Crystal structure, Hirshfeld surface analysis and inter­action energy and DFT studies of 3-{(2Z)-2-[(2,4-di­chloro­phen­yl)methyl­idene]-3-oxo-3,4-di­hydro-2H-1,4-benzo­thia­zin-4-yl}propane­nitrile

Sebbar, N.K.; Hni, B.; Hökelek, T.; Jaouhar, A.; Labd Taha, M.; Mague, J.T.; Essassi, E.M.

doi:10.1107/S2056989019005966

research communications

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ISSN: 2056-9890

Volume 75| Part 6| June 2019| Pages 721-727

https://doi.org/10.1107/S2056989019005966

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Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 3-{(2Z)-2-[(2,4-dichlorophenyl)methylidene]-3-oxo-3,4-dihydro-2H-1,4-benzothiazin-4-yl}propanenitrile

Nada Kheira Sebbar,^a,^b ^* Brahim Hni,^b Tuncer Hökelek,^c Abdelhakim Jaouhar,^a Mohamed Labd Taha,^a Joel T. Mague ^d and El Mokhtar Essassi ^b

^aLaboratoire de Chimie Appliquée et Environnement, Equipe de Chimie Bioorganique Appliquée, Faculté des Sciences, Université Ibn Zohr, Agadir, Morocco, ^bLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de Compétence Pharmacochimie, Av. Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, ^cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey, and ^dDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: nadouchsebbarkheira@gmail.com

Edited by A. J. Lough, University of Toronto, Canada (Received 15 April 2019; accepted 29 April 2019; online 3 May 2019)

The title compound, C₁₈H₁₂Cl₂N₂OS, consists of a dihydrobenzothiazine unit linked by a –CH group to a 2,4-dichlorophenyl substituent, and to a propanenitrile unit is folded along the S⋯N axis and adopts a flattened-boat conformation. The propanenitrile moiety is nearly perpendicular to the mean plane of the dihydrobenzothiazine unit. In the crystal, C—H_Bnz⋯N_Prpnit and C—H_Prpnit⋯O_Thz (Bnz = benzene, Prpnit = propanenitrile and Thz = thiazine) hydrogen bonds link the molecules into inversion dimers, enclosing R₂²(16) and R₂²(12) ring motifs, which are linked into stepped ribbons extending along [110]. The ribbons are linked in pairs by complementary C=O⋯Cl interactions. π–π contacts between the benzene and phenyl rings, [centroid–centroid distance = 3.974 (1) Å] may further stabilize the structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (23.4%), H⋯Cl/Cl⋯H (19.5%), H⋯C/C⋯H (13.5%), H⋯N/N⋯H (13.3%), C⋯C (10.4%) and H⋯O/O⋯H (5.1%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry calculations indicate that the two independent C—H_Bnz⋯N_Prpnit and C—H_Prpnit⋯O_Thz hydrogen bonds in the crystal impart about the same energy (ca 43 kJ mol⁻¹). Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

Keywords: crystal structure; hydrogen bond; oxygen⋯halogen interaction; nitrile; dihydrobenzothiazine; DFT; Hirshfeld surface.

CCDC reference: 1913051

1. Chemical context

1,4-Benzothiazine derivatives constitute an important class of heterocyclic systems. These molecules exhibit a wide range of biological applications indicating that the 1,4-benzothiazine moiety is a potentially useful template in medicinal chemistry research and has therapeutic applications as anti-inflammatory (Trapani et al., 1985 ; Gowda et al., 2011 ), antipyretic (Warren & Knaus, 1987 ), anti-microbial (Armenise et al., 2012 ; Rathore & Kumar, 2006 ; Sabatini et al., 2008 ), anti-viral (Malagu et al., 1998 ), anti-cancer (Gupta et al., 1985 ; Gupta & Gupta, 1991 ) and anti-oxidant (Zia-ur-Rehman et al., 2009 ) agents. 1,4-Benzothiazine derivatives have also been reported as precursors for the syntheses of new compounds (Sebbar et al., 2015a ; Vidal et al., 2006 ) possessing anti-diabetic (Tawada et al., 1990 ) and anti-corrosion activities (Ellouz et al., 2016a ,b ; Sebbar et al., 2016a ). They also possess biological properties (Hni et al., 2019a ; Saber et al., 2018 ; Ellouz et al., 2017a ,b , 2018 ; Sebbar et al., 2017 ). As a continuation of our research work on the development of N-substituted 1,4-benzothiazine derivatives and the evaluation of their potential pharmacological activities, we report herein the synthesis and the molecular and crystal structures of the title compound along with the Hirshfeld surface analysis and the intermolecular interaction energies and the density functional theory (DFT) computational calculations carried out at the B3LYP/6–31 G(d,p) and B3LYP/6–311 G(d,p) levels, respectively.

