Crystal structure and Hirshfeld surface analysis of (2E,2′E)-1,1′-[seleno­bis­(4,1-phenyl­ene)]bis­[3-(4-chloro­phen­yl)prop-2-en-1-one]

Bouraoui, H.; Mechehoud, Y.; Chetioui, S.; Touzani, R.; Medjani, M.; Benmilat, A.; Boudjada, A.

doi:10.1107/S2056989019014038

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ISSN: 2056-9890

Volume 75| Part 11| November 2019| Pages 1724-1728

https://doi.org/10.1107/S2056989019014038

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Crystal structure and Hirshfeld surface analysis of (2E,2′E)-1,1′-[selenobis(4,1-phenylene)]bis[3-(4-chlorophenyl)prop-2-en-1-one]

Hazem Bouraoui,^a,^b Youcef Mechehoud,^c Souheyla Chetioui,^d,^e ^* Rachid Touzani,^f,^g ^* Meriem Medjani,^a Ahmed Benmilat ^a and Ali Boudjada ^a

^aLaboratoire de Cristallographie, Département de Physique, Université des Frères Mentouri-Constantine, 25000 Constantine, Algeria, ^bUniversité de Ouargla, Faculté des Mathématiques et Sciences de la Matiére, Route de Ghardaia, Ouargla 30000, Algeria, ^cLaboratoire VAREN, Département de Chimie, Faculté des Sciences Exactes, Université Mentouri-Constantine, 25000 Constantine, Algeria, ^dUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université des Frères Mentouri Constantine, Constantine 25000, Algeria, ^eFaculté de Technologie, Université Mohamed Boudiaf, M'sila, Algeria, ^fLaboratoire de Chimie Appliquée et Environnement, LCAE-URAC18, COSTE, Faculté des Sciences, Université Mohamed Premier, BP524, 60000, Oujda, Morocco, and ^gFaculté Pluridisciplinaire Nador BP 300, Selouane 62702, Nador, Morocco
^*Correspondence e-mail: souheilachetioui@yahoo.fr, touzanir@yahoo.fr

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 9 September 2019; accepted 15 October 2019; online 22 October 2019)

In the title compound, C₃₀H₂₀Cl₂O₂Se, the C—Se—C angle is 99.0 (2)°, with the dihedral angle between the planes of the attached benzene rings being 79.1 (3)°. The average endocyclic angles (Se—C—C) facing the Se atom are 122.1 (5) and 122.2 (5)°. The Se atom is essentially coplanar with the attached benzene rings, deviating by 0.075 (1) and 0.091 (1) Å. In the two phenylene(4-chlorophenyl)prop-2-en-1-one units, the benzene rings are inclined to each other by 44.6 (3) and 7.8 (3)°. In the crystal, the molecules stack up the a axis, forming layers parallel to the ac plane. There are no significant classical intermolecular interactions present. Hirshfeld surface analysis, two-dimensional fingerprint plots and the molecular electrostatic potential surface were used to analyse the crystal packing. The Hirshfeld surface analysis suggests that the most significant contributions to the crystal packing are by C⋯H/H⋯C contacts (17.7%).

Keywords: crystal structure; organoselenium; selenium; Hirshfeld surface analysis.

CCDC references: 1959404; 1959404

1. Chemical context

During the last few years, organoselenium chemistry (Procter, 2001 ) has been the subject of constant scientific interest and organoselenium compounds have been used intensively as important reagents and intermediates in organic synthesis (Zade et al., 2005 ). Recently, various organoselenium compounds have attracted growing attention in medicine. Selenoproteins are very important for neuronal survival and function. It has been found that selenoprotein P may influence Alzheimer pathology (Bellinger et al., 2008 ). Furthermore, the potential of selenoproteins to protect against oxidative stress led to the expectation that selenium would be protective against type 2 diabetes, and indeed in the 1990s, selenium was shown to have antidiabetic and insulin mimetic effects (Steinbrenner et al., 2011 ). However, more recently, findings from observational epidemiological studies and randomized clinical trials have raised concern that high selenium exposure may lead to type 2 diabetes or insulin resistance at least in well-nourished populations (Stranges et al., 2010 ). In addition, molecules involving selenium are still efficient and encouraged in medicinal chemistry (Zhao et al., 2012 ). Moreover, organoselenium compounds are of considerable interest in academia, as anticancer (Zhu & Jiang, 2008 ), anti-oxidant (Anderson et al., 1996 ), anti-inflammatory and antiallergic agents (Abdel-Hafez, 2008 ), and in industry because of their involvement as key intermediates in the synthesis of pharmaceuticals (Woods et al., 1993 ), fine chemicals and polymers (Hellberg et al., 1997 ). Moreover, chalcone derivatives are notable for their excellent blue-light transmittance and good crystallizability; they also show considerable promise as organic nonlinear optical materials (Uchida et al., 1998 ). In continuation of our work on chalcone organoselenium derivatives, we report herein on the crystal structure of (2E,2′E)-1,1′-[selenobis(4,1-phenylene)]bis[3-(4-chlorophenyl)prop-2-en-1-one].

