Literature DB >> 22412490

3,3'-[1,2-Phenyl-enebis(methyl-ene)]bis-(1-ethyl-benzimidazolium) dibromide.

Rosenani A Haque, Muhammad Adnan Iqbal, Srinivasa Budagumpi, Madhukar Hemamalini, Hoong-Kun Fun.   

Abstract

In the title mol-ecular salt, C(26)H(28)N(4) (2+)·2Br(-), the central benzene ring makes dihedral angles of 76.75 (11) and 82.40 (10)° with the pendant benzimidazole rings. The corresponding angle between the benzimidazole rings is 57.03 (9)°. In the crystal, the cations and anions are linked via C-H⋯Br hydrogen bonds, forming sheets lying parallel to the bc plane. The crystal structure also features weak C-H⋯π inter-actions.

Entities:  

Year:  2012        PMID: 22412490      PMCID: PMC3297300          DOI: 10.1107/S1600536812002802

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


Related literature

For background to the biological activities of benzimidazole compounds, see: Mohan et al. (2011 ▶).

Experimental

Crystal data

C26H28N4 2+·2Br− M = 556.34 Monoclinic, a = 9.7093 (7) Å b = 35.796 (3) Å c = 8.0340 (6) Å β = 118.230 (1)° V = 2460.1 (3) Å3 Z = 4 Mo Kα radiation μ = 3.32 mm−1 T = 296 K 0.45 × 0.32 × 0.23 mm