2. Structural commentary

The title compound, (I), consists of a dihydrobenzothiazine unit linked by a –CH group to a 2,4-dichlorophenyl substituent and to a propanenitrile moiety (Fig. 1). The dihydrobenzothiazine unit is folded along the S⋯N axis by 13.50 (9)°. The benzene ring, A (C1–C6), is oriented at a dihedral angle of 1.89 (6)° with respect to the phenyl ring, C (C10–C15). A puckering analysis of the heterocyclic ring B (S1/N1/C1/C6–C8) of the dihydrobenzothiazine unit gave the parameters Q_T = 0.1983 (15) Å, q₂ = 0.1957 (17) Å, q₃ = 0.0323 (19) Å, φ = 354.6 (6)° and θ = 80.8 (5)°, indicating it adopts a flattened-boat conformation. The propanenitrile moiety is essentially perpendicular to the dihydrobenzothiazine unit, as indicated by the C7—N1—C16—C17 torsion angle of 88.6 (2)°. In heterocyclic ring B, the C1—S1—C8 [103.69 (9)°], S1—C8—C7 [121.12 (14)°], C8—C7—N1 [120.59 (17)°], C7—N1—C6 [126.27 (16)°], C6—C1—S1 [123.84 (15)°] and N1—C6—C1 [121.46 (17)°] bond angles are enlarged when compared with the corresponding values in the closely related compounds, (2Z)-2-(4-chlorobenzylidene)-4-[2-(2-oxooxazoliden-3-yl) ethyl]-3,4-dihydro-2H-1,4-benzothiazin-3-one, (II), (Ellouz et al., 2017a) and (2Z)-2-[(4-fluorobenzylidene]-4-(prop-2-yn-1-yl)-3,4 -dihydro-2H-1,4-benzothiazin-3-one, (III), (Hni et al., 2019a), and are nearly the same as the corresponding values in (2Z)-4-[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]-2(phenylmethylidene)-3,4-dihydro-2H-1,4-benzothiazin-3-one, (IV), (Sebbar et al., 2016b ) and (2Z)-2-[(2,4-dichlorophenyl)methylidene]-4-[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]3,4-dihydro-2H-1,4-benzothiazin-3-one, (V), (Hni et al., 2019b ), where the heterocyclic portions of the dihydrobenzothiazine units are planar in (IV) and non-planar in (II), (III) and (V).

Figure 1
The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

3. Supramolecular features

In the crystal, inversion dimers are formed by C—H_Bnz⋯N_Prpnit (Bnz = benzene and Prpnit = propanenitrile) hydrogen bonds (Table 1 and Fig. 2), enclosing R₂²(16) ring motifs, and these units are linked into stepped ribbons extending along [110] by inversion-related C—H_Prpnit⋯O_Thz (Thz = thiazine) hydrogen bonds (Table 1 and Fig. 2), enclosing R₂²(12) ring motifs. The ribbons are arranged in pairs with inversion-related Cl2⋯O1 contacts of 3.027 (2) Å and C15=O1⋯Cl2 angles of 170.41 (7)° (Fig. 3). The contact is noticeably less than the sum of the van der Waals radii (3.27 Å), and the contact and angle compare well with corresponding parameters found in the structure of 2,5-dichloro-1,4-benzoquinone and attributed to attractive O⋯Cl interactions (Lommerse et al., 1996). The π–π contacts between the benzene (C1–C6, centroid Cg1) and 2,4-dichlorophenyl rings (C10–C15, centroid Cg3) [Cg1⋯Cg3(x − 1, y − 1, z) = 3.974 (1) Å] may further stabilize the structure.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N2^viii	0.95	2.43	3.282 (3)	149
C17—H17A⋯O1^vii	0.99	2.45	3.337 (3)	149
Symmetry codes: (vii) -x+1, -y+1, -z+1; (viii) -x, -y, -z+1.

Figure 2
A partial packing diagram viewed along the c-axis direction with the C—H⋯O and C—H⋯N hydrogen bonds shown, respectively, as black and blue dashed lines.

Figure 3
A partial packing diagram viewed along the a-axis direction with hydrogen bonds depicted as in Fig. 2

, and C=O⋯Cl interactions as green dashed lines.

4. Hirshfeld surface analysis

In order to visualize the intermolecular interactions in the crystal of the title compound, a Hirshfeld surface (HS) analysis (Hirshfeld, 1977 ; Spackman & Jayatilaka, 2009 ) was carried out by using CrystalExplorer17.5 (Turner et al., 2017 . In the HS plotted over d_norm (Fig. 4), the white surface indicates contacts with distances equal to the sum of van der Waals radii, and the red and blue colours indicate distances shorter (in close contact) or longer (distinct contact) than the van der Waals radii, respectively (Venkatesan et al., 2016 ). The bright-red spots indicate their roles as the respective donors and/or acceptors; they also appear as blue and red regions corresponding to positive and negative potentials on the HS mapped over electrostatic potential (Spackman et al., 2008 ; Jayatilaka et al., 2005 ) shown in Fig. 5. The blue regions indicate positive electrostatic potential (hydrogen-bond donors), while the red regions indicate negative electrostatic potential (hydrogen-bond acceptors). The shape-index of the HS is a tool to visualize the π–π stacking by the presence of adjacent red and blue triangles; if there are no adjacent red and/or blue triangles, then there are no π–π interactions. Fig. 6 clearly suggest that there are π–π interactions in (I).

