4-(4-Chloro­phen­yl)-1,2,3-selena­diazole

Ravichandran, K.; Ranjith, S.; Sankari, S.; Beemarao, M.o; Ponnuswamy, M.N.

doi:10.1107/S2414314618004625

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 3| March 2018| x180462

https://doi.org/10.1107/S2414314618004625

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4-(4-Chlorophenyl)-1,2,3-selenadiazole

K. Ravichandran,^a S. Ranjith,^b S. Sankari,^c M. Beemarao ^a and M. N. Ponnuswamy ^d ^*

^aDepartment of Physics, Kandaswami Kandar's College, Velur, Namakkal 638 182, India, ^bDepartment of Physics, SRM Institute of Science and Technology, Ramapuram Campus, Chennai, India, ^cDepartment of Chemistry, Sri Sarada College for Women (Autonomous), Fairlands, Salem 600 016, India, and ^dCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: mnpsy2004@yahoo.com

Edited by R. J. Butcher, Howard University, USA (Received 9 February 2018; accepted 21 March 2018; online 27 March 2018)

In the title compound, C₈H₅ClN₂Se, the dihedral angle between the planes of the selenadiazole and chlorophenyl rings is 16.6 (2)°. In the crystal, the packing of the molecules is consolidated by weak C—H⋯N hydrogen bonds, which generate [001] chains, and π–π stacking interactions are observed between the phenyl and selenadiazole rings, with a centroid–centroid distance of 3.884 (2) Å. There is also a short Se⋯Cl contact of 3.468 (1) Å

Keywords: crystal structure; phenylselenadiaxole; π–π stacking interactions.

CCDC reference: 1831319

Structure description

Selenium-containing compounds, such as 1,2,3-selenadiazoles, are of increasing interest owing to their chemical properties and biological applications, such as anti-bacterial, anti-microbial, anticancer and insecticidal activities (El-Kashef et al., 1986 ; Khanna, 2005 ). Selenadiazoles are the important class of organoselenium compounds utilized in the synthesis of semiconductor nanoparticles (Padmavathi et al., 2002 ). As part of our studies in this area, the structure of title compound has been determined.

The ORTEP plot of the molecule is shown in Fig. 1. The selenadiazole ring makes a dihedral angle of 16.6 (2)° with the chlorophenyl ring.

Figure 1
The molecular structure of the title compound, showing the atomic numbering scheme and displacement ellipsoids drawn at the 30% probability level.

In the crystal, the packing of the molecules is consolidated by weak C—H⋯N hydrogen bonds (see Table 1), which generate [001] chains. There is also a short Se12⋯Cl1 contact of 3.468 (1) Å. The crystal structure is further augmented by π–π interactions between adjacent selenium and phenyl rings as shown in Fig. 2, with a centroid–centroid distance of 3.884 (2) Å.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N2ⁱ	0.93	2.62	3.528 (5)	164
Symmetry code: (i) x, y, z+1.

Figure 2
The π–π interactions between adjacent selenium and phenyl rings for the asymmetric molecule and its partner.

Synthesis and crystallization

The title compound was synthesized according to the procedure of Baliah & Rangarajan, (1954 )and colourless block-shaped crystals were recrystallized from a petroleum ether–ethyl acetate solvent mixture.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₈H₅ClN₂Se
M_r	243.55
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.3353 (9), 14.0058 (12), 5.9540 (4)
β (°)	97.320 (3)
V (Å³)	854.84 (12)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	4.64
Crystal size (mm)	0.15 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008 )
T_min, T_max	0.543, 0.654
No. of measured, independent and observed [I > 2σ(I)] reflections	11618, 1787, 1282
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.630

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.079, 1.07
No. of reflections	1787
No. of parameters	109
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.39
Computer programs: APEX2 and SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008 ), SHELXL2018/1 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1831319

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618004625/bv4014sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618004625/bv4014Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618004625/bv4014Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/1 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

