Literature DB >> 22199864

5-(4,4''-Difluoro-5'-hy-droxy-1,1':3',1''-terphenyl-4'-yl)-3-(morpholin-4-ylmeth-yl)-1,3,4-oxadiazole-2(3H)-thione.

Hoong-Kun Fun, Suhana Arshad, S Samshuddin, B Narayana, B K Sarojini.   

Abstract

In the title compound, C(25)H(21)F(2)N(3)O(3)S, the morpholine ring adopts a chair conformation. The 1,3,4-oxadiazole-2(3H)-thione group makes dihedral angles of 78.69 (8), 53.56 (7) and 55.30 (9)° with the benzene rings. In the crystal, O-H⋯O, C-H⋯S and C-H⋯F hydrogen bonds linked the mol-ecules into layers lying parallel to the ab plane. Weak C-H⋯π inter-actions also occur.

Entities:  

Year:  2011        PMID: 22199864      PMCID: PMC3239015          DOI: 10.1107/S1600536811048471

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


Related literature

For pharmacological background, see: Bhatia & Gupta (2011 ▶); Liu (2006 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C25H21F2N3O3S M = 481.51 Monoclinic, a = 16.0547 (14) Å b = 11.4125 (11) Å c = 25.364 (2) Å β = 94.202 (2)° V = 4634.9 (7) Å3 Z = 8 Mo Kα radiation μ = 0.19 mm−1 T = 296 K 0.48 × 0.25 × 0.17 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.916, T max = 0.969 23057 measured reflections 6182 independent reflections 4139 reflections with I > 2σ(I) R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.143 S = 1.03 6182 reflections 311 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.24 e Å−3 Δρmin = −0.24 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811048471/hb6502sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048471/hb6502Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811048471/hb6502Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C25H21F2N3O3SF(000) = 2000
Mr = 481.51Dx = 1.380 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 6002 reflections
a = 16.0547 (14) Åθ = 2.3–27.3°
b = 11.4125 (11) ŵ = 0.19 mm1
c = 25.364 (2) ÅT = 296 K
β = 94.202 (2)°Block, colourless
V = 4634.9 (7) Å30.48 × 0.25 × 0.17 mm
Z = 8
Bruker SMART APEXII DUO CCD area-detector diffractometer6182 independent reflections
Radiation source: fine-focus sealed tube4139 reflections with I > 2σ(I)
graphiteRint = 0.029
φ and ω scansθmax = 29.1°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −20→21
Tmin = 0.916, Tmax = 0.969k = −15→14
23057 measured reflectionsl = −34→34
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0688P)2 + 1.531P] where P = (Fo2 + 2Fc2)/3
6182 reflections(Δ/σ)max < 0.001
