Literature DB >> 21587465

Bromidotricarbon-yl[4-iodo-N-(pyridin-2-yl-methyl-idene)aniline-κN,N']rhenium(I).

Saeed Dehghanpour1, Ali Mahmoudi.   

Abstract

In the title compound, [ReBr(C(12)H(9)IN(2))(CO)(3)], the coordination geometry of the Re(I) ion is a distorted fac-ReC(3)BrN(2) octa-hedron, arising from the N,N'-bidentate ligand, a bromide ion and a facial arrangement of three carbonyl ligands. The dihedral angle between the aromatic rings in the 4-iodo-N-(pyridin-2-yl-methyl-idene)aniline ligand is 46.2 (3)°. The bromide ion and its corresponding trans CO mol-ecule are disordered over two sets of sites in a 0.966 (3):0.034 (3) ratio.

Entities:  

Year:  2010        PMID： 21587465      PMCID： PMC2983412          DOI： 10.1107/S1600536810037104

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


Related literature

For the synthesis of the ligand, see: Dehghanpour et al. (2009a ▶). For background to diimine complexes and related structures see: Dehghanpour et al. (2009b ▶, 2010 ▶).

Experimental

Crystal data

[ReBr(C12H9IN2)(CO)3] M = 658.25 Triclinic, a = 8.8850 (4) Å b = 9.0239 (4) Å c = 10.9736 (4) Å α = 75.202 (2)° β = 80.885 (3)° γ = 84.668 (3)° V = 838.64 (6) Å3 Z = 2 Mo Kα radiation μ = 11.48 mm−1 T = 150 K 0.08 × 0.07 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.463, T max = 0.707 9719 measured reflections 3796 independent reflections 3256 reflections with I > 2σ(I) R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.108 S = 1.04 3796 reflections 212 parameters 1 restraint H-atom parameters constrained Δρmax = 2.74 e Å−3 Δρmin = −2.80 e Å−3 Data collection: COLLECT (Nonius, 2002 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810037104/hb5621sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037104/hb5621Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[ReBr(C12H9IN2)(CO)3]Z = 2
Mr = 658.25F(000) = 600
Triclinic, P1Dx = 2.607 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8850 (4) ÅCell parameters from 9719 reflections
b = 9.0239 (4) Åθ = 2.7–27.5°
c = 10.9736 (4) ŵ = 11.48 mm−1
α = 75.202 (2)°T = 150 K
β = 80.885 (3)°Block, red
γ = 84.668 (3)°0.08 × 0.07 × 0.03 mm
V = 838.64 (6) Å3
Nonius KappaCCD diffractometer3796 independent reflections
Radiation source: fine-focus sealed tube3256 reflections with I > 2σ(I)
graphiteRint = 0.059
Detector resolution: 9 pixels mm-1θmax = 27.5°, θmin = 2.7°
φ scans and ω scans with κ offsetsh = −10→11
Absorption correction: multi-scan (SORTAV; Blessing, 1995)k = −11→11
Tmin = 0.463, Tmax = 0.707l = −12→14
9719 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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0591P)2 + 1.7708P] where P = (Fo2 + 2Fc2)/3
3796 reflections(Δ/σ)max = 0.001
212 parametersΔρmax = 2.74 e Å−3
1 restraintΔρmin = −2.80 e Å−3
Experimental. multi-scan from symmetry-related measurements SORTAV (Blessing 1995)
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*/UeqOcc. (<1)
Re10.71427 (3)0.42431 (3)0.25069 (2)0.02270 (11)
I11.35429 (6)−0.18136 (6)0.09158 (5)0.03272 (15)
Br10.77459 (9)0.28546 (8)0.47903 (6)0.0279 (2)0.966 (3)
O10.6470 (7)0.5896 (8)−0.0170 (7)0.0374 (14)
O20.6352 (7)0.7283 (6)0.3297 (6)0.0395 (13)
O31.0434 (6)0.5242 (6)0.1639 (5)0.0387 (13)
N10.4879 (7)0.3344 (6)0.3111 (5)0.0222 (12)
N20.7420 (7)0.1892 (6)0.2274 (5)0.0224 (12)
C10.6686 (12)0.5243 (11)0.0821 (10)0.028 (2)
C20.6644 (8)0.6156 (8)0.2979 (7)0.0293 (16)
C30.9211 (9)0.4851 (8)0.1974 (7)0.0270 (15)
C40.3602 (9)0.4075 (8)0.3539 (7)0.0293 (16)
H4A0.36510.51040.35900.035*
C50.2205 (7)0.3394 (7)0.3913 (6)0.0191 (13)
H5A0.13330.39360.42440.023*
C60.2107 (9)0.1929 (9)0.3795 (7)0.0318 (17)
H6A0.11530.14630.40060.038*
C70.3416 (9)0.1134 (9)0.3365 (7)0.0323 (17)
H7A0.33810.01090.32990.039*
C80.4770 (9)0.1874 (8)0.3036 (6)0.0279 (15)