Figure 4
View of the three-dimensional Hirshfeld surface of the title compound plotted over d_norm in the range −0.2386 to 1.2893 a.u.

Figure 5
View of the three-dimensional Hirshfeld surface of the title compound plotted over electrostatic potential energy in the range −0.0500 to 0.0500 a.u. using the STO-3 G basis set at the Hartree–Fock level of theory. Hydrogen-bond donors and acceptors are shown as blue and red regions around the atoms corresponding to positive and negative potentials, respectively.

Figure 6
Hirshfeld surface of the title compound plotted over shape-index.

The overall two-dimensional fingerprint plot, Fig. 7a, and those delineated into H⋯H, H⋯Cl/Cl⋯H, H⋯C/C⋯H, H⋯N/N⋯H, C⋯C, H⋯O/O⋯H, C⋯Cl/Cl⋯C, H⋯S/S⋯H, C⋯S/S⋯C, O⋯Cl/Cl⋯O and C⋯N/N⋯C contacts (McKinnon et al., 2007 ) are illustrated in Fig. 7b–l, respectively, together with their relative contributions to the Hirshfeld surface. The most important interaction is H⋯H (Table 2), contributing 23.4% to the overall crystal packing, which is reflected in Fig. 7b as widely scattered points of high density due to the large hydrogen content of the molecule with the small split tips at d_e + d_i = 2.32 Å. The pair of wings in the fingerprint plot delineated into H⋯Cl/Cl⋯H contacts (19.5% contribution) have a nearly symmetrical distribution of points, Fig. 7c, with the thin edges at d_e + d_i = 2.82 Å. In the absence of C—H⋯π interactions, the wings in the fingerprint plot delineated into H⋯C/C⋯H contacts (13.5%) also have a nearly symmetrical distribution of points, Fig. 7d, with the thick edges at d_e + d_i ∼2.90 Å. The wings in the fingerprint plot delineated into H⋯N/N⋯H contacts (13.3%, Fig. 7e) have as pair of spikes with the tips at d_e + d_i = 2.30 Å. The C⋯C contacts (10.4%, Fig. 7f) have an arrow-shaped distribution of points with the tip at d_e = d_i ∼1.78 Å. The H⋯O/O⋯H (5.1%, Fig. 7g) and C⋯Cl/Cl⋯C (4.6%, Fig. 7h) contacts (Table 2) are viewed as pairs of thin spikes with the tips at d_e + d_i = 2.34 and 3.50 Å, respectively. Finally, the H⋯S/S ⋯ H (2.6%, Fig. 7i) and C⋯S/S⋯C (2.3%, Fig. 7j) contacts are seen as pairs of wide spikes with the tips at d_e + d_i ∼3.30 and 3.48 Å, respectively.

Table 2
Selected interatomic distances (Å)

Cl2⋯C18ⁱ	3.649 (2)	N2⋯H16A^ix	2.81
Cl2⋯C7ⁱⁱ	3.520 (2)	C2⋯C11^vi	3.569 (3)
Cl2⋯O1ⁱ	3.0269 (15)	C4⋯C12^x	3.577 (3)
Cl1⋯H2ⁱⁱⁱ	3.00	C4⋯C8^vi	3.490 (3)
Cl1⋯H4^iv	2.94	C5⋯C14^x	3.557 (3)
Cl2⋯H17Aⁱⁱ	3.06	C5⋯C17	3.352 (3)
Cl2⋯H9	2.51	C8⋯C4ⁱⁱ	3.490 (3)
Cl2⋯H16B^v	2.96	C9⋯C18^vii	3.497 (3)
S1⋯N1	3.1168 (17)	C11⋯C2ⁱⁱ	3.569 (3)
S1⋯C3ⁱⁱ	3.598 (2)	C12⋯C4^v	3.577 (3)
S1⋯C4ⁱⁱ	3.510 (2)	C14⋯C5^v	3.557 (3)
S1⋯C11	3.162 (2)	C17⋯C5	3.352 (3)
S1⋯C14^vi	3.578 (2)	C18⋯C9^vii	3.497 (3)
S1⋯H11	2.47	C5⋯H16B	2.53
O1⋯C17	3.210 (2)	C5⋯H17B	2.86
O1⋯Cl2ⁱ	3.0269 (15)	C8⋯H11	2.94
O1⋯C17^vii	3.336 (3)	C16⋯H5	2.48
O1⋯H17A	2.79	C17⋯H5	2.79
O1⋯H9	2.24	C18⋯H9^vii	2.98
O1⋯H16A	2.29	H2⋯H12^xi	2.49
O1⋯H17A^vii	2.45	H5⋯H16B	2.03
N2⋯C5^viii	3.282 (3)	H5⋯H17B	2.26
N2⋯H5^viii	2.43
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x+1, y, z; (iii) -x+2, -y+1, -z; (iv) x+2, y+1, z; (v) x+1, y+1, z; (vi) x-1, y, z; (vii) -x+1, -y+1, -z+1; (viii) -x, -y, -z+1; (ix) -x+1, -y, -z+1; (x) x-1, y-1, z; (xi) -x+1, -y+1, -z.