Data collection

Bruker APEXII DUO CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.318, T max = 0.516 16606 measured reflections 8158 independent reflections 6244 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.033 wR(F 2) = 0.080 S = 1.02 8158 reflections 291 parameters 2 restraints H-atom parameters constrained Δρmax = 0.71 e Å−3 Δρmin = −0.28 e Å−3 Absolute structure: Flack (1983 ▶), 3727 Friedel pairs Flack parameter: 0.009 (6) 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/S1600536812002802/hb6611sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002802/hb6611Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812002802/hb6611Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C26H28N42+·2BrF(000) = 1128
Mr = 556.34Dx = 1.502 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 5440 reflections
a = 9.7093 (7) Åθ = 2.9–27.3°
b = 35.796 (3) ŵ = 3.32 mm1
c = 8.0340 (6) ÅT = 296 K
β = 118.230 (1)°Block, colourless
V = 2460.1 (3) Å30.45 × 0.32 × 0.23 mm
Z = 4
Bruker APEXII DUO CCD diffractometer8158 independent reflections
Radiation source: fine-focus sealed tube6244 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
φ and ω scansθmax = 32.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −14→14
Tmin = 0.318, Tmax = 0.516k = −54→42
16606 measured reflectionsl = −12→12
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.080w = 1/[σ2(Fo2) + (0.P)2 + 0.1437P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.003
8158 reflectionsΔρmax = 0.71 e Å3
291 parametersΔρmin = −0.28 e Å3
2 restraintsAbsolute structure: Flack (1983), 3727 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.009 (6)
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Br10.68944 (3)0.918762 (6)0.48259 (3)0.05182 (7)
Br20.38351 (4)0.822199 (8)0.90664 (4)0.06457 (9)
N10.4060 (2)0.95348 (6)0.8359 (3)0.0441 (4)
N20.2014 (2)0.92236 (5)0.6352 (3)0.0378 (4)
N30.4142 (2)0.82699 (5)0.4234 (3)0.0386 (4)
N40.5754 (2)0.79004 (5)0.3842 (3)0.0416 (4)
C10.6769 (3)0.97225 (8)0.9292 (4)0.0569 (7)
H1A0.77990.97291.03540.085*
H1B0.65090.99640.87060.085*
H1C0.67390.95410.83950.085*
C20.5611 (3)0.96170 (10)0.9949 (4)0.0615 (7)
H2A0.59900.93991.07590.074*
H2B0.55190.98201.06900.074*
C30.3020 (3)0.97982 (6)0.7130 (3)0.0405 (4)
C40.3092 (3)1.01828 (7)0.7066 (4)0.0503 (6)
H4A0.39591.03160.79300.060*
C50.1818 (4)1.03575 (7)0.5662 (5)0.0578 (7)
H5A0.18261.06160.55680.069*
C60.0502 (3)1.01593 (7)0.4361 (4)0.0542 (6)
H6A−0.03331.02900.34240.065*
C70.0416 (3)0.97753 (7)0.4438 (4)0.0453 (5)
H7A−0.04610.96430.35920.054*
C80.1711 (2)0.95996 (6)0.5847 (3)0.0372 (4)
C90.3416 (3)0.92020 (6)0.7867 (3)0.0433 (5)
H9A0.38780.89810.84940.052*
C100.0966 (2)0.89051 (6)0.5423 (3)0.0388 (4)
H10A−0.00350.89520.53780.047*
H10B0.14080.86820.61740.047*
C110.0711 (3)0.88369 (5)0.3442 (3)0.0372 (4)
C12−0.0774 (3)0.89068 (6)0.1938 (4)0.0485 (5)
H12A−0.15600.89940.21870.058*
C13−0.1095 (3)0.88490 (7)0.0100 (4)0.0537 (6)
H13A−0.20820.8903−0.08860.064*
C140.0046 (4)0.87111 (7)−0.0274 (4)0.0537 (6)
H14A−0.01730.8670−0.15180.064*
C150.1523 (3)0.86321 (6)0.1182 (4)0.0478 (5)
H15A0.22890.85380.09120.057*
C160.1865 (3)0.86927 (5)0.3048 (3)0.0368 (4)
C170.3497 (3)0.86073 (6)0.4620 (4)0.0411 (5)
H17A0.41790.88170.47670.049*
H17B0.34610.85760.57980.049*
C180.3557 (3)0.79088 (6)0.4066 (3)0.0406 (5)
C190.2223 (3)0.77759 (8)0.4100 (4)0.0525 (6)
H19A0.15330.79330.42600.063*
C200.1996 (4)0.73945 (9)0.3877 (5)0.0635 (8)
H20A0.11120.72920.38650.076*
C210.3028 (4)0.71617 (7)0.3674 (5)0.0665 (8)
H21A0.28250.69060.35470.080*
C220.4359 (4)0.72922 (7)0.3652 (4)0.0581 (7)
H22A0.50600.71330.35230.070*
