Acta Cryst. (2008). E64, o349 [ doi:10.1107/S1600536807067487 ]
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-HSe interactions and intermolecular C-HO, C-HCl and C-HN interactions are observed.
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.
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.
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
![[Figure 1]](./is2267fig1thm.gif)
| Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms. |
![[Figure 2]](./is2267fig2thm.gif)
| 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. |
| C18H15Cl2N3O2Se | Z = 2 |
| Mr = 455.19 | F000 = 456 |
| Triclinic, P1 | Dx = 1.592 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 7.8352 (2) Å | Cell parameters from 8302 reflections |
| b = 10.9208 (3) Å | θ = 2.7–34.5º |
| c = 11.5507 (3) Å | µ = 2.28 mm−1 |
| α = 75.381 (1)º | T = 100 (2) K |
| β = 89.044 (1)º | Rectangular, colourless |
| γ = 83.331 (1)º | 0.33 × 0.18 × 0.17 mm |
| V = 949.80 (4) Å3 |
| Bruker Kappa-APEXII diffractometer | 9335 independent reflections |
| Radiation source: fine-focus sealed tube | 8074 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.028 |
| T = 100(2) K | θmax = 36.7º |
| ω and φ scans | θmin = 1.8º |
| Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −13→13 |
| Tmin = 0.507, Tmax = 0.679 | k = −18→18 |
| 44785 measured reflections | l = −19→19 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.026 | H-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 reflections | Δρmax = 0.57 e Å−3 |
| 237 parameters | Δρmin = −0.59 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C18H15Cl2N3O2Se | γ = 83.331 (1)º |
| Mr = 455.19 | V = 949.80 (4) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 7.8352 (2) Å | Mo Kα |
| b = 10.9208 (3) Å | µ = 2.28 mm−1 |
| c = 11.5507 (3) Å | T = 100 (2) K |
| α = 75.381 (1)º | 0.33 × 0.18 × 0.17 mm |
| β = 89.044 (1)º |
| Bruker Kappa-APEXII diffractometer | 9335 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2004) | 8074 reflections with I > 2σ(I) |
| Tmin = 0.507, Tmax = 0.679 | Rint = 0.028 |
| 44785 measured reflections |
| R[F2 > 2σ(F2)] = 0.026 | 237 parameters |
| wR(F2) = 0.064 | H-atom parameters constrained |
| S = 1.03 | Δρmax = 0.57 e Å−3 |
| 9335 reflections | Δρmin = −0.59 e Å−3 |
| x | y | z | Uiso*/Ueq | ||
| Se1 | 0.135681 (12) | 0.147694 (9) | 0.433060 (8) | 0.01400 (3) | |
| Cl1 | 0.22480 (5) | 0.30162 (4) | −0.32615 (2) | 0.03885 (8) | |
