organic compounds
4-(4-Chlorophenyl)-1,2,3-selenadiazole
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
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
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.
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 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.
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 .
details are summarized in Table 2Structural data
CCDC reference: 1831319
https://doi.org/10.1107/S2414314618004625/bv4014sup1.cif
contains datablock I. DOI: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
Data collection: APEX2 (Bruker, 2008); cell
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).C8H5ClN2Se | F(000) = 472 |
Mr = 243.55 | Dx = 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 |
Bruker SMART APEXII CCD diffractometer | 1282 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.042 |
ω and φ scans | θmax = 26.6°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −13→12 |
Tmin = 0.543, Tmax = 0.654 | k = −17→17 |
11618 measured reflections | l = −6→7 |
1787 independent reflections |
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(Fo2) + (0.0166P)2 + 1.3536P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
1787 reflections | Δρmax = 0.33 e Å−3 |
109 parameters | Δρmin = −0.39 e Å−3 |
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 Uiso(H) = 1.5Ueq(C) for methyl H 1.2Ueq(C) for other H atoms. |
x | y | z | Uiso*/Ueq | ||
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) |
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) |
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) |
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
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.