Literature DB >> 22091044

1-(2-Naphth-yl)-3-phenyl-3-(4,5,6,7-tetra-hydro-1,2,3-benzoselenadiazol-4-yl)propan-1-one.

J Muthukumaran, M Nachiappan, S Chitra, P Manisankar, Suman Bhattacharya, S Muthusubramanian, R Krishna, J Jeyakanthan.   

Abstract

In the title compound, C(25)H(22)N(2)OSe, the fused six-membered cyclo-hexene ring of the 4,5,6,7-tetra-hydro-1,2,3-benzoselenadiazole group adopts a near half-chair conformation and the five-membered 1,2,3-selenadiazole ring is essentially planar (r.m.s. deviation = 0.004 Å). There are weak inter-molecular C-H⋯O and C-H⋯π inter-actions in the crystal structure. Inter-molecular π-π stacking is also observed between the naphthyl units, with a centroid-centroid distance of 3.529 (15) Å.

Entities:  

Year:  2011        PMID： 22091044      PMCID： PMC3213465          DOI： 10.1107/S1600536811027103

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


Related literature

For the biological importance 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 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶). For synthetic procedures, see: Al Arab (1989 ▶); Li et al. (2003 ▶); Qian et al. (2008 ▶); Xu et al. (2009 ▶).