C230.4582 (3)0.76776 (6)0.3837 (3)0.0404 (4)
C240.5441 (3)0.82501 (6)0.4069 (3)0.0406 (5)
H24A0.60470.84550.41080.049*
C250.7016 (3)0.77625 (9)0.3487 (5)0.0621 (7)
H25A0.65590.76460.22510.074*
H25B0.76020.75730.44180.074*
C260.8105 (5)0.80600 (13)0.3563 (8)0.0893 (12)
H26A0.87820.79640.30990.134*
H26B0.87200.81420.48450.134*
H26C0.75180.82670.27950.134*
U11U22U33U12U13U23
Br10.05117 (12)0.04447 (12)0.05944 (14)0.00068 (11)0.02585 (11)0.00191 (11)
Br20.0914 (2)0.05391 (15)0.06103 (16)0.03112 (14)0.04636 (15)0.01796 (12)
N10.0401 (9)0.0531 (11)0.0364 (9)0.0054 (8)0.0158 (8)0.0004 (8)
N20.0395 (9)0.0323 (8)0.0399 (9)0.0074 (7)0.0174 (8)0.0014 (7)
N30.0384 (9)0.0314 (8)0.0517 (10)0.0024 (7)0.0261 (9)0.0025 (7)
N40.0413 (10)0.0384 (9)0.0485 (10)0.0098 (7)0.0240 (8)0.0037 (8)
C10.0458 (13)0.0531 (14)0.0583 (16)0.0057 (11)0.0136 (13)0.0064 (11)
C20.0454 (13)0.085 (2)0.0391 (13)0.0005 (14)0.0076 (11)−0.0018 (12)
C30.0437 (11)0.0399 (10)0.0417 (11)0.0040 (9)0.0234 (9)−0.0029 (8)
C40.0533 (13)0.0392 (11)0.0636 (15)−0.0033 (10)0.0319 (12)−0.0091 (10)
C50.0717 (17)0.0332 (11)0.0821 (19)0.0063 (11)0.0475 (16)0.0009 (11)
C60.0530 (13)0.0404 (12)0.0704 (17)0.0135 (11)0.0301 (13)0.0089 (11)
C70.0398 (11)0.0415 (11)0.0506 (13)0.0100 (9)0.0182 (10)0.0021 (9)
C80.0398 (10)0.0326 (9)0.0416 (11)0.0065 (8)0.0213 (9)0.0005 (8)
C90.0447 (11)0.0423 (11)0.0413 (11)0.0091 (9)0.0192 (10)0.0043 (8)
C100.0378 (10)0.0335 (10)0.0506 (12)0.0034 (8)0.0253 (10)0.0000 (8)
C110.0411 (10)0.0255 (8)0.0473 (11)0.0003 (7)0.0229 (9)−0.0004 (7)
C120.0438 (12)0.0378 (11)0.0579 (14)0.0073 (9)0.0191 (11)−0.0024 (10)
C130.0534 (14)0.0394 (11)0.0517 (14)0.0041 (11)0.0112 (12)−0.0014 (10)
C140.0760 (18)0.0378 (11)0.0438 (13)−0.0009 (12)0.0253 (13)−0.0006 (9)
C150.0660 (15)0.0352 (10)0.0530 (13)0.0019 (10)0.0370 (12)−0.0005 (9)
C160.0444 (11)0.0245 (8)0.0466 (11)0.0015 (8)0.0257 (9)0.0028 (7)
C170.0425 (11)0.0352 (10)0.0523 (13)0.0060 (9)0.0279 (10)−0.0028 (9)
C180.0440 (11)0.0339 (10)0.0459 (11)−0.0011 (8)0.0229 (10)0.0035 (8)
C190.0524 (14)0.0476 (13)0.0659 (16)−0.0074 (11)0.0348 (13)0.0019 (11)
C200.0695 (18)0.0507 (15)0.0742 (18)−0.0191 (14)0.0372 (15)0.0068 (13)
C210.088 (2)0.0359 (12)0.0665 (17)−0.0097 (14)0.0293 (17)0.0035 (12)
C220.0764 (19)0.0329 (11)0.0570 (15)0.0096 (12)0.0249 (14)0.0031 (10)
C230.0451 (11)0.0337 (9)0.0393 (11)0.0056 (9)0.0174 (9)0.0034 (8)
C240.0373 (10)0.0367 (10)0.0523 (13)0.0014 (8)0.0249 (10)0.0022 (9)
C250.0527 (14)0.0677 (17)0.0768 (19)0.0179 (13)0.0396 (14)−0.0038 (14)
C260.065 (2)0.100 (3)0.133 (3)−0.0016 (19)0.071 (2)−0.011 (3)
N1—C91.316 (3)C10—H10B0.9700
N1—C31.393 (3)C11—C121.397 (3)
N1—C21.472 (3)C11—C161.399 (3)
N2—C91.332 (3)C12—C131.373 (4)
N2—C81.396 (3)C12—H12A0.9300
N2—C101.474 (3)C13—C141.369 (5)
N3—C241.331 (3)C13—H13A0.9300
N3—C181.393 (3)C14—C151.385 (4)
N3—C171.460 (3)C14—H14A0.9300
N4—C241.321 (3)C15—C161.391 (3)
N4—C231.388 (3)C15—H15A0.9300
N4—C251.469 (3)C16—C171.519 (3)
C1—C21.499 (5)C17—H17A0.9700
C1—H1A0.9600C17—H17B0.9700
C1—H1B0.9600C18—C231.372 (3)
C1—H1C0.9600C18—C191.392 (4)
C2—H2A0.9700C19—C201.381 (4)
C2—H2B0.9700C19—H19A0.9300
C3—C41.381 (3)C20—C211.371 (5)
C3—C81.394 (3)C20—H20A0.9300
C4—C51.368 (4)C21—C221.382 (5)
C4—H4A0.9300C21—H21A0.9300
C5—C61.402 (4)C22—C231.393 (3)
C5—H5A0.9300C22—H22A0.9300
C6—C71.380 (4)C24—H24A0.9300
C6—H6A0.9300C25—C261.481 (5)
C7—C81.383 (3)C25—H25A0.9700
C7—H7A0.9300C25—H25B0.9700
C9—H9A0.9300C26—H26A0.9600
C10—C111.510 (3)C26—H26B0.9600
C10—H10A0.9700C26—H26C0.9600
C9—N1—C3108.49 (19)C13—C12—C11121.3 (3)
C9—N1—C2126.0 (2)C13—C12—H12A119.3
C3—N1—C2125.5 (2)C11—C12—H12A119.3
C9—N2—C8107.76 (18)C14—C13—C12119.6 (2)
