Literature DB >> 26396867

Crystal structure of [N,N'-bis-(4-methyl-phen-yl)-1,2-di-phenyl-ethane-1,2-di-imine-κ(2) N,N']di-chlorido-palladium(II) methanol monosolvate.

Alfredo Peñaloza1, Frank R Fronczek2, Ralph Isovitsch1.   

Abstract

The title compound, [PdCl2(C28H24N2)]·CH3OH, was pre-pared from the reaction of PdCl2(DMSO)2 (DMSO is di-methyl sulfoxide) and N,N'-bis-(4-methyl-phen-yl)-1,2-di-phenyl-ethane-1,2-di-imine in methanol. The chelating di-imine core of the title compound deviates slightly from planarity, with an N-C-C-N torsion angle of 5.3 (3)°. Delocalization in the di-imine core is indicated by N-C and C-C bonds that are, respectively, longer and shorter than those found in related nonchelating di-imines. The distorted square-planar coordination environment around the Pd(II) atom is manifested as bond angles that are smaller and larger than 90°, and palladacycle torsion angles of -173.22 (16) and 167.06 (16)°. These deviations are attributed to the small bite angle of 79.13 (8)° of the di-imine chelate. The crystal packing exhibits weak inter-molecular hydrogen-bonding inter-actions involving aromatic H atoms, Cl atoms and inter-calated methanol solvent mol-ecules, defining layers parallel to (010).

Entities:  

Keywords:  crystal structure; palladium(II) di­chlorido di­imine complex; polymerization catalyst

Year:  2015        PMID： 26396867      PMCID： PMC4555432          DOI： 10.1107/S2056989015014851

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


Related literature

Palladium(II) diimiine complexes have been widely used as polymerization catalysts for α-olefins (Johnson et al., 1995 ▸; Popeney & Guan, 2005 ▸) and are prepared easily by the reaction of PdCl2(DMSO)2 with the di­imine of choice (Kubota et al., 2013 ▸; Ettedgui & Neumann, 2009 ▸; Price et al., 1972 ▸). For structural information about related palladium(II) di­imine complexes, see: Kubota et al. (2013 ▸); Comerlato et al. (2001 ▸); Dyakonenko et al. (2015 ▸). For structures of other di­imines, see: Wang et al. (2012 ▸); Zhao et al. (2015 ▸).

Experimental

Crystal data

[PdCl2(C28H24N2)]·CH4O M = 597.83 Triclinic, a = 8.8213 (3) Å b = 12.3364 (3) Å c = 12.7697 (4) Å α = 108.992 (2)° β = 93.900 (3)° γ = 92.457 (3)° V = 1307.83 (7) Å3 Z = 2 Mo Kα radiation μ = 0.94 mm−1 T = 90 K 0.18 × 0.10 × 0.06 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2014 ▸) T min = 0.831, T max = 0.946 12258 measured reflections 5965 independent reflections 5026 reflections with I > 2σ(I) R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.031 wR(F 2) = 0.066 S = 1.02 5965 reflections 322 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.57 e Å−3 Δρmin = −0.64 e Å−3