Experimental

Crystal data

C25H22N2OSe M = 445.41 Triclinic, a = 8.0600 (4) Å b = 10.1215 (5) Å c = 13.0827 (6) Å α = 81.479 (4)° β = 76.478 (4)° γ = 82.087 (4)° V = 1020.33 (9) Å3 Z = 2 Mo Kα radiation μ = 1.86 mm−1 T = 293 K 0.4 × 0.3 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.658, T max = 1.000 6762 measured reflections 3594 independent reflections 2770 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.096 S = 1.01 3594 reflections 262 parameters H-atom parameters constrained Δρmax = 0.29 e Å−3 Δρmin = −0.41 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811027103/gk2375sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027103/gk2375Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811027103/gk2375Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C25H22N2OSeZ = 2
Mr = 445.41F(000) = 456
Triclinic, P1Dx = 1.450 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0600 (4) ÅCell parameters from 3065 reflections
b = 10.1215 (5) Åθ = 2.6–29.3°
c = 13.0827 (6) ŵ = 1.86 mm−1
α = 81.479 (4)°T = 293 K
β = 76.478 (4)°Block, blue
γ = 82.087 (4)°0.4 × 0.3 × 0.2 mm
V = 1020.33 (9) Å3
Oxford Diffraction Xcalibur E diffractometer3594 independent reflections
Radiation source: fine-focus sealed tube2770 reflections with I > 2σ(I)
graphiteRint = 0.025
Detector resolution: 15.9821 pixels mm-1θmax = 25.0°, θmin = 2.6°
ω scansh = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)k = −12→12
Tmin = 0.658, Tmax = 1.000l = −12→15
6762 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.050P)2] where P = (Fo2 + 2Fc2)/3
3594 reflections(Δ/σ)max = 0.001
262 parametersΔρmax = 0.29 e Å−3
0 restraintsΔρmin = −0.41 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
Se10.62678 (4)0.82915 (3)0.61536 (3)0.06072 (16)
O10.3614 (3)0.5213 (2)0.20388 (17)0.0633 (6)
N10.5844 (3)0.6746 (2)0.48187 (19)0.0476 (6)
N20.7071 (3)0.7047 (3)0.5160 (2)0.0587 (7)
C10.4227 (3)0.7366 (2)0.5202 (2)0.0344 (6)
C20.4117 (4)0.8232 (3)0.5918 (2)0.0395 (7)
C30.2505 (4)0.8991 (3)0.6443 (2)0.0485 (7)
H3A0.24990.99340.61630.058*
H3B0.24510.89160.71970.058*
C40.0939 (4)0.8443 (3)0.62557 (19)0.0422 (7)
H4A0.07140.76290.67360.051*
H4B−0.00570.90980.64060.051*
C50.1215 (3)0.8137 (3)0.5122 (2)0.0398 (6)
H5A0.14640.89470.46420.048*
H5B0.01690.78580.50160.048*
C60.2686 (3)0.7034 (3)0.48589 (19)0.0339 (6)
H60.23280.62100.53030.041*
C70.3076 (3)0.6729 (2)0.36983 (19)0.0331 (6)
H70.41130.60890.36040.040*
C80.3471 (3)0.7946 (3)0.28883 (18)0.0334 (6)
C90.5157 (4)0.8233 (3)0.2486 (2)0.0480 (7)
H90.60490.76710.27110.058*
C100.5519 (5)0.9349 (3)0.1752 (2)0.0606 (9)
H100.66510.95300.14930.073*
C110.4227 (5)1.0187 (3)0.1405 (2)0.0601 (9)
H110.44791.09330.09120.072*
C120.2555 (5)0.9919 (3)0.1790 (2)0.0533 (8)
H120.16691.04840.15600.064*
C130.2194 (4)0.8812 (3)0.2518 (2)0.0415 (7)
H130.10570.86390.27700.050*
C140.1634 (3)0.6015 (3)0.3511 (2)0.0376 (6)
H14A0.13200.53340.41050.045*
H14B0.06350.66620.34830.045*
C150.2124 (4)0.5363 (3)0.2507 (2)0.0375 (6)
C160.0773 (3)0.4844 (2)0.2104 (2)0.0334 (6)
C170.1294 (3)0.4041 (2)0.13129 (19)0.0358 (6)
H170.24630.38360.10480.043*
C180.0114 (3)0.3514 (2)0.08876 (19)0.0340 (6)
C19−0.1658 (3)0.3833 (3)0.12857 (19)0.0352 (6)
C20−0.2175 (3)0.4677 (3)0.2103 (2)0.0410 (7)
H20−0.33390.49060.23660.049*
C21−0.1000 (3)0.5157 (3)0.2508 (2)0.0367 (6)
H21−0.13670.56940.30550.044*
C22−0.2856 (4)0.3321 (3)0.0848 (2)0.0485 (8)
H22−0.40260.35380.10980.058*
C23−0.2302 (4)0.2516 (3)0.0068 (2)0.0550 (9)
H23−0.30950.2182−0.02140.066*