311 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = −0.24 e Å3
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
S10.15583 (3)0.82030 (5)0.44595 (2)0.06259 (17)
F10.77333 (9)0.33903 (13)0.20221 (6)0.0943 (5)
F20.46943 (11)1.25156 (10)0.31200 (6)0.1043 (5)
O10.29532 (7)0.74319 (10)0.40602 (4)0.0469 (3)
O20.38526 (11)1.29292 (12)0.42547 (7)0.0812 (5)
O30.39200 (10)0.53070 (12)0.41580 (6)0.0697 (5)
N10.39553 (9)0.85596 (11)0.44436 (5)0.0439 (3)
N20.31768 (8)0.88887 (11)0.45963 (5)0.0420 (3)
N30.32987 (9)1.09806 (11)0.48147 (6)0.0462 (3)
C10.64272 (12)0.56922 (18)0.24724 (7)0.0583 (5)
H1A0.62430.64330.23660.070*
C20.69619 (13)0.5084 (2)0.21659 (8)0.0673 (6)
H2A0.71410.54110.18580.081*
C30.72171 (12)0.4003 (2)0.23261 (8)0.0616 (5)
C40.69747 (13)0.34894 (18)0.27745 (9)0.0635 (5)
H4A0.71610.27440.28730.076*
C50.64462 (12)0.41028 (16)0.30795 (8)0.0569 (5)
H5A0.62770.37640.33880.068*
C60.61605 (10)0.52180 (14)0.29362 (6)0.0456 (4)
C70.55723 (10)0.58586 (14)0.32581 (6)0.0451 (4)
C80.50339 (11)0.52572 (14)0.35719 (7)0.0504 (4)
H8A0.50620.44450.35940.061*
C90.44575 (11)0.58574 (14)0.38513 (7)0.0498 (4)
C100.43949 (10)0.70772 (13)0.38186 (6)0.0432 (4)
C110.49340 (10)0.76946 (13)0.35017 (6)0.0428 (4)
C120.55155 (11)0.70777 (14)0.32334 (7)0.0473 (4)
H12A0.58780.74880.30310.057*
C130.48645 (11)0.89862 (13)0.34198 (6)0.0442 (4)
C140.41390 (13)0.94776 (16)0.31948 (8)0.0605 (5)
H14A0.36800.89980.31110.073*
C150.40759 (16)1.06664 (18)0.30901 (9)0.0715 (6)
H15A0.35851.09870.29350.086*
C160.47502 (17)1.13499 (16)0.32200 (9)0.0669 (6)
C170.54758 (16)1.09168 (18)0.34457 (10)0.0725 (6)
H17A0.59251.14120.35330.087*
C180.55406 (13)0.97158 (16)0.35447 (8)0.0591 (5)
H18A0.60380.94050.36950.071*
C190.37959 (10)0.77082 (13)0.41218 (6)0.0410 (3)
C200.25662 (11)0.82095 (14)0.43819 (6)0.0434 (4)
C210.30977 (12)0.98278 (14)0.49890 (7)0.0497 (4)
H21A0.25280.98330.50930.060*
H21B0.34600.96430.53010.060*
C220.28404 (13)1.13579 (17)0.43316 (8)0.0602 (5)
H22A0.22491.12040.43520.072*
H22B0.30301.09270.40330.072*
C230.29823 (15)1.26587 (18)0.42564 (9)0.0719 (6)
H23A0.26981.29080.39250.086*
H23B0.27441.30880.45390.086*
C240.42904 (15)1.25413 (18)0.47370 (12)0.0814 (7)
H24A0.40741.29460.50340.098*
H24B0.48791.27290.47310.098*
C250.41867 (12)1.12362 (16)0.48025 (10)0.0644 (5)
H25A0.44141.08250.45100.077*
H25B0.44841.09780.51290.077*
H1O30.3975 (15)0.462 (2)0.4167 (10)0.085 (8)*
U11U22U33U12U13U23
