4-{(4-Chloro­phen­yl)[4-(4-methyl­phen­yl)-1,2,3-selenadiazol-5-yl]meth­yl}-4,5,6,7-tetra­hydro-1,2,3-benzoselenadiazole

Muthukumaran, J.; Nishandhini, M.; Chitra, S.; Muthusubramanian, S.; Manisankar, P.; Bhattacharya, S.; Krishna, R.; Jeyakanthan, J.

doi:10.1107/S160053681101751X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1421-o1422

doi:10.1107/S160053681101751X

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4-{(4-Chlorophenyl)[4-(4-methylphenyl)-1,2,3-selenadiazol-5-yl]methyl}-4,5,6,7-tetrahydro-1,2,3-benzoselenadiazole

J. Muthukumaran,^a M. Nishandhini,^b S. Chitra,^c S. Muthusubramanian,^d P. Manisankar,^c Suman Bhattacharya,^e R. Krishna ^a ‡ and J. Jeyakanthan ^b ^*

^aCentre for Bioinformatics, School of Life Sciences, Pondicherry University, Puducherry 605 014, India, ^bDepartment of Bioinformatics, Alagappa University, Karaikudi 630 003, India, ^cDepartment of Industrial Chemistry, Alagappa University, Karaikudi 630 003, India, ^dDepartment of Organic Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and ^eDepartment of Chemistry, Pondicherry University, Puducherry 605 014, India
^*Correspondence e-mail: jjkanthan@gmail.com

(Received 5 April 2011; accepted 9 May 2011; online 14 May 2011)

In the title compound, C₂₂H₁₉ClN₄Se₂, the mean plane of the non-fused selenadiazole ring forms dihedral angles of 54.20 (16)° and 70.48 (11)°, respectively, with the essentially planar [maximum deviations of 0.025 (5) and 0.009 (2) Å, respectively] methylphenyl and chlorophenyl substituents. The tetrahydro-1,2,3-benzoselenadiazole group is disordered over two sets of sites with a refined occupancy ratio of 0.802 (5):0.198 (5). In the crystal, weak intermolecular C—H⋯N interactions are observed.

Related literature

For biological applications of 1,2,3-selenadiazole derivatives, see: Kuroda et al. (2001 ); El-Bahaie et al. (1990 ); El-Kashef et al. (1986 ); Plano et al. (2010 ); Padmavathi et al. (2002 ). For the structures of mono and bis-1,2,3-selenadiazole derivatives, see: Marx et al. (2008 ); Boag et al. (2010 ). For ring puckering analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₂H₁₉ClN₄Se₂
M_r = 532.78
Monoclinic, P 2₁ /c
a = 9.7226 (18) Å
b = 12.969 (4) Å
c = 17.690 (3) Å
β = 100.959 (19)°
V = 2189.9 (8) Å³
Z = 4
Mo Kα radiation
μ = 3.52 mm⁻¹
T = 293 K
0.4 × 0.3 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.516, T_max = 1.000
8795 measured reflections
3849 independent reflections
2590 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.138
S = 1.04
3849 reflections
255 parameters
293 restraints
H-atom parameters constrained
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.68 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6A—H6A⋯N2Aⁱ	0.98	2.57	3.517 (16)	164
C10—H10⋯N4ⁱⁱ	0.93	2.61	3.467 (7)	153
C12—H12⋯N3ⁱⁱⁱ	0.93	2.61	3.470 (7)	153
Symmetry codes: (i) -x+2, -y, -z; (ii) x-1, y, z; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681101751X/lh5230sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681101751X/lh5230Isup2.hkl

checkCIF report

Comment top

Selenium containing compounds like 1,2,3-selenadiazole are of increasing interest because of their unique chemical properties and have several important biological applications such as anti-fungal (Kuroda et al., 2001), anti-bacterial (El-Kashef et al.,1986), anti-microbial (El-Bahaie et al., 1990), anti-cancer (Plano et al., 2010) and insecticidal (Padmavathi et al., 2002) activities. In view of the growing importances of selenium containing compounds, we present herein the single-crystal structure of the title compound (I).