Data collection: APEX2 (Bruker, 2014 ▸); cell refinement: SAINT (Bruker, 2014 ▸); data reduction: SAINT; 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, 2012 ▸); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015014851/wm5193sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015014851/wm5193Isup2.hkl Supporting information file. DOI: 10.1107/S2056989015014851/wm5193sup3.pdf Click here for additional data file. . DOI: 10.1107/S2056989015014851/wm5193fig1.tif The mol­ecular components of the title compound. Displacement ellipsoids are represented at the 50% probability level. Click here for additional data file. . DOI: 10.1107/S2056989015014851/wm5193fig2.tif Crystal packing in the title compound, with inter­molecular hydrogen bonding emphasized as dashed lines. Click here for additional data file. . DOI: 10.1107/S2056989015014851/wm5193fig3.tif Crystal packing in the title compound as viewed along [100]. CCDC reference: 1417572 Additional supporting information: crystallographic information; 3D view; checkCIF report
[PdCl2(C28H24N2)]·CH4OZ = 2
Mr = 597.83F(000) = 608
Triclinic, P1Dx = 1.518 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8213 (3) ÅCell parameters from 4900 reflections
b = 12.3364 (3) Åθ = 2.8–27.5°
c = 12.7697 (4) ŵ = 0.94 mm−1
α = 108.992 (2)°T = 90 K
β = 93.900 (3)°Plate, orange
γ = 92.457 (3)°0.18 × 0.10 × 0.06 mm
V = 1307.83 (7) Å3
Bruker Kappa APEXII DUO CCD diffractometer5965 independent reflections
Radiation source: fine-focus sealed tube5026 reflections with I > 2σ(I)
TRIUMPH curved graphite monochromatorRint = 0.032
φ and ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2014)h = −11→11
Tmin = 0.831, Tmax = 0.946k = −16→16
12258 measured reflectionsl = −16→16
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0243P)2 + 0.2447P] where P = (Fo2 + 2Fc2)/3
5965 reflections(Δ/σ)max = 0.002
322 parametersΔρmax = 0.57 e Å−3
1 restraintΔρmin = −0.64 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
Pd10.72678 (2)0.502582 (15)0.508729 (15)0.00896 (6)
Cl10.66581 (7)0.51705 (5)0.33726 (5)0.01389 (13)
Cl20.78558 (7)0.31784 (5)0.42450 (5)0.01609 (14)
N10.7550 (2)0.49790 (16)0.66557 (16)0.0092 (4)
N20.6911 (2)0.66555 (16)0.59660 (16)0.0102 (4)
C10.7157 (3)0.5882 (2)0.7421 (2)0.0109 (5)
C20.6855 (3)0.6871 (2)0.7029 (2)0.0114 (5)
C30.8034 (3)0.39982 (19)0.69323 (19)0.0110 (5)
C40.9500 (3)0.3682 (2)0.67176 (19)0.0125 (5)
H41.01220.40740.63570.015*
C51.0047 (3)0.2789 (2)0.7035 (2)0.0151 (5)