S10.0450 (3)0.0795 (4)0.0650 (3)−0.0045 (2)0.0151 (2)0.0078 (2)
F10.0814 (9)0.1175 (12)0.0876 (9)0.0413 (8)0.0312 (7)−0.0178 (8)
F20.1615 (16)0.0372 (6)0.1162 (11)−0.0069 (7)0.0247 (11)0.0151 (7)
O10.0495 (7)0.0439 (6)0.0489 (6)−0.0027 (5)0.0138 (5)−0.0051 (5)
O20.0963 (12)0.0428 (7)0.1116 (12)0.0026 (7)0.0566 (10)0.0151 (8)
O30.0916 (11)0.0357 (7)0.0894 (10)−0.0003 (7)0.0576 (9)0.0079 (6)
N10.0444 (7)0.0367 (7)0.0522 (7)−0.0046 (5)0.0149 (6)−0.0034 (6)
N20.0448 (8)0.0333 (6)0.0500 (7)−0.0026 (5)0.0170 (6)−0.0023 (5)
N30.0476 (8)0.0344 (7)0.0585 (8)0.0001 (6)0.0167 (6)−0.0009 (6)
C10.0570 (11)0.0596 (11)0.0609 (10)0.0109 (9)0.0209 (9)0.0060 (9)
C20.0602 (13)0.0873 (15)0.0574 (10)0.0148 (11)0.0241 (9)0.0043 (10)
C30.0450 (10)0.0789 (14)0.0621 (11)0.0153 (9)0.0114 (8)−0.0157 (10)
C40.0587 (12)0.0581 (11)0.0748 (13)0.0153 (9)0.0117 (10)−0.0077 (10)
C50.0599 (11)0.0527 (10)0.0597 (10)0.0059 (8)0.0163 (9)0.0002 (8)
C60.0416 (9)0.0453 (9)0.0509 (8)0.0004 (7)0.0105 (7)−0.0044 (7)
C70.0450 (9)0.0416 (8)0.0501 (8)−0.0016 (7)0.0129 (7)−0.0034 (7)
C80.0615 (11)0.0322 (8)0.0603 (10)0.0012 (7)0.0230 (8)0.0000 (7)
C90.0603 (11)0.0364 (8)0.0557 (9)−0.0037 (7)0.0249 (8)0.0004 (7)
C100.0481 (9)0.0341 (8)0.0492 (8)−0.0036 (6)0.0165 (7)−0.0048 (6)
C110.0440 (9)0.0343 (8)0.0513 (8)−0.0074 (6)0.0123 (7)−0.0036 (6)
C120.0454 (9)0.0416 (8)0.0569 (9)−0.0088 (7)0.0179 (8)−0.0020 (7)
C130.0510 (10)0.0348 (8)0.0488 (8)−0.0092 (7)0.0174 (7)−0.0038 (6)
C140.0619 (12)0.0458 (10)0.0732 (12)−0.0109 (9)0.0013 (10)0.0040 (9)
C150.0857 (16)0.0513 (11)0.0769 (13)0.0032 (11)0.0012 (12)0.0133 (10)
C160.0993 (17)0.0350 (9)0.0689 (12)−0.0083 (10)0.0234 (12)0.0032 (8)
C170.0840 (16)0.0447 (11)0.0906 (15)−0.0277 (11)0.0186 (13)−0.0078 (10)
C180.0573 (11)0.0458 (10)0.0753 (12)−0.0151 (8)0.0122 (9)−0.0045 (9)
C190.0456 (9)0.0325 (7)0.0464 (8)−0.0056 (6)0.0137 (7)0.0005 (6)
C200.0472 (9)0.0408 (8)0.0434 (8)−0.0030 (7)0.0127 (7)0.0057 (6)
C210.0621 (11)0.0389 (8)0.0509 (9)−0.0035 (7)0.0232 (8)−0.0050 (7)
C220.0640 (12)0.0498 (10)0.0677 (12)0.0024 (9)0.0110 (10)0.0033 (9)
C230.0871 (16)0.0531 (11)0.0778 (13)0.0152 (11)0.0208 (12)0.0155 (10)
C240.0629 (13)0.0455 (11)0.139 (2)−0.0091 (9)0.0271 (15)0.0061 (13)
C250.0505 (11)0.0415 (10)0.1024 (16)−0.0016 (8)0.0153 (10)0.0027 (10)
S1—C201.6445 (17)C8—H8A0.9300
F1—C31.365 (2)C9—C101.398 (2)
F2—C161.356 (2)C10—C111.412 (2)
O1—C201.3834 (18)C10—C191.464 (2)
O1—C191.3868 (19)C11—C121.387 (2)
O2—C231.431 (3)C11—C131.492 (2)