Some mono and bis-1,2,3-selenadiazole derivatives are already reported in the literature (Marx et al., 2008; Boag et al., 2010). The molecular structure of the title compound is shown in Fig. 1. The puckering analysis (Cremer & Pople, 1975) for the atoms C1A/C2A/C3A/C4A/C5A/C6A (belonging to the major component of disorder) of the 4,5,6,7-tetrahydrobenzo[d][1,2,3]selenadiazole group in (I) adopt an envelope conformation (E form) with puckering parameters of Q = 0.536 (8) Å, θ = 56.1 (8)° and Φ = 239.0 (10)°. The tetrahydro-1,2,3-benzoselenadiazole group is disordered with the refined site-occupancy ratios 0.802 (5):0.198 (5). The hetrocyclic ring (Se2/C14/C15/N3/N4) makes dihedral angles of 54.20 (16)° and 70.48 (11)°, respectively with the essentially planar atoms C16-C22 [maximum deviation 0.025 (5) Å for C16] and atoms C8-C13/Cl1 [maximum deviation of 0.009 (2)Å for Cl1]. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···N interactions.

Related literature top

For biological applications of 1,2,3-selenadiazole derivatives, see: Kuroda et al. (2001); El-Bahaie et al. (1990); El-Kashef et al. (1986); Plano et al. (2010); Padmavathi et al. (2002). For the structures of mono and bis-1,2,3-selenadiazole derivatives, see: Marx et al. (2008); Boag et al. (2010). For ring puckering analysis, see: Cremer & Pople (1975).

Experimental top

A mixture of 2-[1-(4-chloro-phenyl)-3-(4-methylphenyl)-3-oxopropyl]-1-cyclohexanone (1 mmol) and semicarbazide hydro-chloride (2.5 mmol) in ethanol (10 mL) was heated under reflux on a water bath for 3 h. After completion of the reaction as evident from TLC, the mixture was poured into ice-water (50 ml) and the resulting semicarbazone solid was filtered off. Then, a mixture of semicarbazone and SeO₂ (3 mmol) in tetrahydrofuran (THF) (10 ml) were refluxed on a water bath for 30 min. After completion of the reaction as monitored by TLC, the reaction mixture was filtered to remove selenium powder, the filtrate was concentrated under vacuum, and the residue was subjected to column chromatography using petroleum ether/ethyl acetate mixture (95:5; v/v) as eluent to afford the pure product. X-ray quality crystals were grown from a solution of the title compound in a 3:1 mixture of dichloromethane:ethylacetate in a partially closed 5ml glass vial over 7-8 days.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), showing displacement ellipsoids drawn at the 50% probability level. The disorder components are shown.
	Fig. 2. The crystal packing of (I) showing intermolecular interactions as dashed lines.

4-{(4-Chlorophenyl)[4-(4-methylphenyl)-1,2,3-selenadiazol-5-yl]methyl}-4,5,6,7- tetrahydro-1,2,3-benzoselenadiazole top

Crystal data top

C₂₂H₁₉ClN₄Se₂	F(000) = 1056
M_r = 532.78	D_x = 1.616 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2877 reflections
a = 9.7226 (18) Å	θ = 2.7–29.4°
b = 12.969 (4) Å	µ = 3.52 mm⁻¹
c = 17.690 (3) Å	T = 293 K
β = 100.959 (19)°	Block, blue
V = 2189.9 (8) Å³	0.4 × 0.3 × 0.2 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3849 independent reflections
Radiation source: fine-focus sealed tube	2590 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 15.9821 pixels mm^-1	θ_max = 25.0°, θ_min = 2.7°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −15→13
T_min = 0.516, T_max = 1.000	l = −20→21
8795 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0596P)² + 0.3633P] where P = (F_o² + 2F_c²)/3
3849 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 0.70 e Å⁻³
293 restraints	Δρ_min = −0.68 e Å⁻³

Crystal data top

C₂₂H₁₉ClN₄Se₂	V = 2189.9 (8) Å³
M_r = 532.78	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.7226 (18) Å	µ = 3.52 mm⁻¹
b = 12.969 (4) Å	T = 293 K
c = 17.690 (3) Å	0.4 × 0.3 × 0.2 mm
β = 100.959 (19)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3849 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2590 reflections with I > 2σ(I)
T_min = 0.516, T_max = 1.000	R_int = 0.041
8795 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	293 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.04	Δρ_max = 0.70 e Å⁻³
3849 reflections	Δρ_min = −0.68 e Å⁻³
255 parameters

Special details top

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.

