PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o349.
Published online 2008 January 4. doi:  10.1107/S1600536807067487
PMCID: PMC2960371

4-(4-Chloro­phen­yl)-5-[1-(4-chloro­phenyl)-2-methyl-2-nitro­prop­yl]-1,2,3-selenadiazole

Abstract

In the title compound, C18H15Cl2N3O2Se, the selenadiazole ring makes dihedral angles of 49.87 (3) and 55.70 (3)° with the two benzene rings. The dihedral angle between the two benzene rings is 11.90 (5)°. In the crystal structure, intra­molecular C—H(...)O and C—H(...)Se inter­actions and inter­molecular C—H(...)O, C—H(...)Cl and C—H(...)N inter­actions are observed.

Related literature

For related literature, see: Bertini et al. (1984 [triangle]); El-Bahaie et al. (1990 [triangle]); El-Kashef et al. (1986 [triangle]); Kuroda et al. (2001 [triangle]); Mellini & Merlino (1976a [triangle],b [triangle]); Padmavathi et al. (2002 [triangle]); Saravanan et al. (2006 [triangle]); Gunasekaran et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o349-scheme1.jpg

Experimental

Crystal data

  • C18H15Cl2N3O2Se
  • M r = 455.19
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o349-efi1.jpg
  • a = 7.8352 (2) Å
  • b = 10.9208 (3) Å
  • c = 11.5507 (3) Å
  • α = 75.381 (1)°
  • β = 89.044 (1)°
  • γ = 83.331 (1)°
  • V = 949.80 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 2.27 mm−1
  • T = 100 (2) K
  • 0.33 × 0.18 × 0.17 mm

Data collection

  • Bruker Kappa APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2004 [triangle]) T min = 0.507, T max = 0.679
  • 44785 measured reflections
  • 9335 independent reflections
  • 8074 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.026
  • wR(F 2) = 0.064
  • S = 1.03
  • 9335 reflections
  • 237 parameters
  • H-atom parameters constrained
  • Δρmax = 0.57 e Å−3
  • Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807067487/is2267sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067487/is2267Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Selenium containing compounds like 1,2,3-selenadiazole possess various beneficial activities like antifungal (Kuroda et al., 2001), antibacterial (El-Kashef et al., 1986), antimicrobial (El-Bahaie et al., 1990) and insecticidal (Padmavathi et al., 2002) activities. As naturally occurring nitro compounds exhibit broad antibiotic activity and certain alkyl nitro compounds exhibit antitumor activity, it was decided to synthesize and structurally characterize a set of 1,2,3-selenadiazoles with nitro group in the side chain (Saravanan et al., 2006).

The geometric parameters in the compound, (I) agree with the reported values of similar structure (Mellini & Merlino, 1976a,b; Bertini et al., 1984; Gunasekaran et al., 2007). The C3—C8 benzene ring makes a dihedral angle of 49.87 (3)° with the heterocyclic ring and the C10—C15 benzene ring makes a dihedral angle of 55.70 (3)° with the heterocyclic ring (Fig. 1).

The details of the hydrogen bonding are given in Table 1. The molecular structure is stabilized by weak intramolecular C—H···O and C—H···Se interactions and the crystal packing is stabilized by weak intermolecular C—H···O, C—H···Cl and C—H···N interactions (Fig. 2).

Experimental

A solution of 2-[1,3-bis(4-chlorophenyl)-4-methyl-4-nitropentylidene]-1-hydrazine carboxamide (0.005 mol) and powdered selenium dioxide (0.05 mol) in dry THF was gently heated on a water bath for 2 h. The selenium deposited on cooling was removed by filtration, and the filtrate was poured into crushed ice, extracted with chloroform, and purified by column chromatography using silica gel (60–120 mesh) with 97:3 petroleum ether: ethyl acetate as eluent to give 4-(4-chlorophenyl)-5-[1-(4-chlorophenyl)-2-methyl-2- nitropropyl]-1,2,3-selenadiazole. Solvent used for crystallization is ethanol.