O2—C241.436 (3)C12—H12A0.9300
O3—C91.3577 (18)C13—C141.378 (3)
O3—H1O30.78 (3)C13—C181.386 (2)
N1—C191.283 (2)C14—C151.385 (3)
N1—N21.3871 (18)C14—H14A0.9300
N2—C201.334 (2)C15—C161.355 (3)
N2—C211.4749 (19)C15—H15A0.9300
N3—C211.432 (2)C16—C171.353 (3)
N3—C221.448 (3)C17—C181.396 (3)
N3—C251.458 (2)C17—H17A0.9300
C1—C21.386 (2)C18—H18A0.9300
C1—C61.391 (2)C21—H21A0.9700
C1—H1A0.9300C21—H21B0.9700
C2—C31.353 (3)C22—C231.516 (3)
C2—H2A0.9300C22—H22A0.9700
C3—C41.362 (3)C22—H22B0.9700
C4—C51.380 (2)C23—H23A0.9700
C4—H4A0.9300C23—H23B0.9700
C5—C61.392 (2)C24—C251.509 (3)
C5—H5A0.9300C24—H24A0.9700
C6—C71.485 (2)C24—H24B0.9700
C7—C121.395 (2)C25—H25A0.9700
C7—C81.397 (2)C25—H25B0.9700
C8—C91.387 (2)
C20—O1—C19105.32 (12)C13—C14—H14A119.1
C23—O2—C24110.36 (15)C15—C14—H14A119.1
C9—O3—H1O3113.7 (18)C16—C15—C14118.1 (2)
C19—N1—N2103.95 (13)C16—C15—H15A120.9
C20—N2—N1112.27 (12)C14—C15—H15A120.9
C20—N2—C21126.91 (14)C17—C16—C15122.69 (18)
N1—N2—C21120.62 (13)C17—C16—F2118.7 (2)
C21—N3—C22114.98 (15)C15—C16—F2118.6 (2)
C21—N3—C25115.67 (14)C16—C17—C18119.03 (19)
C22—N3—C25111.09 (15)C16—C17—H17A120.5
C2—C1—C6121.44 (18)C18—C17—H17A120.5
C2—C1—H1A119.3C13—C18—C17120.1 (2)
C6—C1—H1A119.3C13—C18—H18A119.9
C3—C2—C1118.32 (18)C17—C18—H18A119.9
C3—C2—H2A120.8N1—C19—O1113.05 (13)
C1—C2—H2A120.8N1—C19—C10126.79 (15)
C2—C3—C4123.01 (17)O1—C19—C10120.12 (13)
C2—C3—F1118.72 (18)N2—C20—O1105.36 (13)
C4—C3—F1118.27 (19)N2—C20—S1130.84 (12)
C3—C4—C5118.36 (19)O1—C20—S1123.79 (12)
C3—C4—H4A120.8N3—C21—N2115.25 (13)
C5—C4—H4A120.8N3—C21—H21A108.5
C4—C5—C6121.45 (17)N2—C21—H21A108.5
C4—C5—H5A119.3N3—C21—H21B108.5
C6—C5—H5A119.3N2—C21—H21B108.5
C1—C6—C5117.43 (15)H21A—C21—H21B107.5
C1—C6—C7121.40 (15)N3—C22—C23109.02 (18)
C5—C6—C7121.14 (15)N3—C22—H22A109.9
C12—C7—C8118.31 (14)C23—C22—H22A109.9
C12—C7—C6120.54 (14)N3—C22—H22B109.9
C8—C7—C6121.07 (14)C23—C22—H22B109.9
C9—C8—C7120.80 (15)H22A—C22—H22B108.3
C9—C8—H8A119.6O2—C23—C22111.55 (16)
C7—C8—H8A119.6O2—C23—H23A109.3
O3—C9—C8122.70 (15)C22—C23—H23A109.3
O3—C9—C10116.67 (14)O2—C23—H23B109.3
C8—C9—C10120.62 (14)C22—C23—H23B109.3
C9—C10—C11119.10 (14)H23A—C23—H23B108.0
C9—C10—C19120.39 (13)O2—C24—C25110.3 (2)
C11—C10—C19120.48 (14)O2—C24—H24A109.6
C12—C11—C10119.26 (14)C25—C24—H24A109.6
C12—C11—C13118.65 (13)O2—C24—H24B109.6
C10—C11—C13121.99 (13)C25—C24—H24B109.6
C11—C12—C7121.89 (14)H24A—C24—H24B108.1
C11—C12—H12A119.1N3—C25—C24108.40 (16)
C7—C12—H12A119.1N3—C25—H25A110.0