4-(4-Chlorophenyl)-1,2,3-selenadiazole top

Crystal data top

C₈H₅ClN₂Se	F(000) = 472
M_r = 243.55	D_x = 1.892 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.3353 (9) Å	Cell parameters from 1286 reflections
b = 14.0058 (12) Å	θ = 2.0–26.6°
c = 5.9540 (4) Å	µ = 4.64 mm⁻¹
β = 97.320 (3)°	T = 296 K
V = 854.84 (12) Å³	Block, colorless
Z = 4	0.15 × 0.15 × 0.10 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	1282 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.042
ω and φ scans	θ_max = 26.6°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→12
T_min = 0.543, T_max = 0.654	k = −17→17
11618 measured reflections	l = −6→7
1787 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.079	w = 1/[σ²(F_o²) + (0.0166P)² + 1.3536P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
1787 reflections	Δρ_max = 0.33 e Å⁻³
109 parameters	Δρ_min = −0.39 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. H atoms were positioned geometrically (N—H=0.88–0.90 Å and C—H=0.93–0.98 Å) and allowed to ride on their parent atoms,with U_iso(H) = 1.5U_eq(C) for methyl H 1.2U_eq(C) for other H atoms.

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

	x	y	z	U_iso*/U_eq
C4	0.4016 (4)	0.3768 (2)	0.3085 (5)	0.0370 (8)
C5	0.2945 (4)	0.3664 (3)	0.4154 (6)	0.0497 (9)
H5	0.297028	0.360609	0.571528	0.060*
C6	0.5378 (3)	0.3794 (2)	0.4058 (5)	0.0357 (8)
C7	0.6334 (4)	0.4123 (3)	0.2806 (6)	0.0447 (9)
H7	0.608413	0.435267	0.134966	0.054*
C8	0.7636 (4)	0.4121 (3)	0.3649 (6)	0.0492 (10)
H8	0.826132	0.434318	0.278261	0.059*
C9	0.7990 (4)	0.3782 (3)	0.5809 (6)	0.0475 (10)
C10	0.7070 (4)	0.3464 (3)	0.7105 (6)	0.0514 (10)
H10	0.732189	0.324180	0.856660	0.062*
C11	0.5777 (4)	0.3478 (3)	0.6230 (6)	0.0471 (10)
H11	0.515632	0.326863	0.712024	0.057*
N2	0.2534 (3)	0.3807 (3)	−0.0063 (5)	0.0589 (9)
N3	0.3723 (3)	0.3846 (2)	0.0764 (5)	0.0507 (8)
Se1	0.14713 (4)	0.36506 (3)	0.22008 (7)	0.05959 (17)
Cl12	0.96352 (11)	0.37587 (10)	0.6907 (2)	0.0761 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C4	0.048 (2)	0.033 (2)	0.0305 (17)	−0.0043 (16)	0.0080 (15)	−0.0008 (15)
C5	0.053 (2)	0.057 (2)	0.039 (2)	−0.006 (2)	0.0058 (18)	−0.0015 (19)
C6	0.043 (2)	0.0322 (19)	0.0322 (18)	−0.0001 (15)	0.0058 (15)	−0.0028 (14)
C7	0.048 (2)	0.051 (2)	0.035 (2)	−0.0035 (19)	0.0031 (17)	0.0054 (17)
C8	0.040 (2)	0.060 (3)	0.048 (2)	−0.0045 (19)	0.0066 (18)	0.0065 (19)
C9	0.043 (2)	0.052 (3)	0.046 (2)	0.0072 (19)	0.0002 (18)	−0.0043 (18)
C10	0.058 (3)	0.057 (3)	0.038 (2)	0.010 (2)	−0.0018 (19)	0.0077 (18)
C11	0.049 (2)	0.054 (3)	0.040 (2)	0.0010 (18)	0.0113 (18)	0.0072 (17)
N2	0.050 (2)	0.083 (3)	0.0423 (19)	−0.0076 (18)	−0.0005 (16)	0.0051 (17)
N3	0.044 (2)	0.072 (2)	0.0366 (17)	−0.0066 (17)	0.0060 (14)	0.0065 (15)
Se1	0.0458 (3)	0.0782 (3)	0.0553 (3)	−0.0081 (2)	0.00855 (19)	−0.0042 (2)
Cl12	0.0480 (7)	0.1104 (10)	0.0663 (7)	0.0161 (6)	−0.0065 (5)	0.0029 (7)