Figure 7
The full two-dimensional fingerprint plots for the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) H⋯Cl/Cl⋯H, (d) H⋯C/C⋯H, (e) H⋯N/N⋯H, (f) C⋯C, (g) H⋯O/O⋯H, (h) C⋯Cl/Cl⋯C, (i) H⋯S/S⋯H, (j) C⋯S/S⋯C, (k) O⋯Cl/Cl⋯O and (l) C⋯N/N⋯C interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface contacts.

The Hirshfeld surface representations with the function d_norm plotted onto the surface are shown for the H⋯H, H⋯Cl/Cl⋯H, H⋯C/C⋯H, H ⋯ N/N⋯H, C⋯C and H⋯O/O⋯H interactions in Fig. 8a–f, respectively.

Figure 8
The Hirshfeld surface representations with the function d_norm plotted onto the surface for (a) H⋯H, (b) H⋯Cl/Cl⋯H, (c) H⋯C/C⋯H, (d) H⋯N/N⋯H, (e) C⋯C and (f) H⋯O/O⋯H interactions.

The Hirshfeld surface analysis confirms the importance of H-atom contacts in establishing the packing. The large number of H⋯H, H⋯Cl/Cl⋯H, H ⋯ C/C⋯H and H⋯N/N⋯H interactions suggest that van der Waals interactions and hydrogen bonding play the major roles in the crystal packing (Hathwar et al., 2015 ).

5. Interaction energy calculations

The intermolecular interaction energies were calculated using the CE–B3LYP/6–31G(d,p) energy model available in CrystalExplorer17.5 (Turner et al., 2017), where a cluster of molecules is generated by applying crystallographic symmetry operations with respect to a selected central molecule within a default radius of 3.8 Å (Turner et al., 2014 ). The total intermolecular energy (E_tot) is the sum of electrostatic (E_ele), polarization (E_pol), dispersion (E_dis) and exchange-repulsion (E_rep) energies (Turner et al., 2015 ) with scale factors of 1.057, 0.740, 0.871 and 0.618, respectively (Mackenzie et al., 2017 ). Hydrogen-bonding interaction energies (in kJ mol⁻¹) were calculated to be −13.0 (E_ele), −1.8 (E_pol), −68.0 (E_dis), 48.3 (E_rep) and −44.4 (E_tot) for the C—H_Bnz⋯N_Prpnit hydrogen-bonding interaction and −37.3 (E_ele), −9.3 (E_pol), −19.0 (E_dis), 33.7 (E_rep) and −42.0 (E_tot) for C—H_Prpnit⋯O_Thz.

6. DFT calculations

The optimized structure of the title compound in the gas phase was generated theoretically via density functional theory (DFT) using standard B3LYP functional and 6–311 G(d,p) basis-set calculations (Becke, 1993 ) as implemented in GAUSSIAN 09 (Frisch et al., 2009 ). The theoretical and experimental results were in good agreement. The highest-occupied molecular orbital (HOMO), acting as an electron donor, and the lowest-unoccupied molecular orbital (LUMO), acting as an electron acceptor, are very important parameters for quantum chemistry. When the energy gap is small, the molecule is highly polarizable and has high chemical reactivity. The electron transition from the HOMO to the LUMO energy level is shown in Fig. 9. The HOMO and LUMO are localized in the plane extending from the whole 3-[(2Z)-2-[(2,4-dichlorophenyl)methylidene]-3-oxo-3,4-dihydro-2H-1,4-benzothiazin-4-yl]propanenitrile ring. The energy band gap [ΔE = E_LUMO − E_HOMO] of the molecule is about 6.1979 eV, and the frontier molecular orbital energies, E_HOMO and E_LUMO are −7.1543 and −0.9564 eV, respectively.

Figure 9
The energy band gap of the title compound.