C14—C13—C18118.30 (16)C24—C25—H25A110.0
C14—C13—C11120.80 (15)N3—C25—H25B110.0
C18—C13—C11120.83 (17)C24—C25—H25B110.0
C13—C14—C15121.73 (19)H25A—C25—H25B108.4
C19—N1—N2—C202.31 (17)C18—C13—C14—C150.4 (3)
C19—N1—N2—C21177.47 (14)C11—C13—C14—C15−176.60 (18)
C6—C1—C2—C30.5 (3)C13—C14—C15—C16−0.6 (3)
C1—C2—C3—C4−0.2 (3)C14—C15—C16—C170.1 (3)
C1—C2—C3—F1178.97 (19)C14—C15—C16—F2−179.89 (19)
C2—C3—C4—C5−0.2 (3)C15—C16—C17—C180.7 (3)
F1—C3—C4—C5−179.36 (19)F2—C16—C17—C18−179.34 (19)
C3—C4—C5—C60.2 (3)C14—C13—C18—C170.4 (3)
C2—C1—C6—C5−0.5 (3)C11—C13—C18—C17177.39 (17)
C2—C1—C6—C7−178.59 (18)C16—C17—C18—C13−0.9 (3)
C4—C5—C6—C10.1 (3)N2—N1—C19—O1−1.38 (17)
C4—C5—C6—C7178.19 (18)N2—N1—C19—C10176.19 (14)
C1—C6—C7—C12−24.7 (3)C20—O1—C19—N10.08 (17)
C5—C6—C7—C12157.23 (18)C20—O1—C19—C10−177.68 (13)
C1—C6—C7—C8152.03 (18)C9—C10—C19—N1125.76 (19)
C5—C6—C7—C8−26.0 (3)C11—C10—C19—N1−52.3 (2)
C12—C7—C8—C90.0 (3)C9—C10—C19—O1−56.8 (2)
C6—C7—C8—C9−176.80 (17)C11—C10—C19—O1125.07 (16)
C7—C8—C9—O3179.61 (18)N1—N2—C20—O1−2.28 (16)
C7—C8—C9—C100.9 (3)C21—N2—C20—O1−177.07 (14)
O3—C9—C10—C11−179.50 (17)N1—N2—C20—S1176.89 (12)
C8—C9—C10—C11−0.8 (3)C21—N2—C20—S12.1 (2)
O3—C9—C10—C192.4 (3)C19—O1—C20—N21.33 (15)
C8—C9—C10—C19−178.88 (17)C19—O1—C20—S1−177.92 (12)
C9—C10—C11—C12−0.4 (3)C22—N3—C21—N254.9 (2)
C19—C10—C11—C12177.73 (16)C25—N3—C21—N2−76.8 (2)
C9—C10—C11—C13175.85 (17)C20—N2—C21—N3−116.90 (18)
C19—C10—C11—C13−6.0 (3)N1—N2—C21—N368.7 (2)
C10—C11—C12—C71.4 (3)C21—N3—C22—C23168.57 (15)
C13—C11—C12—C7−174.96 (17)C25—N3—C22—C23−57.65 (19)
C8—C7—C12—C11−1.2 (3)C24—O2—C23—C22−57.5 (2)
C6—C7—C12—C11175.63 (16)N3—C22—C23—O256.2 (2)
C12—C11—C13—C14116.54 (19)C23—O2—C24—C2559.3 (2)
C10—C11—C13—C14−59.7 (2)C21—N3—C25—C24−166.88 (18)
C12—C11—C13—C18−60.4 (2)C22—N3—C25—C2459.7 (2)
C10—C11—C13—C18123.36 (18)O2—C24—C25—N3−59.7 (2)
Cg1 is the centroid of the C7–C12 ring.
D—H···AD—HH···AD···AD—H···A
O3—H1O3···O2i0.79 (2)1.95 (2)2.728 (2)167 (2)
C5—H5A···S1ii0.932.803.639 (2)151
C12—H12A···F1iii0.932.473.292 (2)148
C23—H23A···F1iv0.972.513.462 (3)167
C1—H1A···Cg1v0.932.913.414 (2)115
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 ring.

D—H⋯AD—HH⋯ADAD—H⋯A
O3—H1O3⋯O2i0.79 (2)1.95 (2)2.728 (2)167 (2)
C5—H5A⋯S1ii0.932.803.639 (2)151
C12—H12A⋯F1iii0.932.473.292 (2)148
C23—H23A⋯F1iv0.972.513.462 (3)167
C1—H1ACg1v0.932.913.414 (2)115

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

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