C24−0.0545 (4)0.2186 (3)−0.0316 (2)0.0532 (8)
H24−0.01840.1623−0.08450.064*
C250.0639 (4)0.2670 (3)0.0068 (2)0.0441 (7)
H250.18020.2450−0.02050.053*
U11U22U33U12U13U23
Se10.0506 (2)0.0778 (3)0.0659 (2)−0.01457 (18)−0.02624 (18)−0.01871 (18)
O10.0281 (12)0.0930 (17)0.0786 (15)−0.0050 (11)−0.0061 (11)−0.0520 (13)
N10.0352 (14)0.0520 (15)0.0575 (15)0.0042 (12)−0.0141 (12)−0.0141 (12)
N20.0365 (15)0.0715 (18)0.0714 (18)0.0003 (13)−0.0198 (14)−0.0115 (14)
C10.0340 (16)0.0341 (14)0.0349 (14)−0.0014 (12)−0.0092 (12)−0.0025 (12)
C20.0424 (17)0.0410 (15)0.0380 (15)−0.0054 (13)−0.0138 (13)−0.0049 (12)
C30.056 (2)0.0458 (17)0.0457 (17)−0.0006 (15)−0.0107 (15)−0.0160 (14)
C40.0400 (17)0.0445 (16)0.0394 (16)0.0021 (14)−0.0051 (14)−0.0081 (13)
C50.0312 (15)0.0499 (16)0.0382 (15)0.0044 (13)−0.0075 (13)−0.0130 (13)
C60.0320 (15)0.0353 (14)0.0352 (14)−0.0048 (12)−0.0076 (12)−0.0053 (11)
C70.0261 (14)0.0340 (14)0.0404 (15)0.0014 (11)−0.0080 (12)−0.0119 (12)
C80.0378 (16)0.0356 (14)0.0307 (13)−0.0041 (12)−0.0073 (12)−0.0163 (11)
C90.0389 (17)0.0519 (18)0.0536 (18)−0.0098 (14)−0.0043 (15)−0.0126 (15)
C100.061 (2)0.065 (2)0.0523 (19)−0.028 (2)0.0107 (18)−0.0137 (17)
C110.088 (3)0.051 (2)0.0368 (17)−0.017 (2)0.0017 (19)−0.0073 (15)
C120.078 (2)0.0471 (18)0.0356 (16)−0.0009 (17)−0.0170 (17)−0.0052 (14)
C130.0439 (17)0.0452 (16)0.0364 (15)−0.0020 (14)−0.0086 (13)−0.0110 (13)
C140.0313 (15)0.0372 (15)0.0463 (16)−0.0039 (12)−0.0066 (13)−0.0138 (12)
C150.0301 (16)0.0372 (15)0.0474 (16)−0.0004 (12)−0.0108 (14)−0.0114 (12)
C160.0299 (15)0.0296 (13)0.0413 (15)−0.0013 (11)−0.0090 (12)−0.0064 (12)
C170.0289 (14)0.0379 (15)0.0413 (15)0.0016 (12)−0.0093 (12)−0.0089 (12)
C180.0374 (16)0.0317 (14)0.0331 (14)−0.0025 (12)−0.0103 (12)−0.0010 (11)
C190.0359 (16)0.0373 (14)0.0337 (14)−0.0076 (12)−0.0097 (12)−0.0018 (12)
C200.0276 (15)0.0471 (16)0.0471 (16)−0.0019 (13)−0.0038 (13)−0.0106 (13)
C210.0330 (15)0.0361 (14)0.0428 (15)−0.0019 (12)−0.0068 (13)−0.0141 (12)
C220.0384 (17)0.066 (2)0.0453 (17)−0.0154 (15)−0.0092 (14)−0.0096 (15)
C230.057 (2)0.071 (2)0.0461 (17)−0.0244 (18)−0.0162 (16)−0.0134 (16)
C240.065 (2)0.061 (2)0.0414 (16)−0.0106 (17)−0.0159 (16)−0.0187 (15)
C250.0448 (18)0.0493 (17)0.0398 (16)−0.0006 (14)−0.0099 (14)−0.0135 (13)
Se1—C21.840 (3)C20—C211.362 (3)
Se1—N21.888 (3)C20—C191.417 (4)
O1—C151.214 (3)C20—H200.9300
C1—C21.355 (4)C5—H5A0.9700
C1—N11.381 (3)C5—H5B0.9700
C1—C61.509 (3)C13—C121.375 (4)
N1—N21.264 (3)C13—H130.9300
C14—C151.503 (3)C21—H210.9300
C14—C71.533 (3)C18—C251.421 (4)
C14—H14A0.9700C18—C191.411 (4)
C14—H14B0.9700C25—C241.353 (4)
C15—C161.499 (3)C25—H250.9300
C17—C161.365 (3)C9—C101.385 (4)
C17—C181.404 (3)C9—H90.9300
C17—H170.9300C19—C221.419 (3)
C7—C81.518 (3)C22—C231.356 (4)
C7—C61.546 (3)C22—H220.9300
C7—H70.9800C10—C111.369 (5)
C6—C51.526 (4)C10—H100.9300
C6—H60.9800C12—C111.373 (5)
C8—C131.386 (4)C12—H120.9300
C8—C91.392 (4)C3—H3A0.9700
C16—C211.412 (4)C3—H3B0.9700
C2—C31.488 (4)C23—C241.398 (5)
C4—C51.520 (3)C23—H230.9300
C4—C31.529 (3)C24—H240.9300
C4—H4A0.9700C11—H110.9300
C4—H4B0.9700
C2—Se1—N286.70 (11)C4—C5—C6112.0 (2)
C2—C1—N1116.2 (2)C4—C5—H5A109.2
C2—C1—C6123.1 (2)C6—C5—H5A109.2
N1—C1—C6120.6 (2)C4—C5—H5B109.2
N2—N1—C1117.3 (2)C6—C5—H5B109.2
C15—C14—C7113.2 (2)H5A—C5—H5B107.9
C15—C14—H14A108.9C12—C13—C8122.1 (3)
C7—C14—H14A108.9C12—C13—H13119.0
C15—C14—H14B108.9C8—C13—H13119.0
C7—C14—H14B108.9C20—C21—C16120.3 (2)
H14A—C14—H14B107.8C20—C21—H21119.8
O1—C15—C16119.7 (2)C16—C21—H21119.8