C90.6197 (8)0.1133 (8)0.2602 (6)0.0258 (15)
H9A0.62340.00920.25590.031*
C100.8834 (8)0.1079 (7)0.1978 (6)0.0217 (14)
C110.9899 (8)0.1744 (8)0.0970 (6)0.0257 (15)
H11A0.97050.27640.04950.031*
C121.1240 (9)0.0943 (9)0.0646 (7)0.0310 (16)
H12A1.19530.1396−0.00620.037*
C131.1535 (8)−0.0534 (8)0.1370 (7)0.0261 (15)
C141.0489 (9)−0.1201 (8)0.2407 (6)0.0274 (15)
H14A1.0700−0.22070.29010.033*
C150.9143 (9)−0.0397 (8)0.2718 (6)0.0269 (15)
H15A0.8431−0.08440.34290.032*
Br1A0.652 (6)0.551 (5)0.040 (3)0.030*0.034 (3)
U11U22U33U12U13U23
Re10.02352 (18)0.01442 (16)0.02889 (18)−0.00057 (11)−0.00101 (12)−0.00477 (11)
I10.0290 (3)0.0314 (3)0.0382 (3)0.0068 (2)−0.0042 (2)−0.0126 (2)
Br10.0331 (4)0.0230 (4)0.0266 (4)0.0010 (3)−0.0037 (3)−0.0056 (3)
O10.038 (3)0.034 (4)0.038 (4)−0.002 (3)−0.002 (3)−0.007 (3)
O20.046 (3)0.021 (3)0.055 (3)0.001 (2)−0.008 (3)−0.015 (2)
O30.027 (3)0.035 (3)0.051 (3)−0.011 (2)−0.001 (3)−0.004 (3)
N10.024 (3)0.019 (3)0.022 (3)0.001 (2)−0.002 (2)−0.003 (2)
N20.031 (3)0.015 (3)0.020 (3)0.004 (2)−0.003 (2)−0.006 (2)
C10.023 (4)0.016 (5)0.047 (6)−0.002 (3)0.000 (5)−0.016 (4)
C20.024 (4)0.026 (4)0.035 (4)0.002 (3)−0.001 (3)−0.004 (3)
C30.028 (4)0.021 (3)0.030 (4)0.002 (3)−0.009 (3)−0.002 (3)
C40.031 (4)0.022 (4)0.034 (4)0.003 (3)−0.005 (3)−0.006 (3)
C50.015 (3)0.022 (3)0.019 (3)0.001 (3)−0.005 (2)−0.003 (2)
C60.031 (4)0.030 (4)0.033 (4)−0.011 (3)−0.004 (3)−0.002 (3)
C70.040 (4)0.024 (4)0.034 (4)−0.005 (3)−0.007 (3)−0.006 (3)
C80.031 (4)0.028 (4)0.026 (3)0.001 (3)−0.004 (3)−0.009 (3)
C90.033 (4)0.017 (3)0.027 (3)−0.006 (3)−0.002 (3)−0.004 (3)
C100.026 (3)0.015 (3)0.024 (3)0.000 (3)−0.002 (3)−0.007 (3)
C110.029 (4)0.018 (3)0.029 (3)0.003 (3)−0.003 (3)−0.005 (3)
C120.032 (4)0.032 (4)0.028 (4)−0.007 (3)0.007 (3)−0.008 (3)
C130.025 (4)0.025 (4)0.031 (4)0.004 (3)0.000 (3)−0.016 (3)
C140.035 (4)0.022 (3)0.025 (3)0.003 (3)−0.008 (3)−0.006 (3)
C150.035 (4)0.023 (3)0.022 (3)−0.005 (3)−0.004 (3)−0.003 (3)
Re1—C21.919 (7)C5—C61.373 (10)
Re1—C31.924 (8)C5—H5A0.9500
Re1—C11.928 (11)C6—C71.391 (11)
Re1—N12.179 (6)C6—H6A0.9500
Re1—N22.188 (5)C7—C81.383 (11)
Re1—Br1A2.43 (3)C7—H7A0.9500
Re1—Br12.6139 (8)C8—C91.447 (10)
I1—C132.096 (7)C9—H9A0.9500
O1—Br1A0.64 (3)C10—C111.383 (9)
O1—C11.133 (13)C10—C151.400 (9)
O2—C21.153 (9)C11—C121.380 (10)
O3—C31.148 (9)C11—H11A0.9500
N1—C41.339 (9)C12—C131.392 (10)
N1—C81.364 (9)C12—H12A0.9500
N2—C91.291 (9)C13—C141.394 (10)
N2—C101.430 (9)C14—C151.381 (10)
C1—Br1A0.50 (3)C14—H14A0.9500
C4—C51.391 (10)C15—H15A0.9500
C4—H4A0.9500
C2—Re1—C388.3 (3)C6—C5—C4119.0 (6)
C2—Re1—C188.8 (4)C6—C5—H5A120.5
C3—Re1—C188.9 (4)C4—C5—H5A120.5
C2—Re1—N196.6 (3)C5—C6—C7119.3 (7)
C3—Re1—N1174.8 (3)C5—C6—H6A120.3
C1—Re1—N192.7 (3)C7—C6—H6A120.3
C2—Re1—N2169.6 (3)C8—C7—C6118.3 (7)
C3—Re1—N299.9 (3)C8—C7—H7A120.8
C1—Re1—N297.5 (3)C6—C7—H7A120.8
N1—Re1—N275.0 (2)N1—C8—C7123.0 (7)
C2—Re1—Br1A88.4 (12)N1—C8—C9114.5 (6)
C3—Re1—Br1A89.8 (12)C7—C8—C9122.4 (7)
C1—Re1—Br1A1.0 (14)N2—C9—C8119.8 (6)
N1—Re1—Br1A91.9 (12)N2—C9—H9A120.1
N2—Re1—Br1A97.8 (12)C8—C9—H9A120.1
C2—Re1—Br191.8 (2)C11—C10—C15119.9 (6)
C3—Re1—Br191.6 (2)C11—C10—N2120.4 (6)
C1—Re1—Br1179.2 (3)C15—C10—N2119.7 (6)
N1—Re1—Br186.79 (14)C12—C11—C10120.8 (6)
N2—Re1—Br181.81 (14)C12—C11—H11A119.6
Br1A—Re1—Br1178.6 (12)C10—C11—H11A119.6
Br1A—O1—C16(5)C11—C12—C13119.2 (6)
C4—N1—C8117.2 (6)C11—C12—H12A120.4
C4—N1—Re1127.3 (5)C13—C12—H12A120.4
C8—N1—Re1115.5 (5)C12—C13—C14120.5 (6)
C9—N2—C10118.1 (6)C12—C13—I1121.0 (5)
C9—N2—Re1115.1 (5)C14—C13—I1118.5 (5)
C10—N2—Re1126.1 (4)C15—C14—C13119.9 (7)
Br1A—C1—O17(7)C15—C14—H14A120.0
Br1A—C1—Re1175 (7)C13—C14—H14A120.0
O1—C1—Re1176.0 (8)C14—C15—C10119.6 (6)
O2—C2—Re1178.0 (7)C14—C15—H15A120.2
O3—C3—Re1178.5 (7)C10—C15—H15A120.2
N1—C4—C5123.0 (7)C1—Br1A—O1167 (10)
N1—C4—H4A118.5C1—Br1A—Re14(6)
C5—C4—H4A118.5O1—Br1A—Re1170 (6)
Table 1