2. Structural commentary

The molecular structure of the title compound is shown in Fig. 1. The C1—Se1—C16 angle is 99.0 (2)°, which is close to the value observed in three very similar compounds, viz. 99.47 (10)° in bis(4-nitrophenyl) selenide, where the Se atom lies on a twofold rotation axis (Zuo, 2013 ), 99.59 (14)° in bis(4-acetylphenyl) selenide (Bouraoui et al., 2011 ) and 100.03 (15)° in bis(2-chloroethan-1-one-phenyl) selenide (Bouraoui et al., 2015 ).

Figure 1
The molecular structure of the title compound, with the atom labelling and displacement ellipsoids drawn at the 50% probability level.

In the title compound, inner benzene rings A (atoms C1–C6) and C (C16–C21) (see Scheme) are inclined to each other by 79.1 (3)°. This is similar to the same angle observed for the acetylphenyl derivative, viz. 87.08 (15)°, but considerably different to that observed for the 4-nitrophenyl derivative, viz. 63.76 (10)°.

In each phenylene-(4-chlorophenyl)prop-2-en-1-one unit, the C=C has an E configuration. The C=C bond lengths C8=C9 and C23=C24 are 1.317 (8) and 1.325 (8) Å, respectively, which confirms their double-bond character. Benzene rings A and B (C10–C15) of one unit are inclined to one another by 44.6 (3)°, while rings C and D (C25–C30) of the other unit are almost coplanar, with a dihedral angle of 7.8 (3)°. The outer benzene rings, B and D, are almost normal to one another, with a dihedral angle of 84.4 (3)°.

3. Supramolecular features

In the crystal, molecules stack up the a axis, forming layers parallel to the ac plane (Fig. 2). There are no significant classical intermolecular interactions present (PLATON; Spek, 2009 ). The shortest atom–atom contacts in the crystal (Figs. 3 and 4) are given in Table 1 and are discussed in §4 (Hirshfeld surface analysis).

Table 1
Short contacts (Å) in the crystal of the title compound

Atom 1	Atom 2	Length (Å)	vdW length (Å)
H3	H10ⁱ	2.498	0.098
O2	H19ⁱⁱ	2.632	−0.088
H12	O2ⁱⁱⁱ	2.759	0.039
O1	H3ⁱⁱⁱ	2.770	0.050
O2	H20ⁱⁱ	2.818	0.098
H2	C6ⁱⁱⁱ	2.922	0.022
C3	H4ⁱⁱ	2.943	0.043
H3	C15ⁱ	2.964	0.064
O2	C29ⁱⁱ	3.217	−0.003
O2	C30ⁱⁱ	3.314	0.094
C5	C8ⁱ	3.461	0.061
Se1	C17ⁱ	3.475	−0.125
C20	C23ⁱ	3.480	0.080
Cl2	Cl1^iv	3.549	0.049
Symmetry codes: (i) x − 1, y, z; (ii) x − 1, y + 1, z; (iii) x, y − 1, z; (iv) x − 1, y − 1, z + 1.

Figure 2
A view along the b axis of the crystal packing of the title compound, showing the layer-like structure.

Figure 3
A view of the Hirshfeld surface mapped over d_norm in the colour range −0.0711 to 1.3645 a.u.

Figure 4
A view of the Hirshfeld surface plotted over the calculated electrostatic potential energy in the range −0.0489 to 0.0448 a.u.

4. Hirshfeld surface analysis

Insight into the intermolecular interactions in the crystal were obtained from an analysis of the Hirshfeld surface (Spackman & Jayatilaka, 2009 ) and the two-dimensional fingerprint plots (McKinnon et al., 2007 ). The program CrystalExplorer (Turner et al., 2017 ) was used to generate both the Hirshfeld surfaces, mapped over d_norm, and the electrostatic potential for the title compound. The function d_norm is a ratio enclosing the distances of any surface point to the nearest interior (d_i) and exterior (d_e) atom and the van der Waals (vdW) radii of the atoms. The function d_norm will be equal to zero when intermolecular distances are close to the van der Waals contacts. They are indicated by a white colour on the Hirshfeld surface, while contacts longer than the sum of the vdW radii with positive d_norm values are coloured blue.