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 > σ(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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Se2	1.09476 (5)	0.12061 (4)	0.16057 (3)	0.0585 (2)
Se1A	0.8917 (3)	0.22707 (11)	−0.19037 (8)	0.0718 (5)	0.802 (5)
N1A	1.0459 (4)	0.1859 (6)	−0.1174 (3)	0.0651 (10)	0.802 (5)
N2A	1.0132 (5)	0.1456 (10)	−0.0585 (4)	0.0651 (10)	0.802 (5)
C1A	0.8710 (5)	0.1372 (9)	−0.0608 (4)	0.0550 (7)	0.802 (5)
C2A	0.7819 (4)	0.1715 (6)	−0.1252 (2)	0.0550 (7)	0.802 (5)
C3A	0.6210 (4)	0.1768 (5)	−0.1395 (3)	0.0550 (7)	0.802 (5)
H3A1	0.5816	0.1386	−0.1857	0.066*	0.802 (5)
H3A2	0.5902	0.2478	−0.1464	0.066*	0.802 (5)
C4A	0.5716 (6)	0.1296 (5)	−0.0694 (3)	0.0550 (7)	0.802 (5)
H4A1	0.4790	0.1003	−0.0862	0.066*	0.802 (5)
H4A2	0.5637	0.1841	−0.0330	0.066*	0.802 (5)
C5A	0.6695 (6)	0.0453 (5)	−0.0280 (5)	0.0550 (7)	0.802 (5)
H5A1	0.6280	0.0150	0.0125	0.066*	0.802 (5)
H5A2	0.6802	−0.0087	−0.0644	0.066*	0.802 (5)
C6A	0.8145 (7)	0.0897 (9)	0.0070 (3)	0.0550 (7)	0.802 (5)
H6A	0.8761	0.0329	0.0284	0.066*	0.802 (5)
Se1B	0.9566 (8)	0.2149 (5)	−0.1767 (3)	0.0718 (5)	0.198 (5)
N1B	1.0899 (15)	0.176 (3)	−0.0914 (11)	0.0651 (10)	0.198 (5)
N2B	1.0313 (16)	0.139 (5)	−0.0400 (17)	0.0651 (10)	0.198 (5)
C1B	0.8867 (16)	0.136 (3)	−0.0542 (15)	0.0550 (7)	0.198 (5)
C2B	0.8184 (11)	0.179 (2)	−0.1217 (9)	0.0550 (7)	0.198 (5)
C3B	0.6665 (17)	0.150 (2)	−0.1572 (10)	0.0550 (7)	0.198 (5)
H3B1	0.6636	0.0825	−0.1811	0.066*	0.198 (5)
H3B2	0.6265	0.1999	−0.1961	0.066*	0.198 (5)
C4B	0.584 (2)	0.1489 (19)	−0.0911 (12)	0.0550 (7)	0.198 (5)
H4B1	0.5922	0.2149	−0.0647	0.066*	0.198 (5)
H4B2	0.4856	0.1352	−0.1107	0.066*	0.198 (5)
C5B	0.649 (2)	0.063 (2)	−0.0358 (17)	0.0550 (7)	0.198 (5)
H5B1	0.5952	0.0559	0.0050	0.066*	0.198 (5)
H5B2	0.6416	−0.0022	−0.0637	0.066*	0.198 (5)
C6B	0.803 (2)	0.083 (3)	0.0002 (14)	0.0550 (7)	0.198 (5)
H6B	0.8495	0.0184	0.0203	0.066*	0.198 (5)
C7	0.8116 (4)	0.1691 (3)	0.0701 (2)	0.0381 (10)
H7	0.7625	0.2297	0.0451	0.046*
Cl1	0.46832 (17)	0.03231 (15)	0.30184 (9)	0.0924 (6)
N3	1.1287 (4)	0.3213 (4)	0.1634 (2)	0.0590 (11)
C8	0.7283 (4)	0.1319 (4)	0.1297 (2)	0.0397 (11)
C14	0.9555 (4)	0.2050 (4)	0.1089 (2)	0.0398 (11)
C15	0.9973 (4)	0.3053 (4)	0.1179 (2)	0.0430 (11)
N4	1.1966 (4)	0.2421 (4)	0.1914 (3)	0.0694 (13)
C12	0.6800 (5)	0.0107 (4)	0.2241 (3)	0.0568 (13)
H12	0.7008	−0.0501	0.2517	0.068*
C16	0.9173 (5)	0.3976 (4)	0.0856 (2)	0.0431 (11)
C19	0.7582 (6)	0.5702 (5)	0.0261 (4)	0.0690 (16)
C9	0.6174 (5)	0.1898 (4)	0.1437 (3)	0.0525 (13)
H9	0.5960	0.2510	0.1166	0.063*
C11	0.5706 (5)	0.0717 (5)	0.2355 (3)	0.0596 (15)
C10	0.5379 (5)	0.1612 (5)	0.1956 (3)	0.0563 (14)
H10	0.4630	0.2016	0.2037	0.068*
C13	0.7581 (5)	0.0413 (4)	0.1711 (2)	0.0507 (12)
H13	0.8325	0.0004	0.1629	0.061*
C17	0.8653 (6)	0.4074 (4)	0.0074 (3)	0.0575 (14)
H17	0.8840	0.3561	−0.0259	0.069*