Refinement

H atoms were positioned geometrically and refined using riding model, with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.98 Å and Uiso(H) = 1.5Ueq(C) for CH3, C—H = 1.00 Å and Uiso(H) = 1.2Ueq(C) for CH.

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The packing of (I), viewed down the b axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

Crystal data

C18H15Cl2N3O2SeZ = 2
Mr = 455.19F000 = 456
Triclinic, P1Dx = 1.592 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 7.8352 (2) ÅCell parameters from 8302 reflections
b = 10.9208 (3) Åθ = 2.7–34.5º
c = 11.5507 (3) ŵ = 2.28 mm1
α = 75.381 (1)ºT = 100 (2) K
β = 89.044 (1)ºRectangular, colourless
γ = 83.331 (1)º0.33 × 0.18 × 0.17 mm
V = 949.80 (4) Å3

Data collection

Bruker Kappa-APEXII diffractometer9335 independent reflections
Radiation source: fine-focus sealed tube8074 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.028
T = 100(2) Kθmax = 36.7º
ω and [var phi] scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Bruker, 2004)h = −13→13
Tmin = 0.507, Tmax = 0.679k = −18→18
44785 measured reflectionsl = −19→19

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.064  w = 1/[σ2(Fo2) + (0.031P)2 + 0.2243P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
9335 reflectionsΔρmax = 0.57 e Å3
237 parametersΔρmin = −0.59 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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