Selected bond lengths (Å)

Re1—C21.919 (7)
Re1—C31.924 (8)
Re1—C11.928 (11)
Re1—N12.179 (6)
Re1—N22.188 (5)
Re1—Br12.6139 (8)
  3 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.  An empirical correction for absorption anisotropy.

Authors:  R H Blessing
Journal:  Acta Crystallogr A       Date:  1995-01-01       Impact factor: 2.290

3.  Structure validation in chemical crystallography.

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

1.  The synthesis and pH-dependent behaviour of Re(CO)3 conjugates with diimine phenolic ligands.

Authors:  Kullapa Chanawanno; James T Engle; Kevin X Le; Richard S Herrick; Christopher J Ziegler
Journal:  Dalton Trans       Date:  2013-08-01       Impact factor: 4.390

2.  The synthesis of biologically relevant conjugates of Re(CO)3 using pyridine-2-carboxyaldehyde.

Authors:  Roshinee Costa; Kullapa Chanawanno; James T Engle; Bertha Baroody; Richard S Herrick; Christopher J Ziegler
Journal:  J Organomet Chem       Date:  2013-06-15       Impact factor: 2.369

3.  Bromidotricarbon-yl[4-chloro-N-(2-pyridyl-methyl-idene)aniline-κN,N']rhenium(I).

Authors:  Mehdi Khalaj; Saeed Dehghanpour; Roghaieh Aleeshah; Ali Mahmoudi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-11-24
  3 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.