C18	0.7867 (6)	0.4917 (4)	−0.0218 (3)	0.0696 (16)
H18	0.7521	0.4959	−0.0745	0.084*
C21	0.8923 (6)	0.4772 (4)	0.1331 (3)	0.0576 (13)
H21	0.9291	0.4741	0.1855	0.069*
C20	0.8137 (6)	0.5610 (4)	0.1034 (3)	0.0709 (16)
H20	0.7975	0.6132	0.1367	0.085*
C22	0.6694 (7)	0.6612 (6)	−0.0055 (4)	0.115 (3)
H22A	0.6222	0.6878	0.0333	0.173*
H22B	0.6014	0.6399	−0.0495	0.173*
H22C	0.7280	0.7139	−0.0206	0.173*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se2	0.0497 (3)	0.0567 (4)	0.0679 (4)	0.0162 (3)	0.0084 (3)	0.0100 (3)
Se1A	0.0962 (12)	0.0770 (6)	0.0489 (5)	0.0015 (7)	0.0308 (7)	0.0137 (4)
N1A	0.077 (2)	0.060 (3)	0.069 (4)	0.018 (3)	0.038 (2)	0.015 (3)
N2A	0.077 (2)	0.060 (3)	0.069 (4)	0.018 (3)	0.038 (2)	0.015 (3)
C1A	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C2A	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C3A	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C4A	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C5A	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C6A	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
Se1B	0.0962 (12)	0.0770 (6)	0.0489 (5)	0.0015 (7)	0.0308 (7)	0.0137 (4)
N1B	0.077 (2)	0.060 (3)	0.069 (4)	0.018 (3)	0.038 (2)	0.015 (3)
N2B	0.077 (2)	0.060 (3)	0.069 (4)	0.018 (3)	0.038 (2)	0.015 (3)
C1B	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C2B	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C3B	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C4B	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C5B	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C6B	0.0730 (15)	0.0516 (16)	0.0431 (13)	−0.0072 (14)	0.0177 (12)	−0.0051 (10)
C7	0.041 (2)	0.038 (3)	0.035 (2)	0.007 (2)	0.009 (2)	0.0016 (19)
Cl1	0.0783 (10)	0.1362 (16)	0.0753 (9)	−0.0163 (10)	0.0468 (8)	−0.0029 (9)
N3	0.052 (2)	0.059 (3)	0.064 (3)	−0.003 (2)	0.004 (2)	−0.001 (2)
C8	0.034 (2)	0.047 (3)	0.038 (2)	0.004 (2)	0.0054 (19)	−0.004 (2)
C14	0.043 (2)	0.040 (3)	0.039 (2)	0.008 (2)	0.014 (2)	0.003 (2)
C15	0.036 (2)	0.048 (3)	0.045 (3)	0.006 (2)	0.010 (2)	−0.001 (2)
N4	0.045 (2)	0.085 (4)	0.076 (3)	0.006 (3)	0.006 (2)	0.008 (3)
C12	0.052 (3)	0.064 (4)	0.056 (3)	0.007 (3)	0.014 (3)	0.015 (3)
C16	0.041 (2)	0.043 (3)	0.048 (3)	0.003 (2)	0.013 (2)	0.002 (2)
C19	0.060 (3)	0.057 (4)	0.094 (4)	0.016 (3)	0.027 (3)	0.020 (3)
C9	0.042 (3)	0.063 (4)	0.052 (3)	0.011 (3)	0.007 (2)	−0.005 (2)
C11	0.042 (3)	0.092 (5)	0.047 (3)	−0.007 (3)	0.014 (2)	−0.009 (3)
C10	0.038 (3)	0.075 (4)	0.057 (3)	0.011 (3)	0.011 (2)	−0.014 (3)
C13	0.044 (3)	0.058 (3)	0.053 (3)	0.015 (3)	0.017 (2)	0.008 (2)
C17	0.070 (3)	0.048 (3)	0.055 (3)	0.000 (3)	0.014 (3)	0.005 (2)
C18	0.079 (4)	0.058 (4)	0.065 (3)	0.006 (4)	−0.003 (3)	0.020 (3)
C21	0.068 (3)	0.050 (3)	0.059 (3)	0.004 (3)	0.025 (3)	0.004 (3)
C20	0.085 (4)	0.058 (4)	0.082 (4)	0.021 (3)	0.046 (3)	0.004 (3)
C22	0.107 (6)	0.104 (6)	0.135 (6)	0.053 (5)	0.021 (5)	0.038 (5)