7. Database survey

A search in the Cambridge Structural Database (Groom et al., 2016 ; updated to March 2019), for compounds containing the fragment II (R₁ = Ph, R₂ = C), gave 14 hits. With R₁ = Ph and R₂ = CH₂C≡CH IIa (Sebbar et al., 2014a ), CH₂COOH IIb (Sebbar et al., 2016c ), IIc (Sebbar et al., 2016b) and IIf (Sebbar et al., 2015b ), there are other examples with R₁ = 4-FC₆H₄ and R₂ = CH₂C≡CH IIa (Hni et al., 2019a), R₁ = 4-ClC₆H₄ and R₂ = CH₂Ph2 IId (Ellouz et al., 2016c ) and R₁ = 2-ClC₆H₄, R₂ = CH₂C≡CH IIa (Sebbar et al., 2017). In all these compounds, the configuration about the benzylidene C=CHC₆H₅ bond is Z, and in the majority of these, the heterocyclic ring is quite non-planar with the dihedral angle between the plane defined by the benzene ring plus the nitrogen and sulfur atoms and that defined by nitrogen and sulfur and the other two carbon atoms separating them ranging from ca 29° (IIa) to 36° (IIf). The other three (IIa, IIc) have the benzothiazine unit nearly planar with a corresponding dihedral angle of ca 3–4°

8. Synthesis and crystallization

3-Bromopropanenitrile (2.0 mmol) was added to a mixture of (Z)-2-(2,4-dichlorobenzylidene)-2H-1,4-benzothiazin-3(4H)-one (1.8 mmol), potassium carbonate (2.0 mmol) and tetra n-butyl ammonium bromide (0.15 mmol) in DMF (20 ml). Stirring was continued at room temperature for 12 h. The salts were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was separated by chromatography on a column of silica gel with ethyl acetate–hexane (1/9) as eluent. The solid product obtained was recrystallized from ethanol to afford colourless crystals (yield: 82%).

9. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. C-bound H atoms were positioned geometrically (C—H = 0.95 Å for aromatic and methine H atoms and 0.99 Å for methylene H atoms) and constrained to ride on their parent atoms, with U_iso(H) = 1.2U_eq(C).

Table 3
Experimental details

Crystal data
Chemical formula	C₁₈H₁₂Cl₂N₂OS
M_r	375.26
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	150
a, b, c (Å)	6.5687 (6), 7.9971 (7), 15.4939 (13)
α, β, γ (°)	98.105 (4), 94.316 (4), 95.002 (4)
V (Å³)	799.54 (12)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	4.93
Crystal size (mm)	0.20 × 0.14 × 0.10

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Numerical (SADABS; Krause et al., 2015 )
T_min, T_max	0.47, 0.65
No. of measured, independent and observed [I > 2σ(I)] reflections	6131, 2978, 2744
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.095, 1.06
No. of reflections	2978
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.35
Computer programs: SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Supporting information

CCDC reference: 1913051

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989019005966/lh5901sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019005966/lh5901Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989019005966/lh5901Isup3.cdx

checkCIF report

Computing details top

Cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

3-{(2Z)-2-[(2,4-Dichlorophenyl)methylidene]-3-oxo-3,4-dihydro-2H-1,4-benzothiazin-4-yl}propanenitrile top

Crystal data top

C₁₈H₁₂Cl₂N₂OS	Z = 2
M_r = 375.26	F(000) = 384
Triclinic, P1	D_x = 1.559 Mg m⁻³
a = 6.5687 (6) Å	Cu Kα radiation, λ = 1.54178 Å
b = 7.9971 (7) Å	Cell parameters from 5359 reflections
c = 15.4939 (13) Å	θ = 5.6–72.4°
α = 98.105 (4)°	µ = 4.93 mm⁻¹
β = 94.316 (4)°	T = 150 K
γ = 95.002 (4)°	Block, light yellow
V = 799.54 (12) Å³	0.20 × 0.14 × 0.10 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2978 independent reflections
Radiation source: INCOATEC IµS micro-focus source	2744 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.030
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.4°, θ_min = 5.6°
ω scans	h = −8→8
Absorption correction: numerical (SADABS; Krause et al., 2015)	k = −9→9
T_min = 0.47, T_max = 0.65	l = −18→19
6131 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0424P)² + 0.4609P] where P = (F_o² + 2F_c²)/3
2978 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

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. 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 > 2sigma(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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