xyzUiso*/Ueq
Se10.135681 (12)0.147694 (9)0.433060 (8)0.01400 (3)
Cl10.22480 (5)0.30162 (4)−0.32615 (2)0.03885 (8)
Cl20.23404 (5)0.83872 (3)0.28700 (3)0.03592 (8)
O10.76068 (10)0.34633 (8)0.28931 (8)0.02212 (15)
O20.67115 (11)0.31526 (8)0.12446 (7)0.02317 (16)
N1−0.02318 (11)0.07149 (8)0.36434 (7)0.01542 (14)
N2−0.01345 (10)0.10161 (8)0.25070 (7)0.01371 (13)
N30.66526 (11)0.30096 (8)0.23302 (8)0.01522 (14)
C10.10681 (11)0.18154 (8)0.20053 (8)0.01114 (14)
C20.20509 (11)0.21946 (8)0.27992 (8)0.01124 (14)
C30.12393 (12)0.21352 (9)0.06915 (8)0.01239 (14)
C40.14006 (15)0.11629 (10)0.00999 (9)0.01870 (18)
H40.13260.03090.05390.022*
C50.16690 (16)0.14320 (11)−0.11262 (9)0.0233 (2)
H50.17710.0771−0.15310.028*
C60.17854 (15)0.26821 (12)−0.17466 (9)0.0219 (2)
C70.15700 (15)0.36712 (10)−0.11909 (9)0.02036 (19)
H70.16120.4526−0.16370.024*
C80.12902 (13)0.33887 (9)0.00348 (8)0.01577 (16)
H80.11320.40580.04290.019*
C90.35407 (11)0.29627 (8)0.24434 (8)0.01096 (13)
H90.36640.30570.15630.013*
C100.32202 (12)0.43177 (9)0.25869 (8)0.01282 (14)
C110.35859 (14)0.53150 (9)0.16337 (9)0.01794 (17)
H110.40160.51330.09140.022*
C120.33342 (17)0.65705 (10)0.17148 (10)0.0229 (2)
H120.35860.72440.10590.027*
C130.27108 (16)0.68213 (10)0.27660 (10)0.0217 (2)
C140.23240 (16)0.58569 (10)0.37302 (10)0.0226 (2)
H140.18950.60450.44480.027*
C150.25739 (15)0.46091 (10)0.36297 (9)0.01862 (18)
H150.22990.39410.42840.022*
C160.52730 (12)0.22146 (9)0.30124 (8)0.01257 (14)
C170.55570 (13)0.09225 (9)0.27148 (10)0.01807 (17)
H17A0.67220.05200.29610.027*
H17B0.54120.10410.18510.027*
H17C0.47190.03770.31420.027*
C180.55381 (13)0.20944 (10)0.43339 (9)0.01800 (17)
H18A0.47040.15690.47950.027*
H18B0.53750.29430.44870.027*
H18C0.67060.16940.45750.027*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Se10.01575 (4)0.01765 (5)0.00888 (4)−0.00696 (3)0.00236 (3)−0.00175 (3)
Cl10.0533 (2)0.0539 (2)0.01020 (10)−0.01394 (17)0.00528 (11)−0.00641 (12)
Cl20.0664 (2)0.01200 (10)0.02912 (14)0.00353 (12)−0.01822 (14)−0.00708 (10)
O10.0197 (3)0.0181 (3)0.0286 (4)−0.0094 (3)−0.0035 (3)−0.0024 (3)
O20.0213 (4)0.0293 (4)0.0161 (3)−0.0055 (3)0.0053 (3)0.0003 (3)
N10.0150 (3)0.0163 (3)0.0150 (3)−0.0058 (3)0.0021 (3)−0.0024 (3)
N20.0135 (3)0.0140 (3)0.0138 (3)−0.0042 (3)0.0012 (2)−0.0027 (3)
N30.0130 (3)0.0131 (3)0.0177 (3)−0.0032 (3)0.0011 (3)0.0003 (3)
C10.0116 (3)0.0109 (3)0.0108 (3)−0.0018 (3)0.0004 (3)−0.0022 (3)
C20.0123 (3)0.0116 (3)0.0095 (3)−0.0024 (3)0.0007 (3)−0.0017 (3)
C30.0143 (4)0.0128 (4)0.0102 (3)−0.0031 (3)−0.0005 (3)−0.0025 (3)
C40.0277 (5)0.0149 (4)0.0149 (4)−0.0051 (4)−0.0010 (3)−0.0050 (3)
C50.0345 (6)0.0236 (5)0.0146 (4)−0.0046 (4)0.0005 (4)−0.0094 (4)
C60.0267 (5)0.0298 (5)0.0097 (4)−0.0075 (4)0.0004 (3)−0.0042 (3)
C70.0276 (5)0.0191 (4)0.0130 (4)−0.0084 (4)−0.0025 (3)0.0010 (3)
C80.0214 (4)0.0132 (4)0.0123 (4)−0.0033 (3)−0.0020 (3)−0.0017 (3)
C90.0124 (3)0.0111 (3)0.0092 (3)−0.0030 (3)0.0004 (3)−0.0016 (3)
C100.0156 (4)0.0110 (3)0.0113 (3)−0.0024 (3)−0.0012 (3)−0.0013 (3)
C110.0264 (5)0.0128 (4)0.0137 (4)−0.0052 (3)0.0011 (3)−0.0006 (3)
C120.0365 (6)0.0120 (4)0.0186 (4)−0.0052 (4)−0.0042 (4)0.0003 (3)
C130.0328 (6)0.0111 (4)0.0212 (5)−0.0001 (4)−0.0095 (4)−0.0044 (3)
C140.0352 (6)0.0155 (4)0.0178 (4)0.0002 (4)−0.0016 (4)−0.0068 (3)
C150.0285 (5)0.0138 (4)0.0134 (4)−0.0028 (4)0.0017 (3)−0.0031 (3)
C160.0122 (3)0.0118 (3)0.0133 (3)−0.0045 (3)0.0007 (3)−0.0011 (3)
C170.0155 (4)0.0130 (4)0.0259 (5)−0.0022 (3)−0.0007 (3)−0.0049 (3)
C180.0172 (4)0.0223 (5)0.0127 (4)−0.0040 (3)−0.0029 (3)−0.0003 (3)

Geometric parameters (Å, °)