Geometric parameters (Å, º) top

Se2—C14	1.843 (4)	C5B—H5B2	0.9700
Se2—N4	1.886 (5)	C6B—C7	1.66 (4)
Se1A—C2A	1.8585 (10)	C6B—H6B	0.9800
Se1A—N1A	1.8605 (11)	C7—C14	1.510 (6)
N1A—N2A	1.2601 (10)	C7—C8	1.526 (6)
N2A—C1A	1.3790 (10)	C7—H7	0.9800
C1A—C2A	1.3688 (10)	Cl1—C11	1.753 (5)
C1A—C6A	1.5387 (10)	N3—N4	1.270 (6)
C2A—C3A	1.5385 (10)	N3—C15	1.390 (6)
C3A—C4A	1.5394 (10)	C8—C9	1.375 (6)
C3A—H3A1	0.9700	C8—C13	1.386 (6)
C3A—H3A2	0.9700	C14—C15	1.363 (6)
C4A—C5A	1.5396 (10)	C15—C16	1.482 (6)
C4A—H4A1	0.9700	C12—C11	1.371 (7)
C4A—H4A2	0.9700	C12—C13	1.372 (6)
C5A—C6A	1.5394 (10)	C12—H12	0.9300
C5A—H5A1	0.9700	C16—C21	1.381 (6)
C5A—H5A2	0.9700	C16—C17	1.385 (6)
C6A—C7	1.523 (11)	C19—C20	1.377 (8)
C6A—H6A	0.9800	C19—C18	1.387 (8)
Se1B—C2B	1.8597 (11)	C19—C22	1.506 (8)
Se1B—N1B	1.8602 (11)	C9—C10	1.360 (7)
N1B—N2B	1.2600 (10)	C9—H9	0.9300
N2B—C1B	1.3798 (10)	C11—C10	1.364 (7)
C1B—C2B	1.3698 (10)	C10—H10	0.9300
C1B—C6B	1.5397 (10)	C13—H13	0.9300
C2B—C3B	1.5398 (11)	C17—C18	1.377 (7)
C3B—C4B	1.5399 (10)	C17—H17	0.9300
C3B—H3B1	0.9700	C18—H18	0.9300
C3B—H3B2	0.9700	C21—C20	1.373 (7)
C4B—C5B	1.5398 (10)	C21—H21	0.9300
C4B—H4B1	0.9700	C20—H20	0.9300
C4B—H4B2	0.9700	C22—H22A	0.9600
C5B—C6B	1.5398 (11)	C22—H22B	0.9600
C5B—H5B1	0.9700	C22—H22C	0.9600