H51.10580.25800.69000.018*
C60.9146 (3)0.2192 (2)0.7545 (2)0.0150 (5)
C70.7650 (3)0.2482 (2)0.7692 (2)0.0163 (6)
H70.70020.20540.80020.020*
C80.7082 (3)0.3385 (2)0.7394 (2)0.0130 (5)
H80.60600.35780.75050.016*
C90.9798 (3)0.1291 (2)0.7979 (2)0.0226 (6)
H9A1.06740.09850.75730.034*
H9B0.90180.06670.78740.034*
H9C1.01260.16390.87730.034*
C100.7048 (3)0.59987 (19)0.8604 (2)0.0112 (5)
C110.8257 (3)0.5791 (2)0.9252 (2)0.0142 (5)
H110.91850.55600.89370.017*
C120.8109 (3)0.5920 (2)1.0360 (2)0.0186 (6)
H120.89430.57891.08050.022*
C130.6756 (3)0.6238 (2)1.0820 (2)0.0212 (6)
H130.66580.63181.15770.025*
C140.5547 (3)0.6441 (2)1.0180 (2)0.0184 (6)
H140.46160.66541.04960.022*
C150.5689 (3)0.6334 (2)0.9075 (2)0.0155 (5)
H150.48620.64880.86410.019*
C160.6638 (3)0.8028 (2)0.78122 (19)0.0117 (5)
C170.5369 (3)0.8595 (2)0.7631 (2)0.0158 (5)
H170.46300.82280.70290.019*
C180.5185 (3)0.9697 (2)0.8332 (2)0.0192 (6)
H180.43161.00840.82100.023*
C190.6264 (3)1.0236 (2)0.9210 (2)0.0211 (6)
H190.61451.09970.96810.025*
C200.7514 (3)0.9665 (2)0.9400 (2)0.0192 (6)
H200.82441.00311.00100.023*
C210.7709 (3)0.8564 (2)0.8709 (2)0.0155 (5)
H210.85680.81750.88440.019*
C220.6995 (3)0.75880 (19)0.55233 (19)0.0107 (5)
C230.5828 (3)0.7719 (2)0.4801 (2)0.0130 (5)
H230.49600.71880.45810.016*
C240.5944 (3)0.8638 (2)0.4402 (2)0.0141 (5)
H240.51460.87340.39080.017*
C250.7211 (3)0.9422 (2)0.4715 (2)0.0136 (5)
C260.8371 (3)0.9256 (2)0.5424 (2)0.0149 (5)
H260.92430.97830.56400.018*
C270.8288 (3)0.8339 (2)0.5825 (2)0.0135 (5)
H270.91010.82270.62980.016*
C280.7325 (3)1.0438 (2)0.4304 (2)0.0200 (6)
H28A0.80041.02800.37040.030*
H28B0.77341.11220.49170.030*
H28C0.63111.05720.40260.030*
O10.9588 (2)0.31675 (18)0.21549 (16)0.0275 (5)
H10H0.916 (4)0.333 (3)0.274 (2)0.041*
C290.8406 (3)0.2883 (3)0.1302 (2)0.0322 (8)
H29A0.76350.23620.14410.048*
H29B0.88150.25050.05890.048*
H29C0.79420.35840.12810.048*
U11U22U33U12U13U23
Pd10.01082 (10)0.00890 (9)0.00697 (10)−0.00045 (7)0.00080 (7)0.00251 (7)
Cl10.0166 (3)0.0163 (3)0.0086 (3)0.0014 (2)−0.0004 (2)0.0042 (2)
Cl20.0252 (4)0.0101 (3)0.0123 (3)0.0019 (2)0.0020 (3)0.0027 (2)
N10.0083 (10)0.0103 (10)0.0096 (10)−0.0003 (8)0.0001 (8)0.0045 (8)
N20.0105 (10)0.0094 (10)0.0110 (10)0.0014 (8)0.0002 (8)0.0037 (8)
C10.0070 (12)0.0140 (12)0.0120 (12)−0.0020 (9)−0.0010 (9)0.0055 (10)
C20.0091 (12)0.0126 (12)0.0123 (12)0.0010 (9)0.0012 (9)0.0037 (10)
C30.0153 (13)0.0085 (11)0.0076 (12)0.0006 (9)−0.0016 (9)0.0010 (10)