| Cl2 | 0.23404 (5) | 0.83872 (3) | 0.28700 (3) | 0.03592 (8) | |
| O1 | 0.76068 (10) | 0.34633 (8) | 0.28931 (8) | 0.02212 (15) | |
| O2 | 0.67115 (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) | |
| N3 | 0.66526 (11) | 0.30096 (8) | 0.23302 (8) | 0.01522 (14) | |
| C1 | 0.10681 (11) | 0.18154 (8) | 0.20053 (8) | 0.01114 (14) | |
| C2 | 0.20509 (11) | 0.21946 (8) | 0.27992 (8) | 0.01124 (14) | |
| C3 | 0.12393 (12) | 0.21352 (9) | 0.06915 (8) | 0.01239 (14) | |
| C4 | 0.14006 (15) | 0.11629 (10) | 0.00999 (9) | 0.01870 (18) | |
| H4 | 0.1326 | 0.0309 | 0.0539 | 0.022* | |
| C5 | 0.16690 (16) | 0.14320 (11) | −0.11262 (9) | 0.0233 (2) | |
| H5 | 0.1771 | 0.0771 | −0.1531 | 0.028* | |
| C6 | 0.17854 (15) | 0.26821 (12) | −0.17466 (9) | 0.0219 (2) | |
| C7 | 0.15700 (15) | 0.36712 (10) | −0.11909 (9) | 0.02036 (19) | |
| H7 | 0.1612 | 0.4526 | −0.1637 | 0.024* | |
| C8 | 0.12902 (13) | 0.33887 (9) | 0.00348 (8) | 0.01577 (16) | |
| H8 | 0.1132 | 0.4058 | 0.0429 | 0.019* | |
| C9 | 0.35407 (11) | 0.29627 (8) | 0.24434 (8) | 0.01096 (13) | |
| H9 | 0.3664 | 0.3057 | 0.1563 | 0.013* | |
| C10 | 0.32202 (12) | 0.43177 (9) | 0.25869 (8) | 0.01282 (14) | |
| C11 | 0.35859 (14) | 0.53150 (9) | 0.16337 (9) | 0.01794 (17) | |
| H11 | 0.4016 | 0.5133 | 0.0914 | 0.022* | |
| C12 | 0.33342 (17) | 0.65705 (10) | 0.17148 (10) | 0.0229 (2) | |
| H12 | 0.3586 | 0.7244 | 0.1059 | 0.027* | |
| C13 | 0.27108 (16) | 0.68213 (10) | 0.27660 (10) | 0.0217 (2) | |
| C14 | 0.23240 (16) | 0.58569 (10) | 0.37302 (10) | 0.0226 (2) | |
| H14 | 0.1895 | 0.6045 | 0.4448 | 0.027* | |
| C15 | 0.25739 (15) | 0.46091 (10) | 0.36297 (9) | 0.01862 (18) | |
| H15 | 0.2299 | 0.3941 | 0.4284 | 0.022* | |
| C16 | 0.52730 (12) | 0.22146 (9) | 0.30124 (8) | 0.01257 (14) | |
| C17 | 0.55570 (13) | 0.09225 (9) | 0.27148 (10) | 0.01807 (17) | |
| H17A | 0.6722 | 0.0520 | 0.2961 | 0.027* | |
| H17B | 0.5412 | 0.1041 | 0.1851 | 0.027* | |
| H17C | 0.4719 | 0.0377 | 0.3142 | 0.027* | |
| C18 | 0.55381 (13) | 0.20944 (10) | 0.43339 (9) | 0.01800 (17) | |
| H18A | 0.4704 | 0.1569 | 0.4795 | 0.027* | |
| H18B | 0.5375 | 0.2943 | 0.4487 | 0.027* | |
| H18C | 0.6706 | 0.1694 | 0.4575 | 0.027* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Se1 | 0.01575 (4) | 0.01765 (5) | 0.00888 (4) | −0.00696 (3) | 0.00236 (3) | −0.00175 (3) |
| Cl1 | 0.0533 (2) | 0.0539 (2) | 0.01020 (10) | −0.01394 (17) | 0.00528 (11) | −0.00641 (12) |
| Cl2 | 0.0664 (2) | 0.01200 (10) | 0.02912 (14) | 0.00353 (12) | −0.01822 (14) | −0.00708 (10) |