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

	x	y	z	U_iso*/U_eq
Cl1	1.46628 (8)	0.81960 (7)	0.07781 (3)	0.04020 (16)
Cl2	1.26553 (7)	0.65190 (6)	0.38541 (3)	0.03278 (15)
S1	0.56343 (7)	0.34226 (7)	0.16525 (3)	0.03124 (15)
O1	0.6855 (2)	0.3626 (2)	0.42004 (9)	0.0366 (4)
N1	0.4171 (2)	0.2189 (2)	0.33447 (10)	0.0271 (3)
N2	0.1980 (3)	0.0890 (3)	0.60834 (14)	0.0469 (5)
C1	0.3267 (3)	0.2389 (2)	0.17968 (13)	0.0267 (4)
C2	0.1860 (3)	0.2031 (3)	0.10570 (14)	0.0329 (4)
H2	0.221285	0.238965	0.052383	0.039*
C3	−0.0034 (3)	0.1162 (3)	0.10908 (14)	0.0354 (5)
H3	−0.097626	0.090518	0.058325	0.042*
C4	−0.0542 (3)	0.0669 (3)	0.18748 (15)	0.0346 (5)
H4	−0.184723	0.007778	0.190526	0.042*
C5	0.0823 (3)	0.1028 (3)	0.26120 (14)	0.0321 (4)
H5	0.043934	0.069093	0.314587	0.039*
C6	0.2759 (3)	0.1878 (2)	0.25857 (13)	0.0267 (4)
C7	0.5932 (3)	0.3289 (3)	0.34700 (13)	0.0279 (4)
C8	0.6774 (3)	0.4023 (2)	0.27150 (13)	0.0263 (4)
C9	0.8579 (3)	0.5003 (2)	0.29147 (13)	0.0281 (4)
H9	0.901779	0.520563	0.352193	0.034*
C10	0.9972 (3)	0.5804 (2)	0.23760 (13)	0.0269 (4)
C11	0.9552 (3)	0.5907 (3)	0.14823 (14)	0.0331 (4)
H11	0.824104	0.546039	0.120352	0.040*
C12	1.0964 (3)	0.6631 (3)	0.09939 (13)	0.0328 (4)
H12	1.063405	0.666462	0.038948	0.039*
C13	1.2868 (3)	0.7305 (3)	0.13960 (13)	0.0296 (4)
C14	1.3374 (3)	0.7275 (2)	0.22748 (13)	0.0294 (4)
H14	1.468043	0.775194	0.254682	0.035*
C15	1.1936 (3)	0.6535 (2)	0.27505 (13)	0.0267 (4)
C16	0.3685 (3)	0.1376 (3)	0.41071 (13)	0.0297 (4)
H16A	0.497966	0.120700	0.443893	0.036*
H16B	0.293516	0.024451	0.390173	0.036*
C17	0.2378 (3)	0.2424 (3)	0.47210 (13)	0.0324 (4)
H17A	0.307185	0.358366	0.490295	0.039*
H17B	0.102609	0.251541	0.441251	0.039*
C18	0.2103 (3)	0.1586 (3)	0.54900 (14)	0.0337 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0318 (3)	0.0578 (3)	0.0310 (3)	−0.0053 (2)	0.0060 (2)	0.0108 (2)
Cl2	0.0310 (3)	0.0415 (3)	0.0244 (3)	−0.00393 (19)	−0.00445 (18)	0.0084 (2)
S1	0.0251 (3)	0.0468 (3)	0.0203 (2)	−0.0039 (2)	0.00083 (17)	0.0050 (2)
O1	0.0377 (8)	0.0475 (9)	0.0219 (7)	−0.0087 (7)	−0.0026 (6)	0.0067 (6)
N1	0.0274 (8)	0.0318 (8)	0.0216 (8)	−0.0019 (6)	0.0014 (6)	0.0051 (6)
N2	0.0523 (13)	0.0529 (12)	0.0393 (12)	0.0016 (10)	0.0169 (9)	0.0153 (10)
C1	0.0224 (9)	0.0321 (10)	0.0250 (10)	0.0021 (7)	0.0026 (7)	0.0029 (8)
C2	0.0276 (10)	0.0446 (12)	0.0259 (10)	0.0036 (8)	0.0010 (8)	0.0035 (9)
C3	0.0271 (10)	0.0460 (12)	0.0299 (11)	−0.0001 (9)	−0.0024 (8)	−0.0003 (9)
C4	0.0260 (10)	0.0379 (11)	0.0371 (12)	−0.0031 (8)	0.0017 (8)	0.0006 (9)
C5	0.0308 (10)	0.0342 (10)	0.0307 (11)	−0.0018 (8)	0.0056 (8)	0.0041 (8)
C6	0.0255 (9)	0.0279 (9)	0.0256 (10)	0.0014 (7)	0.0010 (7)	0.0016 (8)
C7	0.0279 (10)	0.0325 (10)	0.0228 (10)	0.0007 (8)	0.0013 (7)	0.0037 (8)
C8	0.0256 (9)	0.0308 (9)	0.0220 (9)	0.0009 (7)	0.0015 (7)	0.0037 (7)
C9	0.0286 (10)	0.0327 (10)	0.0220 (9)	0.0005 (8)	0.0003 (7)	0.0037 (8)
C10	0.0260 (10)	0.0292 (9)	0.0253 (10)	0.0010 (7)	0.0016 (7)	0.0047 (8)
C11	0.0297 (10)	0.0418 (11)	0.0261 (10)	−0.0044 (8)	−0.0028 (8)	0.0071 (9)
C12	0.0326 (11)	0.0418 (11)	0.0235 (10)	−0.0020 (9)	−0.0010 (8)	0.0091 (8)
C13	0.0261 (10)	0.0349 (10)	0.0284 (10)	0.0005 (8)	0.0056 (8)	0.0067 (8)
C14	0.0241 (9)	0.0344 (10)	0.0290 (11)	0.0010 (8)	0.0006 (8)	0.0045 (8)
C15	0.0272 (10)	0.0291 (9)	0.0232 (9)	0.0019 (7)	−0.0012 (7)	0.0041 (7)
C16	0.0317 (10)	0.0331 (10)	0.0254 (10)	0.0003 (8)	0.0036 (8)	0.0095 (8)
C17	0.0358 (11)	0.0342 (10)	0.0273 (11)	−0.0006 (8)	0.0052 (8)	0.0063 (8)
C18	0.0335 (11)	0.0378 (11)	0.0296 (11)	−0.0002 (8)	0.0083 (8)	0.0033 (9)

