Literature DB >> 24098191

Bis(1,10-phenanthroline-κ(2) N,N')(sulfato-κO)copper(II) ethanol monosolvate.

Natthaya Meundaeng1, Timothy J Prior, Apinpus Rujiwatra.   

Abstract

The crystal structure of the title compound, [Cu(SO4)(C12H8N2)2]·C2H5OH, arises from the assembly of the neutral complex [Cu(SO4)(C12H8N2)2] and an ethanol solvent mol-ecule. The Cu(II) ion is five-coordinate, surrounded by two pairs of N atoms from two independent N,N'-chelating 1,10-phenanthroline ligands, and one O atom of monodentate sulfate ligand, in a distorted trigonal-bipyramidal fashion. Spatial orientation of the ligands and the assembly in the solid state are stabilized by the C-H⋯O hydrogen-bonding inter-actions, established between the O atoms (from the sulfate ligand and the ethanol mol-ecule) and the neighbouring 1,10-phenanthroline mol-ecules. There is also an offset face-to-face π-π stacking between the 1,10-phenanthroline ligands. The ethanol solvent mol-ecule is disordered over two orientations in the ratio 0.663 (10):0.337 (10). The crystal examined was subject to racemic twinning and the refined twin fraction was 0.346 (19).

Entities:  

Year:  2013        PMID： 24098191      PMCID： PMC3790369          DOI： 10.1107/S1600536813026093

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


Related literature

Zhong has published many similar compounds with different solvent systems, see, for example: Zhong (2011a ▶,b ▶, 2012 ▶); Zhong & Cao (2013 ▶). For a similar centrosymmetric compound featuring 2,2′-bi­pyridine and bidentate sulfate, see: Wojciechowska et al. (2011 ▶). For similar compounds of different first-row transition metals, see, for example: Zhu et al. (2006 ▶); Zhong et al. (2009 ▶).

Experimental

Crystal data

[Cu(SO4)(C12H8N2)2]·C2H6O M = 564.06 Monoclinic, a = 17.5488 (14) Å b = 11.9360 (11) Å c = 13.0663 (9) Å β = 120.664 (5)° V = 2354.2 (3) Å3 Z = 4 Mo Kα radiation μ = 1.06 mm−1 T = 150 K 0.32 × 0.24 × 0.12 mm

