Literature DB >> 21589297

(2,2'-Biquinoline-κN,N')dibromido-zinc(II).

Hamideh Saravani1, Ali Reza Rezvani, Niloufar Akbarzadeh Torbati.   

Abstract

In the title compound, [ZnBr(2)(C(18)H(12)N(2))], the Zn(II) atom is four-coordinated in a distorted tetra-hedral configuration by two N atoms from the 2,2'-biquinoline ligand and two terminal Br atoms. The crystal packing is stabilized by weak inter-molecular C-H⋯Br hydrogen bonds and extensive inter-molecular π-π contacts between the pyridine and benzene rings [centroid-centroid distances = 3.775 (4), 3.748 (4), 3.735 (4), 3.538 (4), 3.678 (4) and 3.513 (4) Å].

Entities:  

Year:  2010        PMID： 21589297      PMCID： PMC3011677          DOI： 10.1107/S1600536810047434

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


Related literature

For Zn—Br and Zn—N bond lengths in related structures, see: Alizadeh et al. (2009 ▶), Muranishi et al. (2005 ▶). For complexes of 2,2′-biquinoline, see: Bowmaker et al. (2005 ▶); Butcher & Sinn (1977 ▶); Kou et al. (2008 ▶); Moreno et al. (2007 ▶); Okabe & Muranishi (2005 ▶); Rahimi et al. (2009 ▶); Yoshikawa et al. (2003 ▶); Zhou & Ng (2006 ▶).

Experimental

Crystal data

[ZnBr2(C18H12N2)] M = 481.49 Monoclinic, a = 7.9188 (16) Å b = 12.351 (3) Å c = 17.385 (4) Å β = 103.01 (3)° V = 1656.7 (7) Å3 Z = 4 Mo Kα radiation μ = 6.31 mm−1 T = 298 K 0.20 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.380, T max = 0.530 13476 measured reflections 4471 independent reflections 2968 reflections with I > 2σ(I) R int = 0.098