Geometric parameters (Å, º) top

C4—C5	1.353 (5)	C8—C9	1.376 (5)
C4—N3	1.381 (4)	C8—H8	0.9300
C4—C6	1.454 (5)	C9—C10	1.372 (5)
C5—Se1	1.795 (4)	C9—Cl12	1.742 (4)
C5—H5	0.9300	C10—C11	1.371 (5)
C6—C11	1.380 (5)	C10—H10	0.9300
C6—C7	1.390 (5)	C11—H11	0.9300
C7—C8	1.376 (5)	N2—N3	1.265 (4)
C7—H7	0.9300	N2—Se1	1.857 (3)

C5—C4—N3	113.1 (3)	C9—C8—H8	120.9
C5—C4—C6	128.6 (3)	C10—C9—C8	121.1 (4)
N3—C4—C6	118.3 (3)	C10—C9—Cl12	119.7 (3)
C4—C5—Se1	111.9 (3)	C8—C9—Cl12	119.2 (3)
C4—C5—H5	124.0	C11—C10—C9	119.6 (4)
Se1—C5—H5	124.0	C11—C10—H10	120.2
C11—C6—C7	117.5 (3)	C9—C10—H10	120.2
C11—C6—C4	121.6 (3)	C10—C11—C6	121.4 (4)
C7—C6—C4	120.9 (3)	C10—C11—H11	119.3
C8—C7—C6	122.2 (3)	C6—C11—H11	119.3
C8—C7—H7	118.9	N3—N2—Se1	111.0 (2)
C6—C7—H7	118.9	N2—N3—C4	117.6 (3)
C7—C8—C9	118.2 (3)	C5—Se1—N2	86.42 (16)
C7—C8—H8	120.9

N3—C4—C5—Se1	0.5 (4)	C8—C9—C10—C11	0.5 (6)
C6—C4—C5—Se1	−178.7 (3)	Cl12—C9—C10—C11	−179.6 (3)
C5—C4—C6—C11	16.3 (6)	C9—C10—C11—C6	0.7 (6)
N3—C4—C6—C11	−162.8 (3)	C7—C6—C11—C10	−1.6 (5)
C5—C4—C6—C7	−165.0 (4)	C4—C6—C11—C10	177.1 (3)
N3—C4—C6—C7	15.9 (5)	Se1—N2—N3—C4	0.1 (4)
C11—C6—C7—C8	1.4 (5)	C5—C4—N3—N2	−0.4 (5)
C4—C6—C7—C8	−177.4 (3)	C6—C4—N3—N2	178.9 (3)
C6—C7—C8—C9	−0.2 (6)	C4—C5—Se1—N2	−0.3 (3)
C7—C8—C9—C10	−0.8 (6)	N3—N2—Se1—C5	0.1 (3)
C7—C8—C9—Cl12	179.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N2ⁱ	0.93	2.62	3.528 (5)	164

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

Acknowledgements

The authors thank the TBI consultancy, University of Madras, India, for the data collection

References

Baliah, V. & Rangarajan, T. (1954). J. Chem. Soc. pp. 3068–3070. CrossRef Web of Science Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
El-Kashef, H. S., E-Bayoumy, B. & Aly, T. I. (1986). Egypt. J. Pharm. Sci. 27, 27–30. CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Khanna, P. K. (2005). Phosphorus Sulfur Silicon Relat. Elem. 180, 951–955. Web of Science CrossRef CAS Google Scholar
Padmavathi, V., Sumathi, R. P. & Padmaja, A. (2002). J. Ecobiol. 14, 9–12. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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