The analysis of the Hirshfeld surface (HS) mapped over d_norm is shown in Fig. 4. The H⋯O contacts between the corresponding donor and acceptor atoms are visualized as bright-red spots on the side (zone 4) of the Hirshfeld surface (Fig. 4). Three other red spots exist, corresponding to the C⋯Se, Cl⋯Cl and C⋯O contacts, viz. zones 1, 2 and 3, respectively (Fig. 4). These contacts are considered to be the strongest when comparing them to the sum of the vdW radii [Table 1; calculated using Mercury (Macrae et al., 2008 )].

A view of the molecular electrostatic potential using the 6-31G(d) basis set with the density functional theory (DFT) method for the title compound is shown in Fig. 5. The H⋯O donors and acceptors are shown as blue and red areas around the atoms related with positive (hydrogen-bond donors) and negative (hydrogen-bond acceptors) electrostatic potentials, respectively.

Figure 5
Hirshfeld surface mapped over d_norm to visualize some of the short intermolecular contacts in the crystal (see Table 1

The full two-dimensional fingerprint plot for the title compound is given in Fig. 6(a). Those for the most significant contacts contributing to the HS are given in Fig. 6(b) for H⋯H, Fig. 6(c) for C⋯H/H⋯C, Fig. 6(d) for O⋯H/H⋯O, Fig. 6(e) for Cl⋯H/H⋯Cl and Fig. 6(f) for C⋯C. A full list of the relative percentage contributions of the close contacts to the HS of the title compound are given in Table 2.

Table 2
Relative percentage contributions of the close contacts to the Hirshfeld surface of the title compound

Contact	Percentage contribution
H⋯H	36.0
C⋯H/H⋯C	17.7
O⋯H/H⋯O	11.5
Cl⋯H/H⋯Cl	11.0
C⋯C	10.5
C⋯Cl	4.3
C⋯Se	3.5
Se⋯H/H⋯Se	2.8
Cl⋯Cl	2.4
C⋯O	0.3

Figure 6
(a) The full two-dimensional fingerprint plot for the title compound and those delineated into (b) H⋯H, (c) C⋯H/H⋯C, (d) O⋯H/H⋯O, (e) Cl⋯H/H⋯Cl and (f) C⋯C contacts.

A contribution of 36.0% was found for the H⋯H contacts (Fig. 6b), representing the largest contribution, and is displayed on the fingerprint plots by a pair of very short spikes at d_e + d_i = 2.3 Å; the vdW radius for this interaction is 2.18 Å, which means it is a weak interaction.

The C⋯H/H⋯C (17.7%, Fig. 6c) and Cl⋯H/H⋯Cl (Fig. 6e) contacts are seen as pairs of spikes at d_e + d_i = 2.9 and 2.9 Å, respectively.

The plot of O⋯H/H⋯O contacts between H atoms located inside the Hirshfeld surface and oxygen from outside and vice versa is shown in Fig. 6(d). These contacts account for 11.5% and are characterized by two symmetrical peaks with d_e + d_i = 2.5 Å; this reveals the presence of strong O⋯H contacts.

The C⋯C contacts (Fig. 6f) give a contribution of 10.5%, while the C⋯Cl, C⋯Se, Se⋯H/H⋯Se and Cl⋯Cl contacts in the structure give weak contributions of 4.3, 3.5, 2.8 and 2.4%, respectively, to the Hirshfeld surface.

5. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.40, last update May 2019; Groom et al., 2016 ) for 4,4′-substituted bis(phenyl) selenides yielded six relevant hits. These are bis(2-chloroethan-1-one-phenyl) selenide (CSD refcode HUYRUC; Bouraoui et al., 2015), bis(4-nitrophenyl) selenide (IDIOG; Zuo, 2013), bis(4-methoxyphenyl) selenide (LAFNAK; Verma et al., 2016 ), bis(4-acetylphenyl) selenide (UPAGAU; Bouraoui et al., 2011), bis(phenyl) selenide itself (YEWYUX; Bhandary et al., 2018 ) and bis(p-tolyl) selenide (TOLYSE; Blackmore & Abrahams, 1955 ). In IDIOG, the Se atom lies on a twofold rotation axis, and only YEWYUX and TOLYSE crystallize in chiral space groups, i.e. P2₁ and P2₁2₁2₁, respectively.

In the title compound (Fig. 1), the C—Se—C angle is 99.0 (2)°, similar to the value observed in five of the compounds mentioned above, viz. 100.03 (15), 99.47 (10), 102.25 (19), 99.59 (14) and 98.31 (16)° for HUYRUQ, IDITOG, LAFNAK, UPAGAU and YEWYUX, respectively. In the sixth compound, TOLYSE, the dihedral angle is 105.65 (19)°. The two inner benzene rings, A and C, in the title compound are inclined to each other by 79.1 (3)°. This value is quite different to that observed in the five compounds mentioned above, i.e. 69.92 (17), 63.76 (10), 69.6 (2), 87.08 (15), 68.46 (18) and ca 56.99° for HUYRUQ, IDITOG, LAFNAK, UPAGAU, YEWYUX and TOLYSE, respectively.