C40.0135 (13)0.0141 (12)0.0084 (12)0.0003 (10)0.0008 (10)0.0018 (10)
C50.0147 (13)0.0171 (13)0.0103 (13)0.0046 (10)0.0010 (10)−0.0001 (10)
C60.0247 (15)0.0090 (12)0.0095 (12)0.0046 (10)−0.0028 (10)0.0012 (10)
C70.0227 (15)0.0134 (13)0.0132 (13)−0.0013 (11)0.0033 (11)0.0049 (11)
C80.0138 (13)0.0131 (12)0.0106 (12)−0.0003 (10)0.0001 (10)0.0021 (10)
C90.0314 (16)0.0203 (14)0.0182 (15)0.0105 (12)0.0013 (12)0.0083 (12)
C100.0138 (13)0.0089 (12)0.0107 (12)−0.0005 (9)0.0001 (10)0.0034 (10)
C110.0149 (13)0.0133 (12)0.0146 (13)0.0036 (10)0.0001 (10)0.0051 (10)
C120.0244 (15)0.0172 (14)0.0121 (13)−0.0012 (11)−0.0066 (11)0.0038 (11)
C130.0306 (16)0.0221 (14)0.0113 (13)−0.0031 (12)0.0034 (12)0.0066 (11)
C140.0190 (14)0.0204 (14)0.0150 (14)−0.0001 (11)0.0052 (11)0.0041 (11)
C150.0183 (14)0.0142 (13)0.0142 (13)0.0002 (10)−0.0001 (10)0.0053 (11)
C160.0159 (13)0.0110 (12)0.0087 (12)0.0009 (10)0.0025 (10)0.0036 (10)
C170.0188 (14)0.0179 (13)0.0114 (13)0.0026 (10)0.0016 (10)0.0057 (11)
C180.0222 (15)0.0187 (14)0.0194 (14)0.0086 (11)0.0055 (11)0.0084 (12)
C190.0324 (17)0.0136 (13)0.0165 (14)0.0031 (12)0.0103 (12)0.0023 (11)
C200.0252 (15)0.0165 (13)0.0124 (13)−0.0042 (11)0.0004 (11)0.0010 (11)
C210.0182 (14)0.0166 (13)0.0127 (13)0.0018 (10)0.0011 (10)0.0062 (11)
C220.0162 (13)0.0079 (11)0.0085 (12)0.0031 (9)0.0045 (10)0.0023 (9)
C230.0132 (13)0.0139 (12)0.0105 (12)0.0011 (10)0.0014 (10)0.0021 (10)
C240.0138 (13)0.0173 (13)0.0119 (13)0.0056 (10)0.0008 (10)0.0052 (11)
C250.0179 (13)0.0119 (12)0.0125 (13)0.0044 (10)0.0063 (10)0.0046 (10)
C260.0148 (13)0.0138 (13)0.0170 (14)−0.0003 (10)0.0031 (10)0.0063 (11)
C270.0138 (13)0.0178 (13)0.0093 (12)0.0002 (10)−0.0004 (10)0.0053 (10)
C280.0232 (15)0.0182 (14)0.0243 (15)0.0064 (11)0.0077 (12)0.0129 (12)
O10.0199 (11)0.0366 (12)0.0214 (11)0.0001 (9)0.0066 (9)0.0027 (10)
C290.0231 (17)0.0367 (18)0.0260 (17)−0.0004 (13)0.0067 (13)−0.0050 (14)
Pd1—N22.0086 (19)C14—C151.388 (3)
Pd1—N12.0211 (19)C14—H140.9500
Pd1—Cl22.2807 (6)C15—H150.9500
Pd1—Cl12.2842 (6)C16—C171.390 (4)
N1—C11.299 (3)C16—C211.396 (3)
N1—C31.440 (3)C17—C181.386 (4)
N2—C21.300 (3)C17—H170.9500
N2—C221.439 (3)C18—C191.386 (4)
C1—C101.480 (3)C18—H180.9500
C1—C21.489 (3)C19—C201.383 (4)
C2—C161.481 (3)C19—H190.9500
C3—C41.386 (3)C20—C211.383 (4)
C3—C81.390 (3)C20—H200.9500
C4—C51.386 (3)C21—H210.9500
C4—H40.9500C22—C231.386 (3)
C5—C61.389 (3)C22—C271.387 (3)
C5—H50.9500C23—C241.388 (3)
C6—C71.392 (4)C23—H230.9500
C6—C91.512 (3)C24—C251.392 (3)