Data collection

Stoe IPDS2 diffractometer Absorption correction: numerical (X-AREA; Stoe & Cie, 2002 ▶) T min = 0.727, T max = 0.883 10087 measured reflections 5771 independent reflections 4259 reflections with I > 2σ(I) R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.058 wR(F 2) = 0.160 S = 1.01 5771 reflections 331 parameters 8 restraints H-atom parameters constrained Δρmax = 1.02 e Å−3 Δρmin = −1.09 e Å−3 Absolute structure: Flack (1983 ▶), 2594 Friedel pairs Absolute structure parameter: 0.346 (19) Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶) and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813026093/gg2128sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813026093/gg2128Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Cu(SO4)(C12H8N2)2]·C2H6OF(000) = 1156
Mr = 564.06Dx = 1.591 Mg m−3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 11381 reflections
a = 17.5488 (14) Åθ = 1.8–29.5°
b = 11.9360 (11) ŵ = 1.06 mm−1
c = 13.0663 (9) ÅT = 150 K
β = 120.664 (5)°Block, blue
V = 2354.2 (3) Å30.32 × 0.24 × 0.12 mm
Z = 4
Stoe IPDS2 diffractometer5771 independent reflections
Radiation source: fine-focus sealed tube4259 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
Detector resolution: 6.67 pixels mm-1θmax = 29.2°, θmin = 2.2°
ω scansh = −24→23
Absorption correction: numerical (X-AREA; Stoe & Cie, 2002)k = −15→16
Tmin = 0.727, Tmax = 0.883l = −17→17
10087 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.160w = 1/[σ2(Fo2) + (0.0966P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
5771 reflectionsΔρmax = 1.02 e Å−3
331 parametersΔρmin = −1.09 e Å−3
8 restraintsAbsolute structure: Flack (1983), 2594 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.346 (19)
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)
N10.9825 (4)0.1792 (4)0.0032 (4)0.0321 (12)
C110.9177 (5)0.2042 (4)0.1237 (6)0.0314 (14)
C90.9264 (5)0.2899 (5)0.3232 (7)0.0358 (16)
H90.93170.31890.39420.043*
C80.8537 (6)0.2293 (5)0.2455 (7)0.0388 (16)
H80.80730.21790.26160.047*
C120.9124 (4)0.1580 (5)0.0166 (5)0.0270 (12)
C70.8467 (5)0.1836 (5)0.1419 (6)0.0322 (13)
C10.9812 (5)0.1396 (6)−0.0927 (6)0.0398 (15)
H11.03030.1539−0.10280.048*
C40.8389 (5)0.0977 (5)−0.0645 (6)0.0341 (14)
C60.7713 (5)0.1197 (6)0.0568 (6)0.0363 (14)
H60.72400.10530.07050.044*
C50.7675 (5)0.0797 (5)−0.0437 (6)0.0369 (15)
H50.71660.0394−0.10040.044*
C20.9085 (6)0.0763 (5)−0.1810 (6)0.0437 (19)
H20.90910.0477−0.24840.052*
C100.9946 (5)0.3089 (5)0.2959 (6)0.0346 (14)
H101.04480.35260.34830.042*
C30.8385 (5)0.0578 (5)−0.1665 (5)0.0358 (14)
H30.78860.0176−0.22540.043*
N41.1718 (4)0.1823 (4)0.2833 (4)0.0291 (11)
N31.1675 (4)0.2753 (4)0.0952 (5)0.0289 (11)
C281.3163 (5)0.0529 (6)0.4483 (6)0.0386 (14)
H281.36360.00720.50430.046*
C271.3163 (5)0.0950 (5)0.3475 (6)0.0324 (14)
C221.2237 (6)0.3009 (6)−0.0345 (6)0.0389 (16)
H221.21570.3323−0.10610.047*
C211.1627 (5)0.3212 (6)−0.0013 (6)0.0382 (15)
H211.11470.3701−0.04890.046*