Geometric parameters (Å, º) top

Cl1—C13	1.741 (2)	C7—C8	1.501 (3)
Cl2—C15	1.742 (2)	C8—C9	1.353 (3)
S1—C8	1.7407 (19)	C9—C10	1.452 (3)
S1—C1	1.7411 (19)	C9—H9	0.9500
O1—C7	1.226 (2)	C10—C11	1.407 (3)
N1—C7	1.375 (3)	C10—C15	1.415 (3)
N1—C6	1.421 (2)	C11—C12	1.380 (3)
N1—C16	1.469 (2)	C11—H11	0.9500
N2—C18	1.144 (3)	C12—C13	1.383 (3)
C1—C6	1.397 (3)	C12—H12	0.9500
C1—C2	1.397 (3)	C13—C14	1.381 (3)
C2—C3	1.380 (3)	C14—C15	1.384 (3)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.384 (3)	C16—C17	1.538 (3)
C3—H3	0.9500	C16—H16A	0.9900
C4—C5	1.378 (3)	C16—H16B	0.9900
C4—H4	0.9500	C17—C18	1.462 (3)
C5—C6	1.395 (3)	C17—H17A	0.9900
C5—H5	0.9500	C17—H17B	0.9900

Cl2···C18ⁱ	3.649 (2)	N2···H16A^ix	2.81
Cl2···C7ⁱⁱ	3.520 (2)	C2···C11^vi	3.569 (3)
Cl2···O1ⁱ	3.0269 (15)	C4···C12^x	3.577 (3)
Cl1···H2ⁱⁱⁱ	3.00	C4···C8^vi	3.490 (3)
Cl1···H4^iv	2.94	C5···C14^x	3.557 (3)
Cl2···H17Aⁱⁱ	3.06	C5···C17	3.352 (3)
Cl2···H9	2.51	C8···C4ⁱⁱ	3.490 (3)
Cl2···H16B^v	2.96	C9···C18^vii	3.497 (3)
S1···N1	3.1168 (17)	C11···C2ⁱⁱ	3.569 (3)
S1···C3ⁱⁱ	3.598 (2)	C12···C4^v	3.577 (3)
S1···C4ⁱⁱ	3.510 (2)	C14···C5^v	3.557 (3)
S1···C11	3.162 (2)	C17···C5	3.352 (3)
S1···C14^vi	3.578 (2)	C18···C9^vii	3.497 (3)
S1···H11	2.47	C5···H16B	2.53
O1···C17	3.210 (2)	C5···H17B	2.86
O1···Cl2ⁱ	3.0269 (15)	C8···H11	2.94
O1···C17^vii	3.336 (3)	C16···H5	2.48
O1···H17A	2.79	C17···H5	2.79
O1···H9	2.24	C18···H9^vii	2.98
O1···H16A	2.29	H2···H12^xi	2.49
O1···H17A^vii	2.45	H5···H16B	2.03
N2···C5^viii	3.282 (3)	H5···H17B	2.26
N2···H5^viii	2.43