C9—N2—C10125.46 (17)C14—C13—H13A120.2
C8—N2—C10126.77 (18)C12—C13—H13A120.2
C24—N3—C18107.65 (19)C13—C14—C15120.7 (3)
C24—N3—C17125.96 (19)C13—C14—H14A119.6
C18—N3—C17126.3 (2)C15—C14—H14A119.6
C24—N4—C23107.7 (2)C14—C15—C16120.1 (2)
C24—N4—C25127.8 (2)C14—C15—H15A119.9
C23—N4—C25124.4 (2)C16—C15—H15A119.9
C2—C1—H1A109.5C15—C16—C11119.6 (2)
C2—C1—H1B109.5C15—C16—C17119.2 (2)
H1A—C1—H1B109.5C11—C16—C17121.2 (2)
C2—C1—H1C109.5N3—C17—C16111.95 (19)
H1A—C1—H1C109.5N3—C17—H17A109.2
H1B—C1—H1C109.5C16—C17—H17A109.2
N1—C2—C1112.0 (2)N3—C17—H17B109.2
N1—C2—H2A109.2C16—C17—H17B109.2
C1—C2—H2A109.2H17A—C17—H17B107.9
N1—C2—H2B109.2C23—C18—C19122.5 (2)
C1—C2—H2B109.2C23—C18—N3106.5 (2)
H2A—C2—H2B107.9C19—C18—N3131.0 (2)
C4—C3—N1132.0 (2)C20—C19—C18115.4 (3)
C4—C3—C8121.7 (2)C20—C19—H19A122.3
N1—C3—C8106.29 (19)C18—C19—H19A122.3
C5—C4—C3116.4 (2)C21—C20—C19122.4 (3)
C5—C4—H4A121.8C21—C20—H20A118.8
C3—C4—H4A121.8C19—C20—H20A118.8
C4—C5—C6122.2 (2)C20—C21—C22122.4 (2)
C4—C5—H5A118.9C20—C21—H21A118.8
C6—C5—H5A118.9C22—C21—H21A118.8
C7—C6—C5121.6 (2)C21—C22—C23115.6 (3)
C7—C6—H6A119.2C21—C22—H22A122.2
C5—C6—H6A119.2C23—C22—H22A122.2
C6—C7—C8116.0 (2)C18—C23—N4107.35 (18)
C6—C7—H7A122.0C18—C23—C22121.7 (3)
C8—C7—H7A122.0N4—C23—C22130.9 (2)
C7—C8—C3122.1 (2)N4—C24—N3110.8 (2)
C7—C8—N2131.4 (2)N4—C24—H24A124.6
C3—C8—N2106.51 (18)N3—C24—H24A124.6
N1—C9—N2110.93 (19)N4—C25—C26113.3 (3)
N1—C9—H9A124.5N4—C25—H25A108.9
N2—C9—H9A124.5C26—C25—H25A108.9
N2—C10—C11112.86 (18)N4—C25—H25B108.9
N2—C10—H10A109.0C26—C25—H25B108.9
C11—C10—H10A109.0H25A—C25—H25B107.7
N2—C10—H10B109.0C25—C26—H26A109.5
C11—C10—H10B109.0C25—C26—H26B109.5
H10A—C10—H10B107.8H26A—C26—H26B109.5
C12—C11—C16118.6 (2)C25—C26—H26C109.5
C12—C11—C10118.1 (2)H26A—C26—H26C109.5
C16—C11—C10123.2 (2)H26B—C26—H26C109.5
C9—N1—C2—C1108.0 (3)C14—C15—C16—C17−179.4 (2)
C3—N1—C2—C1−72.7 (3)C12—C11—C16—C151.7 (3)
C9—N1—C3—C4177.2 (3)C10—C11—C16—C15178.9 (2)
C2—N1—C3—C4−2.3 (4)C12—C11—C16—C17−179.5 (2)
C9—N1—C3—C8−0.8 (3)C10—C11—C16—C17−2.3 (3)
C2—N1—C3—C8179.8 (2)C24—N3—C17—C16119.9 (3)
N1—C3—C4—C5−178.5 (3)C18—N3—C17—C16−63.6 (3)
C8—C3—C4—C5−0.8 (4)C15—C16—C17—N3−38.6 (3)
C3—C4—C5—C60.4 (4)C11—C16—C17—N3142.5 (2)
C4—C5—C6—C70.6 (5)C24—N3—C18—C231.2 (3)
C5—C6—C7—C8−1.1 (4)C17—N3—C18—C23−175.9 (2)
C6—C7—C8—C30.8 (4)C24—N3—C18—C19−178.7 (3)
C6—C7—C8—N2178.7 (3)C17—N3—C18—C194.2 (4)
C4—C3—C8—C70.2 (4)C23—C18—C19—C20−0.3 (4)
N1—C3—C8—C7178.4 (2)N3—C18—C19—C20179.6 (3)
C4—C3—C8—N2−178.2 (2)C18—C19—C20—C211.2 (5)
N1—C3—C8—N20.0 (3)C19—C20—C21—C22−0.9 (5)
C9—N2—C8—C7−177.4 (3)C20—C21—C22—C23−0.4 (5)
C10—N2—C8—C71.1 (4)C19—C18—C23—N4179.1 (2)
C9—N2—C8—C30.8 (3)N3—C18—C23—N4−0.8 (3)
C10—N2—C8—C3179.3 (2)C19—C18—C23—C22−1.0 (4)
C3—N1—C9—N21.4 (3)N3—C18—C23—C22179.0 (2)
C2—N1—C9—N2−179.2 (2)C24—N4—C23—C180.1 (3)
C8—N2—C9—N1−1.4 (3)C25—N4—C23—C18−175.1 (2)
C10—N2—C9—N1−179.9 (2)C24—N4—C23—C22−179.7 (3)
C9—N2—C10—C11−114.9 (2)C25—N4—C23—C225.0 (4)
C8—N2—C10—C1166.8 (3)C21—C22—C23—C181.4 (4)
N2—C10—C11—C12−111.6 (2)C21—C22—C23—N4−178.8 (3)
N2—C10—C11—C1671.3 (2)C23—N4—C24—N30.7 (3)
C16—C11—C12—C13−2.3 (3)C25—N4—C24—N3175.7 (3)
C10—C11—C12—C13−179.6 (2)C18—N3—C24—N4−1.2 (3)
C11—C12—C13—C141.7 (4)C17—N3—C24—N4175.9 (2)
C12—C13—C14—C15−0.5 (4)C24—N4—C25—C265.3 (5)
C13—C14—C15—C160.0 (4)C23—N4—C25—C26179.6 (3)
C14—C15—C16—C11−0.6 (3)
D—H···AD—HH···AD···AD—H···A
C9—H9A···Br20.932.763.610 (2)152
C10—H10A···Br1i0.972.923.884 (2)171
C10—H10B···Br20.972.913.820 (2)156
C15—H15A···Br2ii0.932.803.700 (3)163
C17—H17B···Br20.972.783.696 (3)158
C24—H24A···Br10.932.733.579 (2)152
C5—H5A···Cg4iii0.932.923.630 (3)135
Table 1