| O1 | 0.0197 (3) | 0.0181 (3) | 0.0286 (4) | −0.0094 (3) | −0.0035 (3) | −0.0024 (3) |
| O2 | 0.0213 (4) | 0.0293 (4) | 0.0161 (3) | −0.0055 (3) | 0.0053 (3) | 0.0003 (3) |
| N1 | 0.0150 (3) | 0.0163 (3) | 0.0150 (3) | −0.0058 (3) | 0.0021 (3) | −0.0024 (3) |
| N2 | 0.0135 (3) | 0.0140 (3) | 0.0138 (3) | −0.0042 (3) | 0.0012 (2) | −0.0027 (3) |
| N3 | 0.0130 (3) | 0.0131 (3) | 0.0177 (3) | −0.0032 (3) | 0.0011 (3) | 0.0003 (3) |
| C1 | 0.0116 (3) | 0.0109 (3) | 0.0108 (3) | −0.0018 (3) | 0.0004 (3) | −0.0022 (3) |
| C2 | 0.0123 (3) | 0.0116 (3) | 0.0095 (3) | −0.0024 (3) | 0.0007 (3) | −0.0017 (3) |
| C3 | 0.0143 (4) | 0.0128 (4) | 0.0102 (3) | −0.0031 (3) | −0.0005 (3) | −0.0025 (3) |
| C4 | 0.0277 (5) | 0.0149 (4) | 0.0149 (4) | −0.0051 (4) | −0.0010 (3) | −0.0050 (3) |
| C5 | 0.0345 (6) | 0.0236 (5) | 0.0146 (4) | −0.0046 (4) | 0.0005 (4) | −0.0094 (4) |
| C6 | 0.0267 (5) | 0.0298 (5) | 0.0097 (4) | −0.0075 (4) | 0.0004 (3) | −0.0042 (3) |
| C7 | 0.0276 (5) | 0.0191 (4) | 0.0130 (4) | −0.0084 (4) | −0.0025 (3) | 0.0010 (3) |
| C8 | 0.0214 (4) | 0.0132 (4) | 0.0123 (4) | −0.0033 (3) | −0.0020 (3) | −0.0017 (3) |
| C9 | 0.0124 (3) | 0.0111 (3) | 0.0092 (3) | −0.0030 (3) | 0.0004 (3) | −0.0016 (3) |
| C10 | 0.0156 (4) | 0.0110 (3) | 0.0113 (3) | −0.0024 (3) | −0.0012 (3) | −0.0013 (3) |
| C11 | 0.0264 (5) | 0.0128 (4) | 0.0137 (4) | −0.0052 (3) | 0.0011 (3) | −0.0006 (3) |
| C12 | 0.0365 (6) | 0.0120 (4) | 0.0186 (4) | −0.0052 (4) | −0.0042 (4) | 0.0003 (3) |
| C13 | 0.0328 (6) | 0.0111 (4) | 0.0212 (5) | −0.0001 (4) | −0.0095 (4) | −0.0044 (3) |
| C14 | 0.0352 (6) | 0.0155 (4) | 0.0178 (4) | 0.0002 (4) | −0.0016 (4) | −0.0068 (3) |
| C15 | 0.0285 (5) | 0.0138 (4) | 0.0134 (4) | −0.0028 (4) | 0.0017 (3) | −0.0031 (3) |
| C16 | 0.0122 (3) | 0.0118 (3) | 0.0133 (3) | −0.0045 (3) | 0.0007 (3) | −0.0011 (3) |
| C17 | 0.0155 (4) | 0.0130 (4) | 0.0259 (5) | −0.0022 (3) | −0.0007 (3) | −0.0049 (3) |
| C18 | 0.0172 (4) | 0.0223 (5) | 0.0127 (4) | −0.0040 (3) | −0.0029 (3) | −0.0003 (3) |
| Se1—C2 | 1.8455 (9) | C9—C10 | 1.5220 (13) |
| Se1—N1 | 1.8652 (9) | C9—C16 | 1.5630 (12) |
| Cl1—C6 | 1.7360 (10) | C9—H9 | 1.0000 |
| Cl2—C13 | 1.7350 (10) | C10—C11 | 1.3918 (13) |
| O1—N3 | 1.2216 (12) | C10—C15 | 1.3944 (13) |
| O2—N3 | 1.2247 (11) | C11—C12 | 1.3889 (15) |
| N1—N2 | 1.2734 (11) | C11—H11 | 0.9500 |
| N2—C1 | 1.3795 (12) | C12—C13 | 1.3802 (16) |
| N3—C16 | 1.5451 (12) | C12—H12 | 0.9500 |