Refinement

R[F 2 > 2σ(F 2)] = 0.070 wR(F 2) = 0.150 S = 1.15 4471 reflections 208 parameters H-atom parameters constrained Δρmax = 1.14 e Å−3 Δρmin = −0.69 e Å−3 Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810047434/jj2062sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047434/jj2062Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[ZnBr2(C18H12N2)]F(000) = 936
Mr = 481.49Dx = 1.930 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 434 reflections
a = 7.9188 (16) Åθ = 2.0–29.3°
b = 12.351 (3) ŵ = 6.31 mm−1
c = 17.385 (4) ÅT = 298 K
β = 103.01 (3)°Block, colorless
V = 1656.7 (7) Å30.20 × 0.13 × 0.10 mm
Z = 4
Bruker SMART CCD area-detector diffractometer4471 independent reflections
Radiation source: fine-focus sealed tube2968 reflections with I > 2σ(I)
graphiteRint = 0.098
θ and ω scansθmax = 29.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)h = −9→10
Tmin = 0.380, Tmax = 0.530k = −16→16
13476 measured reflectionsl = −23→23
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H-atom parameters constrained
S = 1.15w = 1/[σ2(Fo2) + (0.0538P)2 + 1.2857P] where P = (Fo2 + 2Fc2)/3
4471 reflections(Δ/σ)max = 0.007
208 parametersΔρmax = 1.14 e Å−3
0 restraintsΔρmin = −0.69 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
C10.7304 (8)0.5440 (4)0.0324 (4)0.0354 (13)
C20.8156 (9)0.4877 (5)0.1012 (4)0.0434 (14)
H20.81580.51520.15100.052*
C30.8975 (9)0.3922 (5)0.0933 (5)0.0518 (18)
H30.95390.35470.13820.062*
C40.8974 (10)0.3501 (5)0.0183 (5)0.0529 (18)
H40.95410.28510.01420.063*
C50.8161 (10)0.4024 (5)−0.0483 (5)0.0488 (17)
H50.81610.3728−0.09750.059*
C60.7312 (8)0.5020 (5)−0.0430 (4)0.0386 (13)
C70.6441 (9)0.5609 (5)−0.1093 (4)0.0428 (15)
H70.64300.5354−0.15980.051*
C80.5609 (9)0.6557 (5)−0.1000 (3)0.0424 (15)
H80.50210.6947−0.14360.051*
C90.5666 (8)0.6924 (5)−0.0231 (3)0.0317 (11)
C100.4705 (8)0.7925 (4)−0.0082 (3)0.0313 (12)
C110.3551 (8)0.8467 (5)−0.0691 (4)0.0383 (13)
H110.33840.8227−0.12100.046*
C120.2681 (8)0.9347 (5)−0.0514 (4)0.0409 (14)
H120.19210.9716−0.09150.049*
C130.2924 (8)0.9702 (5)0.0272 (4)0.0387 (13)
C140.2045 (10)1.0612 (5)0.0494 (5)0.0489 (17)
H140.12581.09950.01130.059*
C150.2351 (11)1.0923 (6)0.1259 (5)0.058 (2)
H150.17521.15100.14010.070*
C160.3560 (12)1.0371 (6)0.1841 (5)0.0576 (19)
H160.37771.06100.23610.069*
C170.4432 (10)0.9479 (6)0.1651 (4)0.0495 (17)
H170.52230.91100.20390.059*
C180.4100 (8)0.9135 (5)0.0853 (3)0.0369 (13)
N10.6500 (7)0.6402 (4)0.0408 (3)0.0312 (10)
N20.4991 (7)0.8251 (4)0.0668 (3)0.0320 (10)
Zn10.67435 (10)0.73002 (6)0.14281 (4)0.03680 (19)
Br10.95564 (10)0.80280 (6)0.17474 (5)0.0561 (2)
Br20.55785 (11)0.65496 (6)0.24275 (4)0.0554 (2)
U11U22U33U12U13U23
C10.039 (3)0.029 (3)0.041 (3)−0.006 (2)0.014 (3)0.000 (2)
C20.043 (4)0.044 (3)0.044 (3)0.001 (3)0.010 (3)0.007 (3)
C30.042 (4)0.039 (3)0.074 (5)0.005 (3)0.011 (4)0.013 (3)
C40.045 (4)0.031 (3)0.086 (6)0.001 (3)0.019 (4)−0.007 (3)