C301.1765 (5)0.1415 (5)0.3818 (6)0.0351 (14)
H301.12910.15670.39510.042*
C241.3057 (4)0.1865 (5)0.1399 (6)0.0313 (13)
C291.2464 (5)0.0790 (6)0.4645 (6)0.0386 (16)
H291.24690.05330.53360.046*
C231.2969 (6)0.2347 (6)0.0355 (6)0.0367 (15)
H231.34040.22190.01400.044*
O31.0467 (3)0.4360 (3)0.0884 (3)0.0413 (10)
O40.9925 (3)0.6192 (4)0.0848 (4)0.0398 (10)
C321.2395 (5)0.2082 (5)0.1656 (6)0.0298 (13)
C311.2409 (4)0.1608 (5)0.2672 (5)0.0278 (12)
C261.3840 (5)0.0775 (6)0.3205 (6)0.0377 (15)
H261.43380.03370.37370.045*
C251.3812 (5)0.1204 (6)0.2219 (6)0.0383 (14)
H251.42820.10690.20750.046*
Cu11.07989 (4)0.28399 (4)0.14929 (5)0.03031 (16)
S21.06669 (9)0.54426 (10)0.15762 (10)0.0283 (3)
N20.9884 (4)0.2662 (4)0.1978 (5)0.0306 (12)
O11.0717 (3)0.5217 (3)0.2709 (3)0.0329 (8)
O21.1491 (3)0.5917 (4)0.1765 (4)0.0494 (13)
C41A1.0959 (9)0.8927 (10)0.1088 (12)0.059 (3)*0.695 (15)
H41A1.07570.94780.04340.071*0.695 (15)
H41B1.14970.92560.17680.071*0.695 (15)
C42A1.0326 (8)0.8986 (9)0.1425 (11)0.050 (2)*0.695 (15)
H42A1.04910.96410.19620.060*0.695 (15)
H42B0.97630.91860.06960.060*0.695 (15)
C41B1.132 (2)0.890 (2)0.158 (3)0.059 (3)*0.305 (15)
H41C1.11780.96320.11640.071*0.305 (15)
H41D1.19540.89230.21920.071*0.305 (15)
C42B1.0858 (15)0.8890 (19)0.221 (2)0.050 (2)*0.305 (15)
H42C1.13050.87180.30440.060*0.305 (15)
H42D1.06630.96710.21970.060*0.305 (15)
O411.1240 (5)0.8127 (6)0.0766 (7)0.0523 (15)*0.663 (10)
O421.0135 (10)0.8216 (12)0.1916 (14)0.0523 (15)*0.337 (10)
U11U22U33U12U13U23
N10.044 (3)0.028 (3)0.030 (3)0.001 (2)0.023 (3)0.001 (2)
C110.048 (4)0.017 (3)0.027 (3)0.001 (3)0.018 (3)−0.002 (2)
C90.049 (4)0.031 (3)0.035 (4)−0.004 (3)0.027 (4)−0.003 (2)
C80.052 (4)0.032 (3)0.048 (4)0.006 (3)0.037 (4)0.007 (3)
C120.034 (3)0.023 (3)0.020 (2)0.002 (2)0.011 (3)0.001 (2)
C70.042 (4)0.024 (3)0.032 (3)0.008 (3)0.021 (3)0.008 (2)
C10.055 (4)0.037 (4)0.030 (3)0.003 (3)0.024 (3)−0.001 (3)
C40.044 (4)0.029 (3)0.027 (3)−0.001 (3)0.017 (3)0.003 (2)
C60.038 (4)0.036 (3)0.036 (3)−0.002 (3)0.020 (3)0.004 (3)
C50.043 (4)0.030 (3)0.028 (3)−0.003 (3)0.011 (3)0.000 (2)
C20.073 (6)0.031 (3)0.028 (3)−0.008 (3)0.027 (4)−0.009 (3)
C100.048 (4)0.027 (3)0.027 (3)−0.004 (3)0.017 (3)−0.007 (2)
C30.047 (4)0.027 (3)0.021 (3)−0.001 (3)0.008 (3)−0.003 (2)
N40.039 (3)0.024 (2)0.017 (2)0.001 (2)0.009 (2)0.0012 (18)
N30.031 (3)0.029 (3)0.027 (3)0.009 (2)0.015 (3)0.0079 (19)
C280.045 (4)0.034 (3)0.024 (3)0.002 (3)0.007 (3)0.000 (2)
C270.037 (4)0.024 (3)0.024 (3)−0.004 (2)0.006 (3)−0.006 (2)
C220.053 (4)0.042 (4)0.027 (3)0.001 (3)0.024 (4)0.006 (3)
C210.050 (4)0.037 (3)0.038 (4)0.006 (3)0.029 (4)0.009 (3)
C300.048 (4)0.031 (3)0.031 (3)0.008 (3)0.023 (3)0.009 (2)
C240.031 (3)0.031 (3)0.028 (3)0.002 (2)0.012 (3)−0.001 (2)
C290.049 (4)0.039 (4)0.021 (3)0.004 (3)0.013 (3)0.008 (3)
C230.046 (4)0.037 (3)0.030 (3)0.001 (3)0.021 (3)0.000 (3)
O30.069 (3)0.0277 (18)0.030 (2)0.0063 (19)0.027 (2)−0.0005 (15)
O40.041 (3)0.036 (2)0.027 (2)0.0091 (19)0.007 (2)0.0044 (18)