| C1—C2 | 1.3765 (12) | C13—C14 | 1.3828 (16) |
| C1—C3 | 1.4762 (12) | C14—C15 | 1.3877 (14) |
| C2—C9 | 1.5075 (13) | C14—H14 | 0.9500 |
| C3—C8 | 1.3923 (13) | C15—H15 | 0.9500 |
| C3—C4 | 1.3938 (13) | C16—C18 | 1.5144 (13) |
| C4—C5 | 1.3895 (15) | C16—C17 | 1.5259 (13) |
| C4—H4 | 0.9500 | C17—H17A | 0.9800 |
| C5—C6 | 1.3851 (17) | C17—H17B | 0.9800 |
| C5—H5 | 0.9500 | C17—H17C | 0.9800 |
| C6—C7 | 1.3826 (16) | C18—H18A | 0.9800 |
| C7—C8 | 1.3901 (14) | C18—H18B | 0.9800 |
| C7—H7 | 0.9500 | C18—H18C | 0.9800 |
| C8—H8 | 0.9500 | ||
| C2—Se1—N1 | 87.45 (4) | C11—C10—C15 | 118.31 (9) |
| N2—N1—Se1 | 111.08 (6) | C11—C10—C9 | 118.61 (8) |
| N1—N2—C1 | 117.26 (8) | C15—C10—C9 | 123.07 (8) |
| O1—N3—O2 | 123.86 (9) | C12—C11—C10 | 121.26 (10) |
| O1—N3—C16 | 118.80 (8) | C12—C11—H11 | 119.4 |
| O2—N3—C16 | 117.33 (8) | C10—C11—H11 | 119.4 |
| C2—C1—N2 | 115.83 (8) | C13—C12—C11 | 118.80 (10) |
| C2—C1—C3 | 126.24 (8) | C13—C12—H12 | 120.6 |
| N2—C1—C3 | 117.87 (8) | C11—C12—H12 | 120.6 |
| C1—C2—C9 | 124.13 (8) | C12—C13—C14 | 121.63 (10) |
| C1—C2—Se1 | 108.37 (6) | C12—C13—Cl2 | 119.39 (9) |
| C9—C2—Se1 | 127.26 (6) | C14—C13—Cl2 | 118.95 (9) |
| C8—C3—C4 | 119.31 (8) | C13—C14—C15 | 118.74 (10) |
| C8—C3—C1 | 121.17 (8) | C13—C14—H14 | 120.6 |
| C4—C3—C1 | 119.50 (8) | C15—C14—H14 | 120.6 |
| C5—C4—C3 | 120.54 (10) | C14—C15—C10 | 121.25 (10) |
| C5—C4—H4 | 119.7 | C14—C15—H15 | 119.4 |
| C3—C4—H4 | 119.7 | C10—C15—H15 | 119.4 |
| C6—C5—C4 | 118.75 (10) | C18—C16—C17 | 111.81 (8) |
| C6—C5—H5 | 120.6 | C18—C16—N3 | 107.47 (8) |
| C4—C5—H5 | 120.6 | C17—C16—N3 | 106.56 (7) |
| C7—C6—C5 | 121.93 (9) | C18—C16—C9 | 116.40 (8) |
| C7—C6—Cl1 | 118.93 (9) | C17—C16—C9 | 110.03 (7) |
| C5—C6—Cl1 | 119.13 (9) | N3—C16—C9 | 103.77 (7) |
| C6—C7—C8 | 118.62 (10) | C16—C17—H17A | 109.5 |
| C6—C7—H7 | 120.7 | C16—C17—H17B | 109.5 |
| C8—C7—H7 | 120.7 | H17A—C17—H17B | 109.5 |
| C7—C8—C3 | 120.74 (9) | C16—C17—H17C | 109.5 |
| C7—C8—H8 | 119.6 | H17A—C17—H17C | 109.5 |
| C3—C8—H8 | 119.6 | H17B—C17—H17C | 109.5 |
| C2—C9—C10 | 114.26 (7) | C16—C18—H18A | 109.5 |
| C2—C9—C16 | 111.87 (7) | C16—C18—H18B | 109.5 |
| C10—C9—C16 | 114.10 (7) | H18A—C18—H18B | 109.5 |
| C2—C9—H9 | 105.2 | C16—C18—H18C | 109.5 |
| C10—C9—H9 | 105.2 | H18A—C18—H18C | 109.5 |
| C16—C9—H9 | 105.2 | H18B—C18—H18C | 109.5 |
| C2—Se1—N1—N2 | −0.27 (7) | Se1—C2—C9—C16 | 56.27 (10) |
| Se1—N1—N2—C1 | −0.06 (10) | C2—C9—C10—C11 | −130.65 (9) |