C7—C81.390 (3)C24—H240.9500
C7—H70.9500C25—C261.386 (4)
C8—H80.9500C25—C281.511 (3)
C9—H9A0.9800C26—C271.387 (3)
C9—H9B0.9800C26—H260.9500
C9—H9C0.9800C27—H270.9500
C10—C111.389 (3)C28—H28A0.9800
C10—C151.396 (3)C28—H28B0.9800
C11—C121.387 (3)C28—H28C0.9800
C11—H110.9500O1—C291.400 (4)
C12—C131.382 (4)O1—H10H0.831 (17)
C12—H120.9500C29—H29A0.9800
C13—C141.380 (4)C29—H29B0.9800
C13—H130.9500C29—H29C0.9800
N2—Pd1—N179.13 (8)C13—C14—H14119.9
N2—Pd1—Cl2173.82 (6)C15—C14—H14119.9
N1—Pd1—Cl295.67 (6)C14—C15—C10119.9 (2)
N2—Pd1—Cl196.49 (6)C14—C15—H15120.0
N1—Pd1—Cl1172.74 (6)C10—C15—H15120.0
Cl2—Pd1—Cl189.02 (2)C17—C16—C21119.8 (2)
C1—N1—C3120.6 (2)C17—C16—C2119.3 (2)
C1—N1—Pd1115.20 (17)C21—C16—C2120.8 (2)
C3—N1—Pd1124.03 (15)C18—C17—C16119.9 (2)
C2—N2—C22119.9 (2)C18—C17—H17120.1
C2—N2—Pd1115.61 (16)C16—C17—H17120.1
C22—N2—Pd1123.53 (15)C19—C18—C17120.2 (3)
N1—C1—C10125.8 (2)C19—C18—H18119.9
N1—C1—C2114.2 (2)C17—C18—H18119.9
C10—C1—C2120.0 (2)C20—C19—C18119.9 (2)
N2—C2—C16123.2 (2)C20—C19—H19120.1
N2—C2—C1114.7 (2)C18—C19—H19120.1
C16—C2—C1121.9 (2)C19—C20—C21120.5 (3)
C4—C3—C8120.8 (2)C19—C20—H20119.8
C4—C3—N1117.3 (2)C21—C20—H20119.8
C8—C3—N1121.9 (2)C20—C21—C16119.7 (3)
C3—C4—C5119.2 (2)C20—C21—H21120.1
C3—C4—H4120.4C16—C21—H21120.1
C5—C4—H4120.4C23—C22—C27121.0 (2)
C4—C5—C6121.3 (2)C23—C22—N2120.8 (2)
C4—C5—H5119.4C27—C22—N2118.1 (2)
C6—C5—H5119.4C22—C23—C24119.1 (2)
C5—C6—C7118.3 (2)C22—C23—H23120.5
C5—C6—C9120.8 (2)C24—C23—H23120.5
C7—C6—C9120.8 (2)C23—C24—C25121.1 (2)
C8—C7—C6121.4 (2)C23—C24—H24119.5
C8—C7—H7119.3C25—C24—H24119.5
C6—C7—H7119.3C26—C25—C24118.5 (2)
C3—C8—C7118.8 (2)C26—C25—C28120.3 (2)
C3—C8—H8120.6C24—C25—C28121.2 (2)
C7—C8—H8120.6C25—C26—C27121.5 (2)
C6—C9—H9A109.5C25—C26—H26119.2
C6—C9—H9B109.5C27—C26—H26119.2
H9A—C9—H9B109.5C26—C27—C22118.8 (2)
C6—C9—H9C109.5C26—C27—H27120.6
H9A—C9—H9C109.5C22—C27—H27120.6
H9B—C9—H9C109.5C25—C28—H28A109.5
C11—C10—C15119.5 (2)C25—C28—H28B109.5
C11—C10—C1121.9 (2)H28A—C28—H28B109.5
C15—C10—C1118.6 (2)C25—C28—H28C109.5
C12—C11—C10119.9 (2)H28A—C28—H28C109.5
C12—C11—H11120.0H28B—C28—H28C109.5
C10—C11—H11120.0C29—O1—H10H105 (2)
C13—C12—C11120.4 (3)O1—C29—H29A109.5
C13—C12—H12119.8O1—C29—H29B109.5
C11—C12—H12119.8H29A—C29—H29B109.5
C14—C13—C12120.0 (2)O1—C29—H29C109.5
C14—C13—H13120.0H29A—C29—H29C109.5
C12—C13—H13120.0H29B—C29—H29C109.5
C13—C14—C15120.2 (3)
N2—Pd1—N1—C110.15 (16)N1—C1—C10—C15−126.3 (3)
Cl2—Pd1—N1—C1−173.22 (16)C2—C1—C10—C1556.1 (3)