C320.031 (3)0.030 (3)0.023 (3)−0.003 (2)0.010 (3)−0.006 (2)
C310.033 (3)0.023 (3)0.020 (2)0.000 (2)0.008 (3)−0.002 (2)
C260.034 (4)0.040 (4)0.028 (3)0.004 (3)0.008 (3)0.000 (3)
C250.035 (4)0.035 (3)0.037 (3)0.001 (3)0.012 (3)−0.004 (3)
Cu10.0389 (3)0.0257 (2)0.0295 (3)0.0021 (4)0.0197 (3)0.0019 (3)
S20.0318 (8)0.0280 (5)0.0221 (6)−0.0002 (6)0.0116 (6)0.0000 (5)
N20.040 (3)0.029 (3)0.027 (3)−0.001 (2)0.020 (3)−0.0030 (19)
O10.038 (2)0.0352 (18)0.0220 (17)0.0030 (17)0.0128 (18)0.0037 (15)
O20.034 (3)0.075 (4)0.040 (3)−0.013 (2)0.020 (2)0.002 (2)
N1—C11.329 (7)C22—C211.366 (10)
N1—C121.352 (8)C22—C231.383 (11)
N1—Cu12.191 (6)C22—H220.9500
C11—N21.342 (9)C21—H210.9500
C11—C71.405 (10)C30—C291.370 (10)
C11—C121.462 (8)C30—H300.9500
C9—C81.364 (11)C24—C321.389 (9)
C9—C101.431 (10)C24—C231.415 (9)
C9—H90.9500C24—C251.441 (10)
C8—C71.406 (9)C29—H290.9500
C8—H80.9500C23—H230.9500
C12—C41.382 (10)O3—S21.513 (4)
C7—C61.437 (10)O3—Cu11.947 (4)
C1—C21.424 (11)O4—S21.462 (5)
C1—H10.9500C32—C311.431 (8)
C4—C31.412 (9)C26—C251.363 (10)
C4—C51.429 (10)C26—H260.9500
C6—C51.366 (9)C25—H250.9500
C6—H60.9500Cu1—N22.015 (5)
C5—H50.9500S2—O21.453 (5)
C2—C31.354 (11)S2—O11.463 (3)
C2—H20.9500C41A—O411.242 (11)
C10—N21.331 (8)C41A—C42A1.391 (12)
C10—H100.9500C41A—H41A0.9900
C3—H30.9500C41A—H41B0.9900
N4—C301.340 (7)C42A—O421.260 (13)
N4—C311.356 (8)C42A—H42A0.9900
N4—Cu12.064 (5)C42A—H42B0.9900
N3—C211.337 (8)C41B—O411.360 (17)
N3—C321.378 (9)C41B—C42B1.411 (18)
N3—Cu11.995 (5)C41B—H41C0.9900
C28—C291.382 (10)C41B—H41D0.9900
C28—C271.410 (9)C42B—O421.384 (17)
C28—H280.9500C42B—H42C0.9900
C27—C261.416 (10)C42B—H42D0.9900
C27—C311.433 (9)
C1—N1—C12118.4 (6)C30—C29—C28120.7 (6)
C1—N1—Cu1131.0 (5)C30—C29—H29119.7
C12—N1—Cu1110.5 (4)C28—C29—H29119.7
N2—C11—C7123.2 (6)C22—C23—C24118.5 (6)
N2—C11—C12118.9 (6)C22—C23—H23120.7
C7—C11—C12117.9 (6)C24—C23—H23120.7
C8—C9—C10118.9 (6)S2—O3—Cu1128.5 (2)
C8—C9—H9120.6N3—C32—C24122.9 (6)
C10—C9—H9120.6N3—C32—C31115.2 (5)
C9—C8—C7120.8 (7)C24—C32—C31121.9 (6)
C9—C8—H8119.6N4—C31—C32118.3 (6)
C7—C8—H8119.6N4—C31—C27123.7 (5)
N1—C12—C4123.6 (5)C32—C31—C27118.0 (6)
N1—C12—C11115.8 (6)C25—C26—C27123.4 (7)
C4—C12—C11120.6 (6)C25—C26—H26118.3
C11—C7—C8116.5 (6)C27—C26—H26118.3
C11—C7—C6120.5 (6)C26—C25—C24119.0 (7)
C8—C7—C6123.0 (6)C26—C25—H25120.5
N1—C1—C2122.0 (7)C24—C25—H25120.5
N1—C1—H1119.0O3—Cu1—N391.59 (18)
C2—C1—H1119.0O3—Cu1—N296.1 (2)
C12—C4—C3116.9 (6)N3—Cu1—N2170.74 (16)
C12—C4—C5119.9 (6)O3—Cu1—N4146.72 (19)
C3—C4—C5123.1 (7)N3—Cu1—N481.9 (2)
C5—C6—C7120.3 (6)N2—Cu1—N494.3 (2)
C5—C6—H6119.9O3—Cu1—N1103.76 (18)
C7—C6—H6119.9N3—Cu1—N193.5 (2)
C6—C5—C4120.8 (7)N2—Cu1—N179.7 (2)
C6—C5—H5119.6N4—Cu1—N1109.17 (14)
C4—C5—H5119.6O2—S2—O4110.5 (3)
C3—C2—C1118.4 (6)O2—S2—O1111.1 (3)
C3—C2—H2120.8O4—S2—O1110.2 (2)
C1—C2—H2120.8O2—S2—O3110.0 (3)
N2—C10—C9120.8 (6)O4—S2—O3106.0 (3)
N2—C10—H10119.6O1—S2—O3108.9 (2)
C9—C10—H10119.6C10—N2—C11119.8 (6)
C2—C3—C4120.6 (7)C10—N2—Cu1125.1 (5)
C2—C3—H3119.7C11—N2—Cu1115.0 (4)