C14—Se2—N4	86.7 (2)	C5B—C6B—C7	109 (3)
C2A—Se1A—N1A	86.59 (18)	C1B—C6B—H6B	110.6
N2A—N1A—Se1A	113.4 (3)	C5B—C6B—H6B	110.6
N1A—N2A—C1A	114.7 (4)	C7—C6B—H6B	110.6
C2A—C1A—N2A	118.1 (4)	C14—C7—C6A	113.4 (4)
C2A—C1A—C6A	121.0 (4)	C14—C7—C8	110.6 (3)
N2A—C1A—C6A	120.9 (4)	C6A—C7—C8	112.3 (4)
C1A—C2A—C3A	127.9 (3)	C14—C7—C6B	117.2 (8)
C1A—C2A—Se1A	107.2 (3)	C8—C7—C6B	110.1 (7)
C3A—C2A—Se1A	124.6 (3)	C14—C7—H7	106.7
C2A—C3A—C4A	108.3 (3)	C6A—C7—H7	106.7
C2A—C3A—H3A1	110.0	C8—C7—H7	106.7
C4A—C3A—H3A1	110.0	C6B—C7—H7	104.9
C2A—C3A—H3A2	110.0	N4—N3—C15	117.2 (4)
C4A—C3A—H3A2	110.0	C9—C8—C13	117.4 (4)
H3A1—C3A—H3A2	108.4	C9—C8—C7	119.3 (4)
C3A—C4A—C5A	113.9 (5)	C13—C8—C7	123.3 (4)
C3A—C4A—H4A1	108.8	C15—C14—C7	125.3 (4)
C5A—C4A—H4A1	108.8	C15—C14—Se2	109.5 (3)
C3A—C4A—H4A2	108.8	C7—C14—Se2	124.9 (3)
C5A—C4A—H4A2	108.8	C14—C15—N3	115.6 (4)
H4A1—C4A—H4A2	107.7	C14—C15—C16	127.1 (4)
C6A—C5A—C4A	111.2 (5)	N3—C15—C16	117.4 (4)
C6A—C5A—H5A1	109.4	N3—N4—Se2	111.0 (3)
C4A—C5A—H5A1	109.4	C11—C12—C13	118.6 (5)
C6A—C5A—H5A2	109.4	C11—C12—H12	120.7
C4A—C5A—H5A2	109.4	C13—C12—H12	120.7
H5A1—C5A—H5A2	108.0	C21—C16—C17	117.7 (5)
C7—C6A—C1A	111.1 (8)	C21—C16—C15	120.7 (4)
C7—C6A—C5A	113.9 (7)	C17—C16—C15	121.6 (4)
C1A—C6A—C5A	105.8 (5)	C20—C19—C18	117.2 (5)
C7—C6A—H6A	108.7	C20—C19—C22	121.8 (6)
C1A—C6A—H6A	108.7	C18—C19—C22	121.0 (6)
C5A—C6A—H6A	108.7	C10—C9—C8	122.6 (5)
C2B—Se1B—N1B	88.3 (7)	C10—C9—H9	118.7
N2B—N1B—Se1B	110.4 (11)	C8—C9—H9	118.7
N1B—N2B—C1B	117.5 (14)	C10—C11—C12	121.7 (5)
C2B—C1B—N2B	117.3 (12)	C10—C11—Cl1	119.2 (4)
C2B—C1B—C6B	120.3 (12)	C12—C11—Cl1	119.0 (5)
N2B—C1B—C6B	122.3 (14)	C9—C10—C11	118.4 (5)
C1B—C2B—C3B	121.5 (15)	C9—C10—H10	120.8
C1B—C2B—Se1B	106.1 (9)	C11—C10—H10	120.8
C3B—C2B—Se1B	125.5 (11)	C12—C13—C8	121.2 (4)
C2B—C3B—C4B	106.9 (12)	C12—C13—H13	119.4
C2B—C3B—H3B1	110.3	C8—C13—H13	119.4
C4B—C3B—H3B1	110.3	C18—C17—C16	121.3 (5)
C2B—C3B—H3B2	110.3	C18—C17—H17	119.4
C4B—C3B—H3B2	110.3	C16—C17—H17	119.4
H3B1—C3B—H3B2	108.6	C17—C18—C19	121.0 (5)
C5B—C4B—C3B	106.3 (15)	C17—C18—H18	119.5
C5B—C4B—H4B1	110.5	C19—C18—H18	119.5
C3B—C4B—H4B1	110.5	C20—C21—C16	120.6 (5)
C5B—C4B—H4B2	110.5	C20—C21—H21	119.7
C3B—C4B—H4B2	110.5	C16—C21—H21	119.7
H4B1—C4B—H4B2	108.7	C21—C20—C19	122.2 (5)
C6B—C5B—C4B	112.9 (16)	C21—C20—H20	118.9
C6B—C5B—H5B1	109.0	C19—C20—H20	118.9
C4B—C5B—H5B1	109.0	C19—C22—H22A	109.5
C6B—C5B—H5B2	109.0	C19—C22—H22B	109.5
C4B—C5B—H5B2	109.0	H22A—C22—H22B	109.5
H5B1—C5B—H5B2	107.8	C19—C22—H22C	109.5
C1B—C6B—C5B	114.0 (14)	H22A—C22—H22C	109.5
C1B—C6B—C7	102 (3)	H22B—C22—H22C	109.5