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C11–C16 ring.

D—H⋯AD—HH⋯ADAD—H⋯A
C9—H9A⋯Br20.932.763.610 (2)152
C10—H10A⋯Br1i0.972.923.884 (2)171
C10—H10B⋯Br20.972.913.820 (2)156
C15—H15A⋯Br2ii0.932.803.700 (3)163
C17—H17B⋯Br20.972.783.696 (3)158
C24—H24A⋯Br10.932.733.579 (2)152
C5—H5ACg4iii0.932.923.630 (3)135

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

  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  2 in total
  6 in total

1.  Design, synthesis and structural studies of meta-xylyl linked bis-benzimidazolium salts: potential anticancer agents against 'human colon cancer'.

Authors:  Rosenani A Haque; Muhammad Adnan Iqbal; Mohamed B Khadeer Ahamed; Ams Abdul Majid; Zena A Abdul Hameed
Journal:  Chem Cent J       Date:  2012-07-18       Impact factor: 4.215

2.  3,3'-[1,4-Phenyl-enebis(methyl-ene)]-bis-(1-propyl-benzimidazolium) dichloride dihydrate.

Authors:  Rosenani A Haque; Muhammad Adnan Iqbal; Safaa A Ahmad; Tze Shyang Chia; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-02-24

3.  3,3'-Dicyclo-pentyl-1,1'-(1,3-phenyl-enedimethyl-ene)dibenzimidazol-1-ium bis-(hexa-fluoro-phosphate).

Authors:  Rosenani A Haque; S Fatimah Nasri; Mohd Mustaqim Rosli; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-05-23

4.  3,3'-[1,2-Phenyl-enebis(methyl-ene)]bis-(1-octylbenzimidazolium) dibromide monohydrate.

Authors:  Rosenani A Haque; Muhammad Adnan Iqbal; Hoong-Kun Fun; Suhana Arshad
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-03-03

5.  Potential of silver against human colon cancer: (synthesis, characterization and crystal structures of xylyl (Ortho, meta, &Para) linked bis-benzimidazolium salts and Ag(I)-NHC complexes: In vitro anticancer studies).

Authors:  Muhammad Adnan Iqbal; Rosenani A Haque; Siti Fatimah Nasri; Ams Abdul Majid; Mohamed B Khadeer Ahamed; Elham Farsi; Tabinda Fatima
Journal:  Chem Cent J       Date:  2013-02-07       Impact factor: 4.215

6.  Crystal structure of benzimidazolium salicylate.

Authors:  M Amudha; P Praveen Kumar; G Chakkaravarthi
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-09-26
  6 in total

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