C50.053 (4)0.039 (3)0.059 (4)−0.008 (3)0.022 (4)−0.016 (3)
C60.039 (3)0.037 (3)0.042 (3)−0.008 (3)0.015 (3)−0.008 (3)
C70.055 (4)0.039 (3)0.035 (3)−0.011 (3)0.011 (3)−0.016 (3)
C80.051 (4)0.046 (3)0.027 (3)−0.011 (3)0.003 (3)−0.003 (3)
C90.035 (3)0.032 (3)0.026 (2)−0.010 (2)0.003 (2)−0.003 (2)
C100.035 (3)0.031 (3)0.025 (2)−0.006 (2)0.001 (2)0.001 (2)
C110.040 (3)0.040 (3)0.030 (3)−0.007 (3)−0.002 (2)0.005 (2)
C120.037 (3)0.039 (3)0.042 (3)0.001 (3)0.000 (3)0.010 (3)
C130.034 (3)0.037 (3)0.044 (3)−0.002 (2)0.008 (3)0.003 (3)
C140.050 (4)0.035 (3)0.066 (5)0.004 (3)0.022 (4)0.004 (3)
C150.063 (5)0.052 (4)0.071 (5)0.009 (4)0.039 (4)−0.001 (4)
C160.074 (5)0.058 (4)0.046 (4)0.010 (4)0.025 (4)−0.011 (3)
C170.065 (5)0.052 (4)0.034 (3)0.003 (3)0.015 (3)−0.002 (3)
C180.046 (4)0.030 (3)0.035 (3)−0.005 (2)0.011 (3)0.001 (2)
N10.038 (3)0.028 (2)0.027 (2)−0.0014 (19)0.0052 (19)−0.0017 (18)
N20.040 (3)0.030 (2)0.026 (2)0.002 (2)0.0074 (19)0.0012 (18)
Zn10.0467 (4)0.0377 (3)0.0234 (3)0.0022 (3)0.0023 (3)0.0002 (3)
Br10.0502 (4)0.0611 (4)0.0508 (4)−0.0085 (3)−0.0019 (3)−0.0033 (3)
Br20.0760 (5)0.0629 (4)0.0263 (3)−0.0154 (4)0.0095 (3)0.0018 (3)
C1—N11.371 (7)C11—C121.359 (9)
C1—C61.412 (8)C11—H110.9300
C1—C21.416 (9)C12—C131.407 (9)
C2—C31.368 (10)C12—H120.9300
C2—H20.9300C13—C181.399 (9)
C3—C41.404 (11)C13—C141.420 (9)
C3—H30.9300C14—C151.353 (11)
C4—C51.355 (11)C14—H140.9300
C4—H40.9300C15—C161.403 (12)
C5—C61.415 (9)C15—H150.9300
C5—H50.9300C16—C171.379 (10)
C6—C71.405 (9)C16—H160.9300
C7—C81.371 (10)C17—C181.417 (9)
C7—H70.9300C17—H170.9300
C8—C91.403 (8)C18—N21.376 (8)
C8—H80.9300N1—Zn12.063 (4)
C9—N11.325 (7)N2—Zn12.056 (5)
C9—C101.504 (8)Zn1—Br22.3348 (11)
C10—N21.334 (7)Zn1—Br12.3498 (12)
C10—C111.404 (8)
N1—C1—C6121.1 (6)C11—C12—C13120.2 (6)
N1—C1—C2118.8 (6)C11—C12—H12119.9
C6—C1—C2120.1 (6)C13—C12—H12119.9
C3—C2—C1119.1 (7)C18—C13—C12118.0 (6)
C3—C2—H2120.4C18—C13—C14119.2 (6)
C1—C2—H2120.4C12—C13—C14122.9 (6)
C2—C3—C4120.7 (7)C15—C14—C13120.1 (7)
C2—C3—H3119.6C15—C14—H14119.9
C4—C3—H3119.6C13—C14—H14119.9
C5—C4—C3121.2 (6)C14—C15—C16120.8 (7)
C5—C4—H4119.4C14—C15—H15119.6
C3—C4—H4119.4C16—C15—H15119.6
C4—C5—C6120.1 (7)C17—C16—C15120.9 (7)
C4—C5—H5120.0C17—C16—H16119.6
C6—C5—H5120.0C15—C16—H16119.6
C7—C6—C1117.9 (5)C16—C17—C18118.8 (7)
C7—C6—C5123.3 (6)C16—C17—H17120.6
C1—C6—C5118.8 (6)C18—C17—H17120.6
C8—C7—C6120.3 (6)N2—C18—C13121.4 (5)
C8—C7—H7119.8N2—C18—C17118.3 (6)
C6—C7—H7119.8C13—C18—C17120.2 (6)
C7—C8—C9118.4 (6)C9—N1—C1119.3 (5)
C7—C8—H8120.8C9—N1—Zn1113.0 (4)
C9—C8—H8120.8C1—N1—Zn1127.0 (4)
N1—C9—C8123.0 (6)C10—N2—C18119.0 (5)
N1—C9—C10115.6 (5)C10—N2—Zn1113.4 (4)
C8—C9—C10121.4 (5)C18—N2—Zn1127.6 (4)
N2—C10—C11122.1 (5)N2—Zn1—N180.56 (18)
N2—C10—C9115.8 (5)N2—Zn1—Br2112.49 (14)
C11—C10—C9122.0 (5)N1—Zn1—Br2116.75 (13)
C12—C11—C10119.2 (6)N2—Zn1—Br1113.58 (14)
C12—C11—H11120.4N1—Zn1—Br1107.98 (15)
C10—C11—H11120.4Br2—Zn1—Br1119.24 (4)