| N1—N2—C1—C2 | 0.52 (12) | C16—C9—C10—C11 | 98.86 (10) |
| N1—N2—C1—C3 | 177.82 (8) | C2—C9—C10—C15 | 49.27 (12) |
| N2—C1—C2—C9 | 174.02 (8) | C16—C9—C10—C15 | −81.22 (11) |
| C3—C1—C2—C9 | −3.01 (14) | C15—C10—C11—C12 | 0.63 (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—C13 | 0.08 (17) |
| N1—Se1—C2—C1 | 0.52 (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—C15 | 0.03 (18) |
| N2—C1—C3—C8 | 132.50 (10) | Cl2—C13—C14—C15 | 178.09 (9) |
| C2—C1—C3—C4 | 127.69 (11) | C13—C14—C15—C10 | 0.72 (18) |
| N2—C1—C3—C4 | −49.29 (12) | C11—C10—C15—C14 | −1.04 (16) |
| C8—C3—C4—C5 | 2.21 (16) | C9—C10—C15—C14 | 179.04 (10) |
| C1—C3—C4—C5 | −176.03 (10) | O1—N3—C16—C18 | −4.50 (11) |
| C3—C4—C5—C6 | 0.46 (18) | O2—N3—C16—C18 | 175.98 (8) |
| C4—C5—C6—C7 | −2.80 (19) | O1—N3—C16—C17 | −124.49 (9) |
| C4—C5—C6—Cl1 | 176.20 (9) | O2—N3—C16—C17 | 55.98 (10) |
| C5—C6—C7—C8 | 2.35 (18) | O1—N3—C16—C9 | 119.35 (9) |
| Cl1—C6—C7—C8 | −176.64 (9) | O2—N3—C16—C9 | −60.17 (10) |
| C6—C7—C8—C3 | 0.43 (16) | C2—C9—C16—C18 | −74.54 (10) |
| C4—C3—C8—C7 | −2.67 (15) | C10—C9—C16—C18 | 57.11 (10) |
| C1—C3—C8—C7 | 175.54 (9) | C2—C9—C16—C17 | 53.95 (10) |
| C1—C2—C9—C10 | 111.01 (10) | C10—C9—C16—C17 | −174.40 (8) |
| Se1—C2—C9—C10 | −75.30 (10) | C2—C9—C16—N3 | 167.63 (7) |
| C1—C2—C9—C16 | −117.41 (9) | C10—C9—C16—N3 | −60.71 (9) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C9—H9···O2 | 1.00 | 2.42 | 2.8271 (12) | 104 |
| C15—H15···Se1 | 0.95 | 2.86 | 3.5496 (10) | 130 |
| C18—H18A···Se1 | 0.98 | 2.70 | 3.4209 (10) | 130 |
| C7—H7···O1i | 0.95 | 2.44 | 3.3757 (13) | 167 |
| C15—H15···Cl1ii | 0.95 | 2.76 | 3.5923 (10) | 147 |
| C17—H17A···N1iii | 0.98 | 2.57 | 3.4511 (13) | 149 |
| C17—H17A···N2iii | 0.98 | 2.60 | 3.3919 (13) | 138 |
| Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y, z+1; (iii) x+1, y, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C9—H9···O2 | 1.00 | 2.42 | 2.8271 (12) | 104 |
| C15—H15···Se1 | 0.95 | 2.86 | 3.5496 (10) | 130 |
| C18—H18A···Se1 | 0.98 | 2.70 | 3.4209 (10) | 130 |
| C7—H7···O1i | 0.95 | 2.44 | 3.3757 (13) | 167 |
| C15—H15···Cl1ii | 0.95 | 2.76 | 3.5923 (10) | 147 |
| C17—H17A···N1iii | 0.98 | 2.57 | 3.4511 (13) | 149 |
| C17—H17A···N2iii | 0.98 | 2.60 | 3.3919 (13) | 138 |
| Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y, z+1; (iii) x+1, y, z. |
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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).