N2—Pd1—N1—C3−174.59 (18)C15—C10—C11—C12−0.2 (3)
Cl2—Pd1—N1—C32.04 (17)C1—C10—C11—C12179.5 (2)
N1—Pd1—N2—C2−7.07 (17)C10—C11—C12—C131.0 (4)
Cl1—Pd1—N2—C2167.06 (16)C11—C12—C13—C14−0.7 (4)
N1—Pd1—N2—C22161.36 (19)C12—C13—C14—C15−0.4 (4)
Cl1—Pd1—N2—C22−24.50 (18)C13—C14—C15—C101.2 (4)
C3—N1—C1—C10−4.4 (3)C11—C10—C15—C14−0.9 (3)
Pd1—N1—C1—C10171.05 (18)C1—C10—C15—C14179.4 (2)
C3—N1—C1—C2173.36 (19)N2—C2—C16—C1756.3 (3)
Pd1—N1—C1—C2−11.2 (2)C1—C2—C16—C17−128.8 (2)
C22—N2—C2—C169.6 (3)N2—C2—C16—C21−122.0 (3)
Pd1—N2—C2—C16178.51 (18)C1—C2—C16—C2152.8 (3)
C22—N2—C2—C1−165.5 (2)C21—C16—C17—C181.0 (3)
Pd1—N2—C2—C13.3 (3)C2—C16—C17—C18−177.4 (2)
N1—C1—C2—N25.3 (3)C16—C17—C18—C190.2 (4)
C10—C1—C2—N2−176.8 (2)C17—C18—C19—C20−1.2 (4)
N1—C1—C2—C16−170.0 (2)C18—C19—C20—C211.0 (4)
C10—C1—C2—C167.9 (3)C19—C20—C21—C160.2 (4)
C1—N1—C3—C4−119.0 (2)C17—C16—C21—C20−1.2 (4)
Pd1—N1—C3—C466.0 (3)C2—C16—C21—C20177.2 (2)
C1—N1—C3—C861.1 (3)C2—N2—C22—C23−115.9 (3)
Pd1—N1—C3—C8−113.9 (2)Pd1—N2—C22—C2376.1 (3)
C8—C3—C4—C5−4.1 (4)C2—N2—C22—C2765.1 (3)
N1—C3—C4—C5176.0 (2)Pd1—N2—C22—C27−102.8 (2)
C3—C4—C5—C61.1 (4)C27—C22—C23—C24−1.9 (4)
C4—C5—C6—C72.6 (4)N2—C22—C23—C24179.2 (2)
C4—C5—C6—C9−174.5 (2)C22—C23—C24—C250.2 (4)
C5—C6—C7—C8−3.5 (4)C23—C24—C25—C260.9 (4)
C9—C6—C7—C8173.6 (2)C23—C24—C25—C28−178.6 (2)
C4—C3—C8—C73.3 (4)C24—C25—C26—C27−0.3 (4)
N1—C3—C8—C7−176.8 (2)C28—C25—C26—C27179.2 (2)
C6—C7—C8—C30.6 (4)C25—C26—C27—C22−1.3 (4)
N1—C1—C10—C1154.0 (3)C23—C22—C27—C262.4 (4)
C2—C1—C10—C11−123.6 (3)N2—C22—C27—C26−178.6 (2)
D—H···AD—HH···AD···AD—H···A
O1—H10H···Cl20.83 (2)2.36 (2)3.161 (2)163 (3)
C17—H17···Cl2i0.952.803.708 (3)161
C21—H21···O1ii0.952.483.275 (3)141
Table 1

Hydrogen-bond geometry (, )

DHA DHHA D A DHA
O1H10HCl20.83(2)2.36(2)3.161(2)163(3)
C17H17Cl2i 0.952.803.708(3)161
C21H21O1ii 0.952.483.275(3)141

Symmetry codes: (i) ; (ii) .

  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.  Phenanthroline decorated by a crown ether as a module for metallorganic-polyoxometalate hybrid catalysts: the Wacker type oxidation of alkenes with nitrous oxide as terminal oxidant.

Authors:  Jessica Ettedgui; Ronny Neumann
Journal:  J Am Chem Soc       Date:  2009-01-14       Impact factor: 15.419

3.  N,N'-Bis(2,6-diethyl-phen-yl)acenaphthyl-ene-1,2-diimine.

Authors:  Li Wang; Xuyang Luo; Bo Gao; Qiaolin Wu; Ying Mu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-12-14
  3 in total

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