−1.6 (9)	C13—C10—C11—N1	149.3 (5)
C3—C4—C5—C6	−0.5 (9)	C9—C10—C11—N1	−33.2 (7)
C3—C4—C5—Cl1	180.0 (5)	C20—N1—C12—C8	175.3 (5)
C2—C1—C6—C5	−1.5 (8)	C11—N1—C12—C8	−63.6 (6)
C2—C1—C6—C7	−177.1 (5)	C7—C8—C12—N1	−149.2 (5)
C4—C5—C6—C1	1.9 (8)	C9—C8—C12—N1	31.0 (7)
Cl1—C5—C6—C1	−178.5 (4)	C9—C10—C13—C14	−172.8 (5)
C4—C5—C6—C7	177.6 (5)	C11—C10—C13—C14	4.8 (9)
Cl1—C5—C6—C7	−2.9 (7)	C10—C13—C14—C19	37.6 (9)
C1—C6—C7—C8	−39.9 (9)	C10—C13—C14—C15	−147.5 (6)
C5—C6—C7—C8	144.7 (6)	C19—C14—C15—C16	0.3 (8)
C6—C7—C8—C12	−5.9 (9)	C13—C14—C15—C16	−175.0 (5)
C6—C7—C8—C9	173.9 (5)	C19—C14—C15—Cl2	−179.0 (4)
C7—C8—C9—O1	−3.8 (8)	C13—C14—C15—Cl2	5.8 (7)
C12—C8—C9—O1	176.1 (5)	C14—C15—C16—C17	−0.6 (9)
C7—C8—C9—C10	179.6 (5)	Cl2—C15—C16—C17	178.6 (4)
C12—C8—C9—C10	−0.6 (7)	C15—C16—C17—C18	0.4 (9)
O1—C9—C10—C13	2.9 (8)	C16—C17—C18—C19	0.2 (9)
C8—C9—C10—C13	179.6 (5)	C15—C14—C19—C18	0.3 (8)
O1—C9—C10—C11	−174.7 (5)	C13—C14—C19—C18	175.5 (5)
C8—C9—C10—C11	1.9 (7)	C17—C18—C19—C14	−0.5 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···Cl2ⁱ	0.95	2.85	3.587 (7)	135

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Acknowledgements

The authors are grateful to the Ministry of Education and Culture of Indonesia for financial support (research grant No. 2013 for YE) and the Universiti Sains Malaysia for the X-ray measurements.

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Volume 71| Part 12| December 2015| Pages 1488-1492

https://doi.org/10.1107/S2056989015020976

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structures of 3,5-bis­­[(E)-3-hy­dr­oxy­benzyl­­idene]-1-methyl­piperidin-4-one and 3,5-bis­­[(E)-2-chloro­benzyl­­idene]-1-methyl­piperidin-4-one

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

References

research communications

Crystal structures of 3,5-bis[(E)-3-hydroxybenzylidene]-1-methylpiperidin-4-one and 3,5-bis[(E)-2-chlorobenzylidene]-1-methylpiperidin-4-one

3. Supramolecular features