C2A—Se1A—N1A—N2A	−2.8 (7)	C5B—C6B—C7—C6A	−177 (17)
Se1A—N1A—N2A—C1A	1.9 (13)	C1B—C6B—C7—C8	177.6 (12)
N1A—N2A—C1A—C2A	0.5 (17)	C5B—C6B—C7—C8	56.9 (16)
N1A—N2A—C1A—C6A	−179.9 (10)	C14—C7—C8—C9	109.2 (4)
N2A—C1A—C2A—C3A	−175.9 (10)	C6A—C7—C8—C9	−123.1 (5)
C6A—C1A—C2A—C3A	4.5 (16)	C6B—C7—C8—C9	−119.7 (11)
N2A—C1A—C2A—Se1A	−2.6 (14)	C14—C7—C8—C13	−71.1 (5)
C6A—C1A—C2A—Se1A	177.8 (9)	C6A—C7—C8—C13	56.7 (6)
N1A—Se1A—C2A—C1A	2.8 (7)	C6B—C7—C8—C13	60.0 (12)
N1A—Se1A—C2A—C3A	176.3 (7)	C6A—C7—C14—C15	127.4 (5)
C1A—C2A—C3A—C4A	−3.4 (12)	C8—C7—C14—C15	−105.5 (5)
Se1A—C2A—C3A—C4A	−175.6 (5)	C6B—C7—C14—C15	127.3 (10)
C2A—C3A—C4A—C5A	−29.7 (8)	C6A—C7—C14—Se2	−59.8 (5)
C3A—C4A—C5A—C6A	64.0 (7)	C8—C7—C14—Se2	67.3 (4)
C2A—C1A—C6A—C7	−97.8 (10)	C6B—C7—C14—Se2	−59.9 (10)
N2A—C1A—C6A—C7	82.7 (14)	N4—Se2—C14—C15	1.2 (3)
C2A—C1A—C6A—C5A	26.3 (14)	N4—Se2—C14—C7	−172.6 (4)
N2A—C1A—C6A—C5A	−153.3 (12)	C7—C14—C15—N3	172.5 (4)
C4A—C5A—C6A—C7	64.0 (7)	Se2—C14—C15—N3	−1.2 (5)
C4A—C5A—C6A—C1A	−58.3 (10)	C7—C14—C15—C16	−6.5 (7)
C2B—Se1B—N1B—N2B	5 (3)	Se2—C14—C15—C16	179.8 (3)
Se1B—N1B—N2B—C1B	−2 (5)	N4—N3—C15—C14	0.5 (6)
N1B—N2B—C1B—C2B	−3 (7)	N4—N3—C15—C16	179.6 (4)
N1B—N2B—C1B—C6B	174 (4)	C15—N3—N4—Se2	0.5 (5)
N2B—C1B—C2B—C3B	158 (4)	C14—Se2—N4—N3	−1.0 (4)
C6B—C1B—C2B—C3B	−18 (6)	C14—C15—C16—C21	125.1 (5)
N2B—C1B—C2B—Se1B	6 (5)	N3—C15—C16—C21	−53.8 (6)
C6B—C1B—C2B—Se1B	−170 (4)	C14—C15—C16—C17	−55.1 (7)
N1B—Se1B—C2B—C1B	−6 (3)	N3—C15—C16—C17	126.0 (5)
N1B—Se1B—C2B—C3B	−157 (3)	C13—C8—C9—C10	−0.2 (7)
C1B—C2B—C3B—C4B	45 (4)	C7—C8—C9—C10	179.5 (4)
Se1B—C2B—C3B—C4B	−169 (2)	C13—C12—C11—C10	0.1 (8)
C2B—C3B—C4B—C5B	−64 (2)	C13—C12—C11—Cl1	179.0 (4)
C3B—C4B—C5B—C6B	63 (3)	C8—C9—C10—C11	0.5 (7)
C2B—C1B—C6B—C5B	12 (6)	C12—C11—C10—C9	−0.4 (8)
N2B—C1B—C6B—C5B	−164 (5)	Cl1—C11—C10—C9	−179.3 (4)
C2B—C1B—C6B—C7	−105 (4)	C11—C12—C13—C8	0.1 (7)
N2B—C1B—C6B—C7	79 (5)	C9—C8—C13—C12	−0.1 (7)
C4B—C5B—C6B—C1B	−36 (5)	C7—C8—C13—C12	−179.8 (4)
C4B—C5B—C6B—C7	77 (2)	C21—C16—C17—C18	−2.6 (7)
C1A—C6A—C7—C14	−65.9 (6)	C15—C16—C17—C18	177.6 (5)
C5A—C6A—C7—C14	174.8 (4)	C16—C17—C18—C19	0.8 (9)
C1A—C6A—C7—C8	167.9 (4)	C20—C19—C18—C17	1.1 (9)
C5A—C6A—C7—C8	48.6 (7)	C22—C19—C18—C17	−178.6 (6)
C1A—C6A—C7—C6B	112 (16)	C17—C16—C21—C20	2.6 (8)
C5A—C6A—C7—C6B	−7 (16)	C15—C16—C21—C20	−177.6 (5)
C1B—C6B—C7—C14	−54.9 (18)	C16—C21—C20—C19	−0.8 (9)
C5B—C6B—C7—C14	−175.7 (10)	C18—C19—C20—C21	−1.1 (9)
C1B—C6B—C7—C6A	−57 (15)	C22—C19—C20—C21	178.6 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6A—H6A···N2Aⁱ	0.98	2.57	3.517 (16)	164
C10—H10···N4ⁱⁱ	0.93	2.61	3.467 (7)	153
C12—H12···N3ⁱⁱⁱ	0.93	2.61	3.470 (7)	153