N1—C1—C2—C3−179.4 (6)C12—C13—C18—C17178.1 (6)
C6—C1—C2—C3−0.3 (9)C14—C13—C18—C17−1.2 (9)
C1—C2—C3—C4−0.1 (10)C16—C17—C18—N2179.3 (6)
C2—C3—C4—C5−0.2 (11)C16—C17—C18—C130.8 (10)
C3—C4—C5—C60.8 (11)C8—C9—N1—C1−2.2 (9)
N1—C1—C6—C7−1.2 (9)C10—C9—N1—C1175.3 (5)
C2—C1—C6—C7179.8 (6)C8—C9—N1—Zn1168.5 (5)
N1—C1—C6—C5180.0 (6)C10—C9—N1—Zn1−13.9 (6)
C2—C1—C6—C50.9 (9)C6—C1—N1—C92.4 (8)
C4—C5—C6—C7−179.9 (7)C2—C1—N1—C9−178.5 (6)
C4—C5—C6—C1−1.2 (10)C6—C1—N1—Zn1−166.9 (4)
C1—C6—C7—C8−0.4 (9)C2—C1—N1—Zn112.2 (8)
C5—C6—C7—C8178.4 (6)C11—C10—N2—C181.3 (8)
C6—C7—C8—C90.6 (9)C9—C10—N2—C18−177.3 (5)
C7—C8—C9—N10.7 (9)C11—C10—N2—Zn1180.0 (4)
C7—C8—C9—C10−176.7 (6)C9—C10—N2—Zn11.4 (6)
N1—C9—C10—N28.6 (7)C13—C18—N2—C10−0.8 (8)
C8—C9—C10—N2−173.8 (5)C17—C18—N2—C10−179.3 (6)
N1—C9—C10—C11−170.0 (5)C13—C18—N2—Zn1−179.3 (4)
C8—C9—C10—C117.6 (9)C17—C18—N2—Zn12.3 (8)
N2—C10—C11—C12−0.6 (9)C10—N2—Zn1—N1−6.6 (4)
C9—C10—C11—C12177.9 (5)C18—N2—Zn1—N1171.8 (5)
C10—C11—C12—C13−0.6 (9)C10—N2—Zn1—Br2−121.8 (4)
C11—C12—C13—C181.1 (9)C18—N2—Zn1—Br256.7 (5)
C11—C12—C13—C14−179.6 (6)C10—N2—Zn1—Br199.0 (4)
C18—C13—C14—C150.2 (10)C18—N2—Zn1—Br1−82.6 (5)
C12—C13—C14—C15−179.1 (7)C9—N1—Zn1—N211.4 (4)
C13—C14—C15—C161.3 (12)C1—N1—Zn1—N2−178.7 (5)
C14—C15—C16—C17−1.8 (13)C9—N1—Zn1—Br2121.9 (4)
C15—C16—C17—C180.7 (12)C1—N1—Zn1—Br2−68.2 (5)
C12—C13—C18—N2−0.4 (9)C9—N1—Zn1—Br1−100.4 (4)
C14—C13—C18—N2−179.7 (5)C1—N1—Zn1—Br169.4 (5)
D—H···AD—HH···AD···AD—H···A
C11—H11···Br2i0.932.873.574 (7)133
Cg1Cg43.775 (4)i
Cg2Cg23.748 (4)i
Cg2Cg43.735 (4)i
Cg3Cg33.538 (4)ii
Cg3Cg53.678 (4)ii
Cg4Cg43.513 (4)iii
N1—Zn12.063 (4)
N2—Zn12.056 (5)
Zn1—Br22.3348 (11)
Zn1—Br12.3498 (12)
N2—Zn1—N180.56 (18)
N2—Zn1—Br2112.49 (14)
N1—Zn1—Br2116.75 (13)
N2—Zn1—Br1113.58 (14)
N1—Zn1—Br1107.98 (15)
Br2—Zn1—Br1119.24 (4)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C11—H11⋯Br2i0.932.873.574 (7)133

Symmetry code: (i) .

  5 in total

1.  (2,2'-Biquinoline-kappa(2)N,N')dichloropalladium(II), -copper(II) and -zinc(II).

Authors:  Yasunori Muranishi; Yue Wang; Mamiko Odoko; Nobuo Okabe
Journal:  Acta Crystallogr C       Date:  2005-05-20       Impact factor: 1.172

2.  A short history of SHELX.

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

3.  (2,2'-Biquinoline-kappa2N,N')bis(nitrato-kappa2O,O')copper(II).

Authors:  Yanko Moreno; Yimmy Salgado; María Teresa Garland; Ricardo Baggio
Journal:  Acta Crystallogr C       Date:  2007-10-13       Impact factor: 1.172

4.  Dibromido(6,6'-dimethyl-2,2'-bipyridine-κN,N')zinc(II).

Authors:  Robabeh Alizadeh; Zeinab Khoshtarkib; Katayoon Chegeni; Amin Ebadi; Vahid Amani
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-07

5.  (2,2'-Biquinoline-κN,N')dichlorido-iron(II).

Authors:  Narjes Rahimi; Nasser Safari; Vahid Amani; Hamid Reza Khavasi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-17
  5 in total

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