O1—C15—C14120.5 (2)C17—C18—C25122.4 (2)
C16—C15—C14119.8 (2)C17—C18—C19119.0 (2)
C16—C17—C18121.8 (2)C25—C18—C19118.6 (2)
C16—C17—H17119.1C24—C25—C18120.3 (3)
C18—C17—H17119.1C24—C25—H25119.9
C8—C7—C14112.5 (2)C18—C25—H25119.9
C8—C7—C6113.86 (19)C10—C9—C8120.6 (3)
C14—C7—C6110.17 (19)C10—C9—H9119.7
C8—C7—H7106.6C8—C9—H9119.7
C14—C7—H7106.6C22—C19—C20122.3 (3)
C6—C7—H7106.6C22—C19—C18119.3 (2)
N1—N2—Se1110.7 (2)C20—C19—C18118.4 (2)
C1—C6—C5108.8 (2)C23—C22—C19120.3 (3)
C1—C6—C7113.7 (2)C23—C22—H22119.9
C5—C6—C7114.0 (2)C19—C22—H22119.9
C1—C6—H6106.6C11—C10—C9120.7 (3)
C5—C6—H6106.6C11—C10—H10119.6
C7—C6—H6106.6C9—C10—H10119.7
C13—C8—C9117.2 (3)C11—C12—C13119.8 (3)
C13—C8—C7122.2 (2)C11—C12—H12120.1
C9—C8—C7120.6 (3)C13—C12—H12120.1
C17—C16—C21119.2 (2)C2—C3—C4110.6 (2)
C17—C16—C15118.1 (2)C2—C3—H3A109.5
C21—C16—C15122.7 (2)C4—C3—H3A109.5
C1—C2—C3125.2 (2)C2—C3—H3B109.5
C1—C2—Se1109.2 (2)C4—C3—H3B109.5
C3—C2—Se1125.65 (19)H3A—C3—H3B108.1
C5—C4—C3111.4 (2)C22—C23—C24120.4 (3)
C5—C4—H4A109.3C22—C23—H23119.8
C3—C4—H4A109.3C24—C23—H23119.8
C5—C4—H4B109.3C25—C24—C23121.2 (3)
C3—C4—H4B109.3C25—C24—H24119.4
H4A—C4—H4B108.0C23—C24—H24119.4
C21—C20—C19121.2 (3)C10—C11—C12119.6 (3)
C21—C20—H20119.4C10—C11—H11120.2
C19—C20—H20119.4C12—C11—H11120.2
C2—C1—N1—N2−0.6 (4)C3—C4—C5—C663.3 (3)
C6—C1—N1—N2−178.3 (2)C1—C6—C5—C4−49.3 (3)
C7—C14—C15—O113.6 (4)C7—C6—C5—C4−177.3 (2)
C7—C14—C15—C16−168.8 (2)C9—C8—C13—C12−0.5 (4)
C15—C14—C7—C867.1 (3)C7—C8—C13—C12179.5 (2)
C15—C14—C7—C6−164.7 (2)C19—C20—C21—C161.3 (4)
C1—N1—N2—Se10.9 (3)C17—C16—C21—C20−0.9 (4)
C2—Se1—N2—N1−0.8 (2)C15—C16—C21—C20179.0 (2)
C2—C1—C6—C519.6 (3)C16—C17—C18—C25−179.6 (2)
N1—C1—C6—C5−162.9 (2)C16—C17—C18—C190.4 (4)
C2—C1—C6—C7147.8 (2)C17—C18—C25—C24179.9 (3)
N1—C1—C6—C7−34.7 (3)C19—C18—C25—C24−0.1 (4)
C8—C7—C6—C1−69.0 (3)C13—C8—C9—C100.5 (4)
C14—C7—C6—C1163.5 (2)C7—C8—C9—C10−179.5 (2)
C8—C7—C6—C556.5 (3)C21—C20—C19—C22−179.9 (2)
C14—C7—C6—C5−71.0 (3)C21—C20—C19—C18−0.9 (4)
C14—C7—C8—C1339.2 (3)C17—C18—C19—C22179.1 (2)
C6—C7—C8—C13−87.1 (3)C25—C18—C19—C22−0.9 (4)
C14—C7—C8—C9−140.8 (2)C17—C18—C19—C200.0 (3)
C6—C7—C8—C992.9 (3)C25—C18—C19—C20−179.9 (2)
C18—C17—C16—C210.0 (4)C20—C19—C22—C23−179.9 (3)
C18—C17—C16—C15−179.9 (2)C18—C19—C22—C231.0 (4)
O1—C15—C16—C179.8 (4)C8—C9—C10—C11−0.3 (4)
C14—C15—C16—C17−167.9 (2)C8—C13—C12—C110.3 (4)
O1—C15—C16—C21−170.1 (3)C1—C2—C3—C412.4 (4)
C14—C15—C16—C2112.3 (4)Se1—C2—C3—C4−166.41 (18)
N1—C1—C2—C3−179.1 (2)C5—C4—C3—C2−41.7 (3)
C6—C1—C2—C3−1.5 (4)C19—C22—C23—C24−0.2 (4)
N1—C1—C2—Se1−0.1 (3)C18—C25—C24—C231.0 (4)
C6—C1—C2—Se1177.50 (18)C22—C23—C24—C25−0.8 (5)
N2—Se1—C2—C10.47 (19)C9—C10—C11—C120.1 (5)
N2—Se1—C2—C3179.4 (2)C13—C12—C11—C10−0.1 (4)
Cg is the centroid of the C16–C21 ring.
D—H···AD—HH···AD···AD—H···A
C20—H20···O1i0.932.563.381 (3)147
C22—H22···O1i0.932.583.392 (4)146
C4—H4A···Cgii0.972.633.584 (3)167
Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C16–C21 ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C20—H20⋯O1i0.932.563.381 (3)147
C22—H22⋯O1i0.932.583.392 (4)146
C4—H4A⋯Cgii0.972.633.584 (3)167

Symmetry codes: (i) ; (ii) .

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  5 in total
  1 in total

1.  Ethyl 3-(4-chloro-phen-yl)-2-phenyl-3-(4-phenyl-1,2,3-selena-diazol-5-yl)propano-ate.

Authors:  P Sugumar; S Sankari; P Manisankar; V Thiruselvam; M N Ponnuswamy
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-07-10
  1 in total

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