6. Synthesis and crystallization

The title compound was prepared according to a method proposed by Mechehoud et al. (2010 ). 2-Chloro-1-(4-chlorophenyl)ethan-1-one (ClC₈H₆COCl; 36.5 mmol) and anhydrous aluminium chloride (5 g, 37.5 mmol, 3 equiv.) were taken up in dry methylene chloride (100 ml). The reaction mixture was cooled to 273–278 K, protected from atmospheric moisture and stirred continuously for 15 min. A solution of diphenyl selenide (3 g, 1.87 mmol) in CH₂Cl₂ was added dropwise over a period of 5 min. The reaction mixture was allowed to reach room temperature gradually and then stirred at this temperature overnight. The solution was then washed with ice water–HCl (80 ml) and extracted with CH₂Cl₂. The organic layer was separated and dried (Na₂SO₄). Removal of the solvent under reduced pressure afforded the crude product, which was recrystallized from petroleum ether to yield 4.2 g of the title compound. Yellow single crystals suitable for X-ray diffraction analysis were obtained by recrystallization from CH₂Cl₂.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The H atoms could all be located in a difference Fourier map. During refinement, they were included in calculated positions and refined as riding on the parent C atom, with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C).

Table 3
Experimental details

Crystal data
Chemical formula	C₃₀H₂₀Cl₂O₂Se
M_r	562.32
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	4.9468 (3), 5.8712 (6), 21.3530 (18)
α, β, γ (°)	85.019 (8), 84.094 (6), 86.465 (7)
V (Å³)	613.68 (9)
Z	1
Radiation type	Mo Kα
μ (mm⁻¹)	1.77
Crystal size (mm)	0.03 × 0.02 × 0.01

Data collection
Diffractometer	Agilent Technologies Xcalibur Eos
No. of measured, independent and observed [I > 2σ(I)] reflections	5341, 3672, 2465
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.074, 0.81
No. of reflections	3672
No. of parameters	317
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.32
Absolute structure	Refined as an inversion twin
Absolute structure parameter	0.002 (11)
Computer programs: CrysAlis PRO (Agilent, 2013 ), SHELXS97 (Sheldrick, 2008 ), Mercury (Macrae et al., 2008), SHELXL2018 (Sheldrick, 2015 ), PLATON (Spek, 2009) and publCIF (Westrip, 2010 ).

Supporting information

CCDC references: 1959404; 1959404

Crystal structure: contains datablocks Global, I. DOI: https://doi.org/10.1107/S2056989019014038/su5517sup1.cif

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Agilent, 2013); cell refinement: CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(2E,2'E)-1,1'-[Selenobis(4,1-phenylene)]bis[3-(4-chlorophenyl)prop-2-en-1-one] top

Crystal data top

C₃₀H₂₀Cl₂O₂Se	Z = 1
M_r = 562.32	F(000) = 284
Triclinic, P1	D_x = 1.522 Mg m⁻³
a = 4.9468 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 5.8712 (6) Å	Cell parameters from 1538 reflections
c = 21.3530 (18) Å	θ = 3.9–28.9°
α = 85.019 (8)°	µ = 1.77 mm⁻¹
β = 84.094 (6)°	T = 293 K
γ = 86.465 (7)°	Prism, yellow
V = 613.68 (9) Å³	0.03 × 0.02 × 0.01 mm

Data collection top

Agilent Technologies Xcalibur Eos diffractometer	R_int = 0.030
Graphite monochromator	θ_max = 28.0°, θ_min = 2.9°
ω scans	h = −6→6
5341 measured reflections	k = −7→5
3672 independent reflections	l = −28→28
2465 reflections with I > 2σ(I)