C8—S1—C1	103.69 (9)	C11—C10—C15	115.36 (18)
C7—N1—C6	126.27 (16)	C11—C10—C9	125.21 (18)
C7—N1—C16	114.86 (16)	C15—C10—C9	119.43 (18)
C6—N1—C16	118.72 (16)	C12—C11—C10	122.73 (19)
C6—C1—C2	120.06 (18)	C12—C11—H11	118.6
C6—C1—S1	123.84 (15)	C10—C11—H11	118.6
C2—C1—S1	116.06 (15)	C11—C12—C13	119.12 (19)
C3—C2—C1	120.8 (2)	C11—C12—H12	120.4
C3—C2—H2	119.6	C13—C12—H12	120.4
C1—C2—H2	119.6	C14—C13—C12	121.32 (18)
C2—C3—C4	119.0 (2)	C14—C13—Cl1	119.49 (15)
C2—C3—H3	120.5	C12—C13—Cl1	119.19 (16)
C4—C3—H3	120.5	C13—C14—C15	118.53 (18)
C5—C4—C3	120.8 (2)	C13—C14—H14	120.7
C5—C4—H4	119.6	C15—C14—H14	120.7
C3—C4—H4	119.6	C14—C15—C10	122.93 (18)
C4—C5—C6	121.0 (2)	C14—C15—Cl2	116.72 (15)
C4—C5—H5	119.5	C10—C15—Cl2	120.34 (15)
C6—C5—H5	119.5	N1—C16—C17	112.76 (16)
C5—C6—C1	118.32 (18)	N1—C16—H16A	109.0
C5—C6—N1	120.22 (18)	C17—C16—H16A	109.0
C1—C6—N1	121.46 (17)	N1—C16—H16B	109.0
O1—C7—N1	119.47 (18)	C17—C16—H16B	109.0
O1—C7—C8	119.89 (18)	H16A—C16—H16B	107.8
N1—C7—C8	120.59 (17)	C18—C17—C16	108.89 (17)
C9—C8—C7	114.77 (17)	C18—C17—H17A	109.9
C9—C8—S1	123.67 (15)	C16—C17—H17A	109.9
C7—C8—S1	121.12 (14)	C18—C17—H17B	109.9
C8—C9—C10	132.12 (19)	C16—C17—H17B	109.9
C8—C9—H9	113.9	H17A—C17—H17B	108.3
C10—C9—H9	113.9	N2—C18—C17	176.4 (2)

C8—S1—C1—C6	−13.00 (19)	N1—C7—C8—S1	−3.4 (3)
C8—S1—C1—C2	168.95 (15)	C1—S1—C8—C9	−173.92 (17)
C6—C1—C2—C3	−0.4 (3)	C1—S1—C8—C7	14.09 (18)
S1—C1—C2—C3	177.68 (17)	C7—C8—C9—C10	173.6 (2)
C1—C2—C3—C4	1.0 (3)	S1—C8—C9—C10	1.1 (3)
C2—C3—C4—C5	−0.4 (3)	C8—C9—C10—C11	9.6 (4)
C3—C4—C5—C6	−0.7 (3)	C8—C9—C10—C15	−169.6 (2)
C4—C5—C6—C1	1.3 (3)	C15—C10—C11—C12	1.6 (3)
C4—C5—C6—N1	−178.01 (19)	C9—C10—C11—C12	−177.6 (2)
C2—C1—C6—C5	−0.7 (3)	C10—C11—C12—C13	−0.9 (3)
S1—C1—C6—C5	−178.69 (15)	C11—C12—C13—C14	−0.3 (3)
C2—C1—C6—N1	178.59 (18)	C11—C12—C13—Cl1	179.24 (17)
S1—C1—C6—N1	0.6 (3)	C12—C13—C14—C15	0.6 (3)
C7—N1—C6—C5	−165.80 (19)	Cl1—C13—C14—C15	−178.93 (15)
C16—N1—C6—C5	9.4 (3)	C13—C14—C15—C10	0.2 (3)
C7—N1—C6—C1	14.9 (3)	C13—C14—C15—Cl2	179.63 (15)
C16—N1—C6—C1	−169.86 (18)	C11—C10—C15—C14	−1.3 (3)
C6—N1—C7—O1	169.33 (18)	C9—C10—C15—C14	177.97 (18)
C16—N1—C7—O1	−6.1 (3)	C11—C10—C15—Cl2	179.34 (15)
C6—N1—C7—C8	−13.1 (3)	C9—C10—C15—Cl2	−1.4 (3)
C16—N1—C7—C8	171.47 (17)	C7—N1—C16—C17	88.6 (2)
O1—C7—C8—C9	1.4 (3)	C6—N1—C16—C17	−87.2 (2)
N1—C7—C8—C9	−176.09 (18)	N1—C16—C17—C18	−175.75 (17)
O1—C7—C8—S1	174.09 (16)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+2, −y+1, −z; (iv) x+2, y+1, z; (v) x+1, y+1, z; (vi) x−1, y, z; (vii) −x+1, −y+1, −z+1; (viii) −x, −y, −z+1; (ix) −x+1, −y, −z+1; (x) x−1, y−1, z; (xi) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N2^viii	0.95	2.43	3.282 (3)	149
C17—H17A···O1^vii	0.99	2.45	3.337 (3)	149

Symmetry codes: (vii) −x+1, −y+1, −z+1; (viii) −x, −y, −z+1.

Funding information

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged. TH is grateful to the Hacettepe University Scientific Research Project Unit (grant No. 013 D04 602 004) for support.

References

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