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₉ClN₄Se₂
M_r	532.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.7226 (18), 12.969 (4), 17.690 (3)
β (°)	100.959 (19)
V (Å³)	2189.9 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.52
Crystal size (mm)	0.4 × 0.3 × 0.2

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.516, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8795, 3849, 2590
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.138, 1.04
No. of reflections	3849
No. of parameters	255
No. of restraints	293
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.68

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6A—H6A···N2Aⁱ	0.98	2.57	3.517 (16)	164
C10—H10···N4ⁱⁱ	0.93	2.61	3.467 (7)	153
C12—H12···N3ⁱⁱⁱ	0.93	2.61	3.470 (7)	153

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

Footnotes

‡Additional correspondence author, e-mail: krishstrucbio@gmail.com.

Acknowledgements

RK and JM thank the Centre for Bioinformatics (funded by the Department of Biotechnology and the Department of Information Technology, New Delhi, India), Pondicherry University and JJ thanks the Department of Organic Chemistry, Madurai Kamaraj University, for providing the facilities for the synthesis of the title compound, and the Department of Bioinformatics, Alagappa University for providing the computational facilities to carry out this research work. JJ also thanks Binoy Krishna Saha, Assistant Professor, Department of Chemistry, Pondicherry University, for providing the X-ray facility. JM also thanks the Council for Scientific and Industrial Research (CSIR) for a Senior Research Fellowship (SRF).

References

Boag, N. M., Jackson, A. D., Lickiss, P. D., Pilkington, R. D. & Redhouse, A. D. (2010). Acta Cryst. E66, m241. Web of Science CrossRef IUCr Journals Google Scholar
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El-Kashef, H. S., E-Bayoumy, B. & Aly, T. I. (1986). Egypt. J. Pharm. Sci. 27, 27–30. CAS Google Scholar
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Volume 67| Part 6| June 2011| Pages o1421-o1422

doi:10.1107/S160053681101751X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-{(4-Chloro­phen­yl)[4-(4-methyl­phen­yl)-1,2,3-selena­diazol-5-yl]meth­yl}-4,5,6,7-tetra­hydro-1,2,3-benzoselena­diazole

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

4-{(4-Chlorophenyl)[4-(4-methylphenyl)-1,2,3-selenadiazol-5-yl]methyl}-4,5,6,7-tetrahydro-1,2,3-benzoselenadiazole