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.074	w = 1/[σ²(F_o²) + (0.0181P)²] where P = (F_o² + 2F_c²)/3
S = 0.81	(Δ/σ)_max < 0.001
3672 reflections	Δρ_max = 0.41 e Å⁻³
317 parameters	Δρ_min = −0.32 e Å⁻³
3 restraints	Absolute structure: Refined as an inversion twin
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.002 (11)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq
Se1	0.41094 (7)	0.32993 (9)	0.51703 (4)	0.0688 (2)
Cl1	2.5172 (3)	0.7697 (3)	0.08312 (8)	0.0590 (4)
Cl2	2.0618 (3)	−0.0037 (3)	0.97993 (8)	0.0649 (5)
O1	1.4087 (9)	−0.1409 (9)	0.3126 (3)	0.0780 (15)
O2	0.9496 (10)	0.8409 (8)	0.7498 (2)	0.0823 (16)
C1	0.7186 (10)	0.2486 (11)	0.4597 (3)	0.0479 (15)
C2	0.8352 (11)	0.0295 (12)	0.4605 (3)	0.0615 (18)
H1	0.768523	−0.081384	0.490939	0.074*
C3	1.0483 (12)	−0.0293 (12)	0.4171 (3)	0.0593 (17)
H2	1.122475	−0.178850	0.418221	0.071*
C4	1.1520 (10)	0.1346 (11)	0.3718 (3)	0.0444 (14)
C5	1.0451 (11)	0.3551 (11)	0.3723 (3)	0.0503 (16)
H3	1.120388	0.468932	0.343979	0.060*
C6	0.8227 (12)	0.4092 (12)	0.4153 (3)	0.0553 (18)
H4	0.744240	0.557370	0.413526	0.066*
C7	1.3680 (11)	0.0604 (11)	0.3220 (3)	0.0507 (15)
C8	1.5292 (10)	0.2372 (11)	0.2840 (3)	0.0461 (15)
H5	1.522998	0.383771	0.297588	0.055*
C9	1.6809 (10)	0.1939 (11)	0.2315 (3)	0.0457 (15)
H6	1.666213	0.051207	0.216721	0.055*
C10	1.8698 (9)	0.3462 (10)	0.1941 (3)	0.0439 (14)
C11	2.0024 (10)	0.2799 (11)	0.1368 (3)	0.0499 (15)
H7	1.958306	0.143756	0.122056	0.060*
C12	2.1960 (11)	0.4092 (11)	0.1015 (3)	0.0534 (16)
H8	2.277520	0.364813	0.062900	0.064*
C13	2.2653 (10)	0.6084 (11)	0.1255 (3)	0.0464 (15)
C14	2.1353 (11)	0.6771 (12)	0.1810 (3)	0.0479 (15)
H9	2.180794	0.813002	0.195644	0.057*
C15	1.9411 (10)	0.5512 (11)	0.2153 (3)	0.0484 (15)
H10	1.855730	0.601551	0.252860	0.058*
C16	0.5992 (10)	0.4225 (11)	0.5837 (3)	0.0498 (16)
C17	0.7975 (12)	0.2824 (11)	0.6111 (3)	0.0577 (18)
H11	0.848615	0.141757	0.595285	0.069*
C18	0.9211 (12)	0.3470 (11)	0.6615 (3)	0.0542 (16)
H12	1.051962	0.248547	0.679406	0.065*
C19	0.8519 (11)	0.5582 (11)	0.6859 (3)	0.0457 (14)
C20	0.6508 (12)	0.6967 (12)	0.6588 (3)	0.0580 (17)
H13	0.596947	0.836179	0.675061	0.070*
C21	0.5295 (10)	0.6326 (11)	0.6087 (3)	0.0509 (15)
H14	0.398311	0.731000	0.590920	0.061*
C22	0.9847 (12)	0.6393 (11)	0.7381 (3)	0.0540 (16)
C23	1.1622 (12)	0.4833 (11)	0.7744 (3)	0.0510 (16)
H15	1.186238	0.331934	0.764354	0.061*
C24	1.2909 (10)	0.5463 (11)	0.8210 (3)	0.0499 (15)
H16	1.258745	0.697969	0.830360	0.060*
C25	1.4776 (10)	0.4073 (10)	0.8597 (3)	0.0453 (14)
C26	1.5525 (11)	0.4873 (11)	0.9142 (3)	0.0574 (17)
H17	1.481261	0.629389	0.925872	0.069*
C27	1.7295 (11)	0.3629 (12)	0.9516 (3)	0.0553 (16)