Se1—C21.8455 (9)C9—C101.5220 (13)
Se1—N11.8652 (9)C9—C161.5630 (12)
Cl1—C61.7360 (10)C9—H91.0000
Cl2—C131.7350 (10)C10—C111.3918 (13)
O1—N31.2216 (12)C10—C151.3944 (13)
O2—N31.2247 (11)C11—C121.3889 (15)
N1—N21.2734 (11)C11—H110.9500
N2—C11.3795 (12)C12—C131.3802 (16)
N3—C161.5451 (12)C12—H120.9500
C1—C21.3765 (12)C13—C141.3828 (16)
C1—C31.4762 (12)C14—C151.3877 (14)
C2—C91.5075 (13)C14—H140.9500
C3—C81.3923 (13)C15—H150.9500
C3—C41.3938 (13)C16—C181.5144 (13)
C4—C51.3895 (15)C16—C171.5259 (13)
C4—H40.9500C17—H17A0.9800
C5—C61.3851 (17)C17—H17B0.9800
C5—H50.9500C17—H17C0.9800
C6—C71.3826 (16)C18—H18A0.9800
C7—C81.3901 (14)C18—H18B0.9800
C7—H70.9500C18—H18C0.9800
C8—H80.9500
C2—Se1—N187.45 (4)C11—C10—C15118.31 (9)
N2—N1—Se1111.08 (6)C11—C10—C9118.61 (8)
N1—N2—C1117.26 (8)C15—C10—C9123.07 (8)
O1—N3—O2123.86 (9)C12—C11—C10121.26 (10)
O1—N3—C16118.80 (8)C12—C11—H11119.4
O2—N3—C16117.33 (8)C10—C11—H11119.4
C2—C1—N2115.83 (8)C13—C12—C11118.80 (10)
C2—C1—C3126.24 (8)C13—C12—H12120.6
N2—C1—C3117.87 (8)C11—C12—H12120.6
C1—C2—C9124.13 (8)C12—C13—C14121.63 (10)
C1—C2—Se1108.37 (6)C12—C13—Cl2119.39 (9)
C9—C2—Se1127.26 (6)C14—C13—Cl2118.95 (9)
C8—C3—C4119.31 (8)C13—C14—C15118.74 (10)
C8—C3—C1121.17 (8)C13—C14—H14120.6
C4—C3—C1119.50 (8)C15—C14—H14120.6
C5—C4—C3120.54 (10)C14—C15—C10121.25 (10)
C5—C4—H4119.7C14—C15—H15119.4
C3—C4—H4119.7C10—C15—H15119.4
C6—C5—C4118.75 (10)C18—C16—C17111.81 (8)
C6—C5—H5120.6C18—C16—N3107.47 (8)
C4—C5—H5120.6C17—C16—N3106.56 (7)
C7—C6—C5121.93 (9)C18—C16—C9116.40 (8)
C7—C6—Cl1118.93 (9)C17—C16—C9110.03 (7)
C5—C6—Cl1119.13 (9)N3—C16—C9103.77 (7)
C6—C7—C8118.62 (10)C16—C17—H17A109.5
C6—C7—H7120.7C16—C17—H17B109.5
C8—C7—H7120.7H17A—C17—H17B109.5
C7—C8—C3120.74 (9)C16—C17—H17C109.5
C7—C8—H8119.6H17A—C17—H17C109.5
C3—C8—H8119.6H17B—C17—H17C109.5
C2—C9—C10114.26 (7)C16—C18—H18A109.5
C2—C9—C16111.87 (7)C16—C18—H18B109.5
C10—C9—C16114.10 (7)H18A—C18—H18B109.5
C2—C9—H9105.2C16—C18—H18C109.5
C10—C9—H9105.2H18A—C18—H18C109.5
C16—C9—H9105.2H18B—C18—H18C109.5
C2—Se1—N1—N2−0.27 (7)Se1—C2—C9—C1656.27 (10)
Se1—N1—N2—C1−0.06 (10)C2—C9—C10—C11−130.65 (9)
N1—N2—C1—C20.52 (12)C16—C9—C10—C1198.86 (10)
N1—N2—C1—C3177.82 (8)C2—C9—C10—C1549.27 (12)
N2—C1—C2—C9174.02 (8)C16—C9—C10—C15−81.22 (11)
C3—C1—C2—C9−3.01 (14)C15—C10—C11—C120.63 (16)
N2—C1—C2—Se1−0.69 (10)C9—C10—C11—C12−179.44 (10)
C3—C1—C2—Se1−177.72 (7)C10—C11—C12—C130.08 (17)
N1—Se1—C2—C10.52 (7)C11—C12—C13—C14−0.43 (18)
N1—Se1—C2—C9−173.98 (8)C11—C12—C13—Cl2−178.47 (9)
C2—C1—C3—C8−50.52 (14)C12—C13—C14—C150.03 (18)
N2—C1—C3—C8132.50 (10)Cl2—C13—C14—C15178.09 (9)
C2—C1—C3—C4127.69 (11)C13—C14—C15—C100.72 (18)
N2—C1—C3—C4−49.29 (12)C11—C10—C15—C14−1.04 (16)
C8—C3—C4—C52.21 (16)C9—C10—C15—C14179.04 (10)
C1—C3—C4—C5−176.03 (10)O1—N3—C16—C18−4.50 (11)
C3—C4—C5—C60.46 (18)O2—N3—C16—C18175.98 (8)
C4—C5—C6—C7−2.80 (19)O1—N3—C16—C17−124.49 (9)
C4—C5—C6—Cl1176.20 (9)O2—N3—C16—C1755.98 (10)
C5—C6—C7—C82.35 (18)O1—N3—C16—C9119.35 (9)
Cl1—C6—C7—C8−176.64 (9)O2—N3—C16—C9−60.17 (10)
C6—C7—C8—C30.43 (16)C2—C9—C16—C18−74.54 (10)
C4—C3—C8—C7−2.67 (15)C10—C9—C16—C1857.11 (10)
C1—C3—C8—C7175.54 (9)C2—C9—C16—C1753.95 (10)
C1—C2—C9—C10111.01 (10)C10—C9—C16—C17−174.40 (8)
Se1—C2—C9—C10−75.30 (10)C2—C9—C16—N3167.63 (7)
C1—C2—C9—C16−117.41 (9)C10—C9—C16—N3−60.71 (9)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C9—H9···O21.002.422.8271 (12)104
C15—H15···Se10.952.863.5496 (10)130
C18—H18A···Se10.982.703.4209 (10)130
C7—H7···O1i0.952.443.3757 (13)167
C15—H15···Cl1ii0.952.763.5923 (10)147
C17—H17A···N1iii0.982.573.4511 (13)149
C17—H17A···N2iii0.982.603.3919 (13)138