C4—C3—H3119.7O41—C41A—C42A131.8 (11)
C30—N4—C31117.3 (6)O41—C41A—H41A104.3
C30—N4—Cu1131.8 (4)C42A—C41A—H41A104.3
C31—N4—Cu1110.7 (4)O41—C41A—H41B104.3
C21—N3—C32117.6 (5)C42A—C41A—H41B104.3
C21—N3—Cu1128.5 (5)H41A—C41A—H41B105.6
C32—N3—Cu1113.8 (4)O42—C42A—C41A126.0 (13)
C29—C28—C27119.0 (6)O42—C42A—H42A105.8
C29—C28—H28120.5C41A—C42A—H42A105.8
C27—C28—H28120.5O42—C42A—H42B105.8
C28—C27—C26125.5 (7)C41A—C42A—H42B105.8
C28—C27—C31116.1 (6)H42A—C42A—H42B106.2
C26—C27—C31118.4 (6)O41—C41B—C42B126 (2)
C21—C22—C23120.4 (6)O41—C41B—H41C105.8
C21—C22—H22119.8C42B—C41B—H41C105.8
C23—C22—H22119.8O41—C41B—H41D105.8
N3—C21—C22122.9 (7)C42B—C41B—H41D105.8
N3—C21—H21118.5H41C—C41B—H41D106.2
C22—C21—H21118.5O42—C42B—C41B124 (2)
N4—C30—C29123.1 (6)O42—C42B—H42C106.3
N4—C30—H30118.4C41B—C42B—H42C106.3
C29—C30—H30118.4O42—C42B—H42D106.3
C32—C24—C23117.6 (6)C41B—C42B—H42D106.3
C32—C24—C25119.2 (6)H42C—C42B—H42D106.4
C23—C24—C25123.1 (6)
D—H···AD—HH···AD···AD—H···A
C3—H3···O2i0.952.483.389 (9)161
C5—H5···O1i0.952.343.263 (9)165
C6—H6···O2ii0.952.353.252 (11)158
C9—H9···O4iii0.952.283.188 (9)161
C10—H10···O10.952.412.973 (8)118
C21—H21···O1iv0.952.443.175 (8)134
C25—H25···O1v0.952.443.285 (11)149
C25—H25···O4v0.952.393.255 (11)151
C26—H26···O3vi0.952.503.200 (8)130
C28—H28···O4vi0.952.463.367 (10)159
C30—H30···O41iii0.952.453.165 (12)132
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C3—H3⋯O2i 0.952.483.389 (9)161
C5—H5⋯O1i 0.952.343.263 (9)165
C6—H6⋯O2ii 0.952.353.252 (11)158
C9—H9⋯O4iii 0.952.283.188 (9)161
C10—H10⋯O10.952.412.973 (8)118
C21—H21⋯O1iv 0.952.443.175 (8)134
C25—H25⋯O1v 0.952.443.285 (11)149
C25—H25⋯O4v 0.952.393.255 (11)151
C26—H26⋯O3vi 0.952.503.200 (8)130
C28—H28⋯O4vi 0.952.463.367 (10)159
C30—H30⋯O41iii 0.952.453.165 (12)132

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

  6 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.  Bis(1,10-phenanthroline-κN,N')(sulfato-κO,O')nickel(II) ethane-1,2-diol solvate.

Authors:  Kai-Long Zhong; Chao Ni; Jian-Mei Wang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-07-11

3.  Bis(1,10-phenanthroline-κN,N')(sulfato-O)copper(II) ethane-1,2-diol monosolvate.

Authors:  Kai-Long Zhong
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-08-11

4.  Bis(1,10-phenanthroline-κ(2) N,N')(sulfato-O)copper(II) butane-2,3-diol monosolvate.

Authors:  Kai-Long Zhong; Guo-Qing Cao
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-12-12

5.  Bis(1,10-phenanthroline-κ(2) N,N')(sulfato-O)copper(II) propane-1,3-diol monosolvate.

Authors:  Kai-Long Zhong
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-11-28

6.  Structure validation in chemical crystallography.

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

1.  Crystal structure of aqua-bis-(hepta-fluoro-butano-ato-κO)(1,10'-phenanthroline-κ(2) N,N')copper(II).

Authors:  Ibrahim Kani
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2016-01-01
  1 in total

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