H18	1.775600	0.419691	0.988224	0.066*
C28	1.8357 (10)	0.1557 (11)	0.9342 (3)	0.0505 (16)
C29	1.7647 (11)	0.0694 (11)	0.8801 (3)	0.0529 (17)
H19	1.836285	−0.073216	0.868869	0.063*
C30	1.5893 (10)	0.1942 (10)	0.8431 (3)	0.0522 (16)
H20	1.544135	0.136366	0.806609	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.0439 (3)	0.1060 (6)	0.0592 (4)	−0.0158 (3)	0.0067 (3)	−0.0279 (4)
Cl1	0.0504 (8)	0.0624 (11)	0.0618 (11)	−0.0106 (7)	0.0025 (7)	0.0047 (9)
Cl2	0.0606 (9)	0.0696 (12)	0.0622 (11)	0.0083 (9)	−0.0051 (8)	−0.0008 (10)
O1	0.101 (4)	0.052 (3)	0.075 (4)	−0.015 (3)	0.031 (3)	−0.013 (3)
O2	0.130 (4)	0.054 (3)	0.068 (3)	0.025 (3)	−0.035 (3)	−0.024 (3)
C1	0.038 (3)	0.067 (5)	0.042 (4)	−0.014 (3)	−0.004 (2)	−0.013 (3)
C2	0.061 (4)	0.075 (5)	0.047 (4)	−0.024 (4)	0.017 (3)	−0.010 (4)
C3	0.066 (4)	0.053 (4)	0.057 (5)	−0.020 (3)	0.011 (3)	−0.004 (4)
C4	0.040 (3)	0.060 (4)	0.036 (3)	−0.012 (3)	−0.003 (2)	−0.014 (3)
C5	0.057 (4)	0.059 (4)	0.033 (4)	−0.009 (3)	0.004 (3)	−0.002 (3)
C6	0.051 (4)	0.061 (5)	0.057 (5)	−0.010 (3)	−0.004 (3)	−0.019 (4)
C7	0.056 (3)	0.054 (4)	0.043 (4)	−0.016 (3)	0.007 (3)	−0.013 (3)
C8	0.046 (3)	0.053 (4)	0.039 (4)	−0.007 (3)	0.006 (3)	−0.016 (3)
C9	0.041 (3)	0.050 (4)	0.046 (4)	0.002 (3)	−0.004 (3)	−0.002 (3)
C10	0.039 (3)	0.048 (4)	0.045 (3)	0.003 (3)	0.000 (2)	−0.010 (3)
C11	0.060 (4)	0.046 (4)	0.045 (4)	−0.002 (3)	0.002 (3)	−0.017 (3)
C12	0.056 (4)	0.063 (5)	0.040 (4)	−0.012 (3)	0.012 (3)	−0.011 (3)
C13	0.037 (3)	0.056 (4)	0.042 (3)	0.007 (3)	−0.003 (2)	0.012 (3)
C14	0.053 (3)	0.050 (4)	0.040 (4)	−0.003 (3)	−0.001 (3)	−0.004 (3)
C15	0.048 (3)	0.059 (4)	0.038 (3)	0.002 (3)	0.002 (3)	−0.013 (3)
C16	0.036 (3)	0.062 (4)	0.050 (4)	−0.019 (3)	0.013 (3)	−0.010 (3)
C17	0.061 (4)	0.047 (4)	0.065 (5)	−0.003 (3)	0.007 (3)	−0.016 (4)
C18	0.064 (4)	0.053 (4)	0.045 (4)	−0.008 (3)	0.006 (3)	−0.012 (3)
C19	0.049 (3)	0.050 (4)	0.036 (3)	−0.003 (3)	0.006 (3)	−0.005 (3)
C20	0.064 (4)	0.059 (4)	0.049 (4)	0.002 (3)	0.009 (3)	−0.014 (3)
C21	0.045 (3)	0.060 (4)	0.047 (4)	0.000 (3)	0.003 (3)	−0.009 (3)
C22	0.066 (4)	0.054 (4)	0.037 (3)	0.016 (3)	0.004 (3)	−0.003 (3)
C23	0.075 (4)	0.038 (4)	0.039 (4)	−0.003 (3)	0.004 (3)	−0.002 (3)
C24	0.056 (3)	0.049 (4)	0.042 (3)	0.002 (3)	0.006 (3)	−0.004 (3)
C25	0.045 (3)	0.046 (4)	0.044 (4)	−0.005 (3)	0.006 (3)	−0.009 (3)
C26	0.059 (4)	0.052 (4)	0.061 (5)	0.000 (3)	0.006 (3)	−0.015 (4)
C27	0.050 (3)	0.069 (5)	0.047 (4)	0.008 (3)	−0.002 (3)	−0.019 (3)
C28	0.040 (3)	0.059 (4)	0.049 (4)	−0.002 (3)	0.006 (3)	0.001 (3)
C29	0.060 (4)	0.042 (4)	0.057 (4)	0.016 (3)	−0.012 (3)	−0.012 (3)
C30	0.056 (3)	0.052 (4)	0.050 (4)	−0.004 (3)	−0.002 (3)	−0.020 (3)

Geometric parameters (Å, º) top

Se1—C1	1.916 (5)	C14—C15	1.362 (8)
Se1—C16	1.913 (6)	C14—H9	0.9300
Cl1—C13	1.741 (6)	C15—H10	0.9300
Cl2—C28	1.737 (6)	C16—C17	1.385 (8)
O1—C7	1.217 (7)	C16—C21	1.396 (8)
O2—C22	1.229 (7)	C17—C18	1.383 (9)
C1—C2	1.376 (8)	C17—H11	0.9300
C1—C6	1.364 (8)	C18—C19	1.396 (8)
C2—C3	1.377 (8)	C18—H12	0.9300
C2—H1	0.9300	C19—C20	1.387 (7)
C3—C4	1.386 (8)	C19—C22	1.477 (8)
C3—H2	0.9300	C20—C21	1.371 (8)
C4—C5	1.368 (8)	C20—H13	0.9300
C4—C7	1.500 (7)	C21—H14	0.9300
C5—C6	1.398 (8)	C22—C23	1.459 (7)
C5—H3	0.9300	C23—C24	1.325 (8)
C6—H4	0.9300	C23—H15	0.9300
C7—C8	1.482 (8)	C24—C25	1.466 (7)
C8—C9	1.317 (8)	C24—H16	0.9300
C8—H5	0.9300	C25—C26	1.383 (8)
C9—C10	1.462 (8)	C25—C30	1.395 (7)
C9—H6	0.9300	C26—C27	1.380 (8)
C10—C11	1.401 (7)	C26—H17	0.9300
C10—C15	1.400 (8)	C27—C28	1.361 (8)
C11—C12	1.380 (7)	C27—H18	0.9300
C11—H7	0.9300	C28—C29	1.387 (8)
C12—C13	1.392 (8)	C29—C30	1.369 (7)
C12—H8	0.9300	C29—H19	0.9300
C13—C14	1.369 (8)	C30—H20	0.9300

C1—Se1—C16	99.0 (2)	C17—C16—C21	117.4 (6)
C2—C1—C6	118.2 (5)	C17—C16—Se1	122.2 (5)
C2—C1—Se1	122.1 (5)	C21—C16—Se1	120.3 (5)
C6—C1—Se1	119.7 (5)	C18—C17—C16	121.4 (6)
C1—C2—C3	121.5 (6)	C18—C17—H11	119.3
C1—C2—H1	119.2	C16—C17—H11	119.3
C3—C2—H1	119.2	C17—C18—C19	120.8 (6)
C2—C3—C4	120.0 (6)	C17—C18—H12	119.6
C2—C3—H2	120.0	C19—C18—H12	119.6
C4—C3—H2	120.0	C20—C19—C18	117.6 (6)
C5—C4—C3	119.0 (5)	C20—C19—C22	119.4 (6)
C5—C4—C7	122.4 (5)	C18—C19—C22	123.0 (6)
C3—C4—C7	118.5 (6)	C21—C20—C19	121.5 (6)
C4—C5—C6	120.0 (6)	C21—C20—H13	119.3
C4—C5—H3	120.0	C19—C20—H13	119.3
C6—C5—H3	120.0	C20—C21—C16	121.3 (6)
C1—C6—C5	121.2 (6)	C20—C21—H14	119.4
C1—C6—H4	119.4	C16—C21—H14	119.4
C5—C6—H4	119.4	O2—C22—C19	119.4 (6)
O1—C7—C8	120.5 (6)	O2—C22—C23	120.2 (6)
O1—C7—C4	120.7 (6)	C19—C22—C23	120.4 (6)
C8—C7—C4	118.7 (6)	C24—C23—C22	123.3 (6)
C9—C8—C7	122.3 (6)	C24—C23—H15	118.3
C9—C8—H5	118.9	C22—C23—H15	118.3
C7—C8—H5	118.9	C23—C24—C25	128.2 (6)
C8—C9—C10	127.0 (6)	C23—C24—H16	115.9
C8—C9—H6	116.5	C25—C24—H16	115.9
C10—C9—H6	116.5	C26—C25—C30	117.6 (5)
C11—C10—C15	117.6 (6)	C26—C25—C24	120.2 (6)
C11—C10—C9	119.8 (6)	C30—C25—C24	122.2 (6)
C15—C10—C9	122.5 (6)	C27—C26—C25	122.1 (6)
C12—C11—C10	122.4 (6)	C27—C26—H17	118.9
C12—C11—H7	118.8	C25—C26—H17	118.9
C10—C11—H7	118.8	C28—C27—C26	119.0 (6)
C13—C12—C11	117.8 (6)	C28—C27—H18	120.5
C13—C12—H8	121.1	C26—C27—H18	120.5
C11—C12—H8	121.1	C27—C28—C29	120.6 (5)
C12—C13—C14	120.5 (6)	C27—C28—Cl2	120.1 (5)
C12—C13—Cl1	118.7 (5)	C29—C28—Cl2	119.3 (5)
C14—C13—Cl1	120.8 (6)	C30—C29—C28	120.0 (6)
C15—C14—C13	121.6 (7)	C30—C29—H19	120.0
C15—C14—H9	119.2	C28—C29—H19	120.0
C13—C14—H9	119.2	C29—C30—C25	120.7 (6)
C14—C15—C10	120.1 (6)	C29—C30—H20	119.7
C14—C15—H10	120.0	C25—C30—H20	119.7
C10—C15—H10	120.0