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2267).

References

  • Bertini, V., Dapporto, P., Lucchesini, F., Sega, A. & De Munno, A. (1984). Acta Cryst. C40, 653–655.
  • Bruker (2004). APEX2 (Version 1.0–27) and SADABS (Version 2004/1). Bruker AXS Inc., Madison, Wisconsin, USA.
  • El-Bahaie, S., Assy, M. G. & Hassanien, M. M. (1990). Pharmazie, 45, 791–793. [PubMed]
  • El-Kashef, H. S., E-Bayoumy, B. & Aly, T. I. (1986). Egypt. J. Pharm. Sci.27, 27–30.
  • Gunasekaran, B., Manivannan, V., Saravanan, S., Muthusubramanian, S. & Nethaji, M. (2007). Acta Cryst. E63, o4024.
  • Kuroda, K., Uchikurohane, T., Tajima, S. & Tsubata, K. (2001). US Patent 6 166 054.
  • Mellini, M. & Merlino, S. (1976a). Acta Cryst. B32, 1074–1078.
  • Mellini, M. & Merlino, S. (1976b). Acta Cryst. B32, 1079–1082.
  • Padmavathi, V., Sumathi, R. P. & Padmaja, A. (2002). J. Ecobiol.14, 9–12.
  • Saravanan, S., Nithya, A. & Muthusubramanian, S. (2006). J. Heterocycl. Chem.43, 149–151.
  • Sheldrick, G. M. (1997). SHELXL97 and SHELXS97 University of Göttingen, Germany.
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography