Literature DB >> 22412724

5-(2-Nitro-1-phenyl-but-yl)-4-phenyl-1,2,3-selenadiazole.

S Sankari, P Sugumar, P Manisankar, S Muthusubramanian, M N Ponnuswamy.   

Abstract

In the title compound, C(18)H(17)N(3)O(2)Se, the selenadiazole ring is planar [maximum deviation = 0.012 (2) Å for the ring C atom bearing the phenyl substituent]. The dihedral angle between the selenadiazole ring and the attached benzene ring is 46.5 (1)°. There is one short intra-molecular C-H⋯Se contact.

Entities:  

Year:  2012        PMID： 22412724      PMCID： PMC3297921          DOI： 10.1107/S1600536812007027

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For general background to selenadiazole derivatives, see: El-Bahaie et al. (1990 ▶); El-Kashef et al. (1986 ▶); Kuroda et al. (2001 ▶); Khanna (2005 ▶); Padmavathi et al. (2002 ▶); Plano et al. (2010 ▶); Stadtman (1991 ▶).

Experimental

Crystal data

C18H17N3O2Se M = 386.31 Triclinic, a = 7.879 (5) Å b = 8.450 (5) Å c = 13.438 (5) Å α = 80.629 (5)° β = 85.273 (5)° γ = 75.352 (5)° V = 853.2 (8) Å3 Z = 2 Mo Kα radiation μ = 2.22 mm−1 T = 293 K 0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.636, T max = 0.702 15132 measured reflections 4265 independent reflections 3478 reflections with I > 2σ(I) R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.032 wR(F 2) = 0.079 S = 1.05 4265 reflections 218 parameters H-atom parameters constrained Δρmax = 0.43 e Å−3 Δρmin = −0.21 e Å−3 Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812007027/bt5784sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007027/bt5784Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812007027/bt5784Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H17N3O2SeZ = 2
Mr = 386.31F(000) = 392
Triclinic, P1Dx = 1.504 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.879 (5) ÅCell parameters from 3478 reflections
b = 8.450 (5) Åθ = 1.5–28.4°
c = 13.438 (5) ŵ = 2.22 mm−1
α = 80.629 (5)°T = 293 K
β = 85.273 (5)°Block, white crystalline
γ = 75.352 (5)°0.20 × 0.18 × 0.16 mm
V = 853.2 (8) Å3
Bruker SMART APEX CCD detector diffractometer4265 independent reflections
Radiation source: fine-focus sealed tube3478 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω scansθmax = 28.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −10→10
Tmin = 0.636, Tmax = 0.702k = −11→11
15132 measured reflectionsl = −17→17
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0382P)2 + 0.1656P] where P = (Fo2 + 2Fc2)/3
4265 reflections(Δ/σ)max = 0.001
218 parametersΔρmax = 0.43 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
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.
xyzUiso*/Ueq
C10.7979 (3)0.3866 (2)0.50318 (16)0.0513 (5)
H10.85900.46850.48490.062*
C20.6659 (3)0.4053 (3)0.57649 (18)0.0634 (6)
H20.63910.49910.60820.076*
C30.5726 (3)0.2865 (3)0.60360 (17)0.0621 (6)
H30.48220.30050.65290.074*
C40.6131 (3)0.1475 (3)0.55777 (15)0.0535 (5)
H40.55000.06710.57600.064*
C50.7476 (3)0.1260 (2)0.48458 (14)0.0472 (4)
H50.77540.03050.45450.057*
C60.8415 (2)0.2461 (2)0.45570 (13)0.0405 (4)
C70.9868 (2)0.2266 (2)0.37864 (13)0.0402 (4)
C80.9887 (2)0.1804 (2)0.28553 (13)0.0386 (4)
C90.8345 (2)0.1554 (2)0.23419 (12)0.0375 (4)
H90.74440.13900.28690.045*
C100.7575 (2)0.3138 (2)0.16406 (13)0.0374 (4)
C110.6121 (2)0.4253 (3)0.19758 (15)0.0504 (5)
H110.55770.39860.26000.060*
C120.5464 (3)0.5762 (3)0.13925 (18)0.0604 (6)
H120.44950.65070.16320.073*
C130.6231 (3)0.6164 (3)0.04674 (18)0.0574 (5)
H130.57900.71810.00780.069*
C140.7656 (3)0.5060 (3)0.01180 (16)0.0542 (5)
H140.81700.5324−0.05150.065*
C150.8332 (2)0.3560 (2)0.06965 (14)0.0467 (4)
H150.93040.28240.04520.056*
C160.8902 (2)−0.0021 (2)0.18459 (14)0.0413 (4)
H160.99430.00270.14010.050*
C170.9315 (3)−0.1575 (2)0.26163 (16)0.0581 (5)
H17A0.8273−0.16240.30470.070*
H17B1.0224−0.15000.30390.070*
C180.9917 (4)−0.3167 (3)0.2162 (2)0.0771 (7)
H18A0.8991−0.32990.17860.116*
H18B1.0210−0.40870.26930.116*
H18C1.0932−0.31230.17210.116*
N11.2673 (2)0.2439 (2)0.33702 (14)0.0551 (4)
N21.1401 (2)0.26173 (19)0.40163 (13)0.0496 (4)
N30.7421 (2)−0.0094 (2)0.12234 (14)0.0520 (4)
O10.6009 (2)−0.0054 (2)0.16418 (16)0.0848 (6)
O20.7744 (3)−0.0209 (2)0.03327 (13)0.0806 (5)
Se11.20608 (2)0.17348 (3)0.222464 (15)0.05307 (9)
U11U22U33U12U13U23
C10.0508 (11)0.0522 (11)0.0580 (12)−0.0167 (9)−0.0044 (9)−0.0211 (9)
C20.0607 (13)0.0703 (14)0.0679 (14)−0.0155 (11)0.0054 (11)−0.0404 (12)
C30.0570 (12)0.0811 (15)0.0517 (12)−0.0177 (11)0.0088 (10)−0.0242 (11)
C40.0616 (12)0.0603 (12)0.0428 (10)−0.0248 (10)0.0020 (9)−0.0059 (9)
C50.0632 (12)0.0442 (10)0.0373 (9)−0.0175 (9)0.0000 (8)−0.0091 (8)
C60.0462 (9)0.0418 (9)0.0350 (9)−0.0104 (7)−0.0070 (7)−0.0076 (7)
C70.0453 (9)0.0353 (9)0.0416 (9)−0.0128 (7)−0.0064 (7)−0.0038 (7)
C80.0398 (9)0.0380 (9)0.0380 (9)−0.0112 (7)−0.0009 (7)−0.0034 (7)
C90.0377 (8)0.0442 (9)0.0322 (8)−0.0120 (7)0.0031 (7)−0.0093 (7)
C100.0355 (8)0.0433 (9)0.0364 (9)−0.0119 (7)−0.0018 (7)−0.0109 (7)
C110.0442 (10)0.0607 (12)0.0448 (10)−0.0055 (9)0.0026 (8)−0.0173 (9)
C120.0505 (11)0.0570 (12)0.0685 (14)0.0073 (9)−0.0104 (10)−0.0224 (11)
C130.0622 (13)0.0466 (11)0.0648 (14)−0.0111 (10)−0.0239 (11)−0.0051 (10)
C140.0574 (12)0.0578 (12)0.0477 (11)−0.0199 (10)−0.0058 (9)0.0027 (9)
C150.0431 (10)0.0503 (10)0.0438 (10)−0.0077 (8)0.0043 (8)−0.0079 (8)
C160.0371 (9)0.0457 (9)0.0434 (10)−0.0104 (7)−0.0020 (7)−0.0124 (8)
C170.0701 (14)0.0475 (11)0.0566 (12)−0.0120 (10)−0.0104 (11)−0.0076 (9)
C180.0883 (18)0.0497 (12)0.0921 (19)−0.0035 (12)−0.0234 (15)−0.0188 (12)
N10.0489 (9)0.0578 (10)0.0633 (11)−0.0226 (8)−0.0079 (8)−0.0049 (8)
N20.0519 (9)0.0463 (9)0.0558 (10)−0.0185 (7)−0.0095 (8)−0.0084 (7)
N30.0475 (9)0.0498 (9)0.0628 (11)−0.0097 (7)−0.0080 (8)−0.0208 (8)
O10.0418 (8)0.1059 (14)0.1195 (16)−0.0223 (9)0.0029 (9)−0.0505 (12)
O20.0947 (13)0.1034 (13)0.0561 (10)−0.0334 (11)−0.0161 (9)−0.0264 (9)
Se10.04099 (12)0.07035 (15)0.04790 (13)−0.01791 (9)0.00333 (8)−0.00448 (9)
C1—C21.370 (3)C11—H110.9300
C1—C61.392 (3)C12—C131.367 (3)
C1—H10.9300C12—H120.9300
C2—C31.375 (3)C13—C141.370 (3)
C2—H20.9300C13—H130.9300
C3—C41.369 (3)C14—C151.379 (3)
C3—H30.9300C14—H140.9300
C4—C51.383 (3)C15—H150.9300
C4—H40.9300C16—N31.510 (2)
C5—C61.390 (3)C16—C171.516 (3)
C5—H50.9300C16—H160.9800
C6—C71.475 (3)C17—C181.518 (3)
C7—C81.368 (3)C17—H17A0.9700
C7—N21.384 (2)C17—H17B0.9700
C8—C91.520 (2)C18—H18A0.9600
C8—Se11.839 (2)C18—H18B0.9600
C9—C101.523 (2)C18—H18C0.9600
C9—C161.534 (3)N1—N21.267 (2)
C9—H90.9800N1—Se11.8770 (19)
C10—C111.382 (3)N3—O11.200 (2)
C10—C151.388 (3)N3—O21.217 (2)
C11—C121.384 (3)
C2—C1—C6120.63 (19)C13—C12—C11120.4 (2)
C2—C1—H1119.7C13—C12—H12119.8
C6—C1—H1119.7C11—C12—H12119.8
C1—C2—C3120.5 (2)C12—C13—C14119.5 (2)
C1—C2—H2119.7C12—C13—H13120.2
C3—C2—H2119.7C14—C13—H13120.2
C4—C3—C2119.8 (2)C13—C14—C15120.6 (2)
C4—C3—H3120.1C13—C14—H14119.7
C2—C3—H3120.1C15—C14—H14119.7
C3—C4—C5120.29 (19)C14—C15—C10120.59 (18)
C3—C4—H4119.9C14—C15—H15119.7
C5—C4—H4119.9C10—C15—H15119.7
C4—C5—C6120.47 (18)N3—C16—C17108.74 (15)
C4—C5—H5119.8N3—C16—C9108.55 (14)
C6—C5—H5119.8C17—C16—C9112.31 (16)
C5—C6—C1118.29 (18)N3—C16—H16109.1
C5—C6—C7121.95 (16)C17—C16—H16109.1
C1—C6—C7119.75 (16)C9—C16—H16109.1
C8—C7—N2115.23 (17)C16—C17—C18114.36 (19)
C8—C7—C6128.04 (16)C16—C17—H17A108.7
N2—C7—C6116.72 (16)C18—C17—H17A108.7
C7—C8—C9127.23 (16)C16—C17—H17B108.7
C7—C8—Se1109.19 (12)C18—C17—H17B108.7
C9—C8—Se1123.28 (13)H17A—C17—H17B107.6
C8—C9—C10108.57 (14)C17—C18—H18A109.5
C8—C9—C16110.27 (14)C17—C18—H18B109.5
C10—C9—C16115.55 (14)H18A—C18—H18B109.5
C8—C9—H9107.4C17—C18—H18C109.5
C10—C9—H9107.4H18A—C18—H18C109.5
C16—C9—H9107.4H18B—C18—H18C109.5
C11—C10—C15118.18 (17)N2—N1—Se1110.66 (13)
C11—C10—C9118.95 (16)N1—N2—C7117.79 (17)
C15—C10—C9122.76 (16)O1—N3—O2124.35 (19)
C10—C11—C12120.69 (19)O1—N3—C16117.82 (18)
C10—C11—H11119.7O2—N3—C16117.82 (18)
C12—C11—H11119.7C8—Se1—N187.09 (8)
C6—C1—C2—C3−0.8 (3)C15—C10—C11—C12−1.4 (3)
C1—C2—C3—C40.7 (4)C9—C10—C11—C12174.97 (17)
C2—C3—C4—C50.1 (3)C10—C11—C12—C130.9 (3)
C3—C4—C5—C6−0.9 (3)C11—C12—C13—C140.2 (3)
C4—C5—C6—C10.8 (3)C12—C13—C14—C15−0.9 (3)
C4—C5—C6—C7179.39 (17)C13—C14—C15—C100.4 (3)
C2—C1—C6—C50.1 (3)C11—C10—C15—C140.7 (3)
C2—C1—C6—C7−178.58 (19)C9—C10—C15—C14−175.49 (17)
C5—C6—C7—C848.1 (3)C8—C9—C16—N3−172.07 (14)
C1—C6—C7—C8−133.27 (19)C10—C9—C16—N3−48.5 (2)
C5—C6—C7—N2−133.04 (18)C8—C9—C16—C1767.67 (19)
C1—C6—C7—N245.6 (2)C10—C9—C16—C17−168.76 (16)
N2—C7—C8—C9−171.71 (16)N3—C16—C17—C1861.3 (2)
C6—C7—C8—C97.1 (3)C9—C16—C17—C18−178.51 (18)
N2—C7—C8—Se12.08 (19)Se1—N1—N2—C70.6 (2)
C6—C7—C8—Se1−179.08 (14)C8—C7—N2—N1−1.9 (2)
C7—C8—C9—C1095.8 (2)C6—C7—N2—N1179.17 (16)
Se1—C8—C9—C10−77.17 (17)C17—C16—N3—O165.7 (2)
C7—C8—C9—C16−136.66 (18)C9—C16—N3—O1−56.7 (2)
Se1—C8—C9—C1650.36 (19)C17—C16—N3—O2−113.5 (2)
C8—C9—C10—C11−97.56 (19)C9—C16—N3—O2124.09 (18)
C16—C9—C10—C11137.99 (17)C7—C8—Se1—N1−1.40 (12)
C8—C9—C10—C1578.6 (2)C9—C8—Se1—N1172.68 (15)
C16—C9—C10—C15−45.8 (2)N2—N1—Se1—C80.48 (14)
D—H···AD—HH···AD···AD—H···A
C16—H16···Se10.982.853.313 (3)110
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C16—H16⋯Se10.982.853.313 (3)110
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