C6—C1—C2—C3	−1.1 (9)	C21—C16—C17—C18	0.4 (9)
Se1—C1—C2—C3	176.9 (5)	Se1—C16—C17—C18	−176.5 (5)
C1—C2—C3—C4	0.7 (10)	C16—C17—C18—C19	−0.9 (10)
C2—C3—C4—C5	2.0 (9)	C17—C18—C19—C20	1.6 (9)
C2—C3—C4—C7	−174.9 (6)	C17—C18—C19—C22	−177.7 (6)
C3—C4—C5—C6	−4.2 (9)	C18—C19—C20—C21	−2.0 (9)
C7—C4—C5—C6	172.5 (6)	C22—C19—C20—C21	177.4 (5)
C2—C1—C6—C5	−1.3 (9)	C19—C20—C21—C16	1.5 (9)
Se1—C1—C6—C5	−179.3 (5)	C17—C16—C21—C20	−0.7 (8)
C4—C5—C6—C1	4.0 (10)	Se1—C16—C21—C20	176.2 (4)
C5—C4—C7—O1	−160.6 (6)	C20—C19—C22—O2	−12.2 (9)
C3—C4—C7—O1	16.1 (9)	C18—C19—C22—O2	167.1 (6)
C5—C4—C7—C8	18.7 (8)	C20—C19—C22—C23	169.6 (6)
C3—C4—C7—C8	−164.5 (5)	C18—C19—C22—C23	−11.1 (9)
O1—C7—C8—C9	13.7 (10)	O2—C22—C23—C24	0.5 (10)
C4—C7—C8—C9	−165.7 (5)	C19—C22—C23—C24	178.8 (5)
C7—C8—C9—C10	−172.9 (5)	C22—C23—C24—C25	−178.6 (5)
C8—C9—C10—C11	−175.5 (6)	C23—C24—C25—C26	−167.4 (6)
C8—C9—C10—C15	9.4 (8)	C23—C24—C25—C30	13.7 (9)
C15—C10—C11—C12	−0.3 (8)	C30—C25—C26—C27	−0.5 (9)
C9—C10—C11—C12	−175.6 (5)	C24—C25—C26—C27	−179.4 (5)
C10—C11—C12—C13	2.1 (8)	C25—C26—C27—C28	0.6 (10)
C11—C12—C13—C14	−2.9 (8)	C26—C27—C28—C29	−0.8 (9)
C11—C12—C13—Cl1	177.9 (4)	C26—C27—C28—Cl2	179.3 (5)
C12—C13—C14—C15	1.9 (9)	C27—C28—C29—C30	0.9 (9)
Cl1—C13—C14—C15	−178.9 (4)	Cl2—C28—C29—C30	−179.2 (5)
C13—C14—C15—C10	0.0 (8)	C28—C29—C30—C25	−0.8 (9)
C11—C10—C15—C14	−0.8 (8)	C26—C25—C30—C29	0.6 (9)
C9—C10—C15—C14	174.4 (5)	C24—C25—C30—C29	179.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C29—H19···O2ⁱ	0.93	2.63	3.218 (8)	122

Symmetry code: (i) x+1, y−1, z.

Relative percentage contributions of the close contacts to the Hirshfeld surface of the title compound. top

Contact	Percentage contribution
H···H	36.0
C···H/H···C	17.7
O···H/H···O	11.5
Cl···H/H···Cl	11.0
C···C	10.5
C···Cl	4.3
C···Se	3.5
Se···H/H···Se	2.8
Cl···Cl	2.4
C···O	0.3

Short contacts (Å) in the crystal of the title compound. top

Atom 1	Atom 2	Length (Å)	Length-VdW (Å)
H3	H10ⁱ	2.498	0.098
O2	H19ⁱⁱ	2.632	-0.088
H12	O2ⁱⁱⁱ	2.759	0.039
O1	H3ⁱⁱⁱ	2.770	0.050
O2	H20ⁱⁱ	2.818	0.098
H2	C6ⁱⁱⁱ	2.922	0.022
C3	H4ⁱⁱ	2.943	0.043
H3	C15ⁱ	2.964	0.064
O2	C29ⁱⁱ	3.217	-0.003
O2	C30ⁱⁱ	3.314	0.094
C5	C8ⁱ	3.461	0.061
Se1	C17ⁱ	3.475	-0.125
C20	C23ⁱ	3.480	0.080
Cl2	Cl1^iv	3.549	0.049

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

Acknowledgements

This work was supported by the Laboratoire de Cristallographie, Departement de Physique, Universite Constantine 1, Algeria. We also thank Mr F. Saidi, Engineer at the Laboratory of Crystallography, University Constantine 1, for assistance in collecting data on the Xcalibur X-ray diffractometer.

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