Literature DB >> 21753974

Bis(2-amino-6-methyl-pyridinium) trans-diaqua-bis-(pyrazine-2,3-dicarboxyl-ato)cuprate(II) hexa-hydrate.

Hossein Eshtiagh-Hosseini, Azam Hassanpoor, Masoud Mirzaei, Teresa Szymańska-Buzar, Andrzej Kochel.   

Abstract

The title compound, (C(6)H(9)N(2))(2)[Cu(C(6)H(2)N(2)O(4))(2)(H(2)O)(2)]·6H(2)O, was obtained by the reaction of CuCl(2)·2H(2)O with pyrazine-2,3-dicarb-oxy-lic acid (pyzdcH(2)) and 2-amino-6-methyl-pyridine (2a-6mpy) in aqueous solution. The Cu(II) atom is located on an inversion centre and has an overall octa-hedral coordination environment. Two N and two O atoms from (pyzdc)(2-) ligands define the equatorial plane and two water mol-ecules are in axial positions, resulting in a typical tetra-gonally Jahn-Teller-distorted environment. Extensive classical O-H⋯O, O-H⋯N and N-H⋯O and non-classical C-H⋯O hydrogen bonds, as well as π-π stacking inter-actions between aromatic rings of the cations [centroid-centroid distance = 3.58 (9) Å], lead to the formation of a three-dimensional supra-molecular structure.

Entities:  

Year:  2011        PMID： 21753974      PMCID： PMC3100057          DOI： 10.1107/S1600536811008981

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


Related literature

For background to this class of compounds, see: Aghabozorg et al. (2008 ▶, 2010 ▶). For related structures, see: Eshtiagh-Hosseini et al. (2010a ▶,b ▶,c ▶, 2011 ▶); Che et al. (2009 ▶).

Experimental

Crystal data

(C6H9N2)2[Cu(C6H2N2O4)2(H2O)2]·6H2O M = 758.16 Triclinic, a = 6.7353 (3) Å b = 8.0757 (4) Å c = 15.0170 (6) Å α = 79.450 (4)° β = 86.320 (4)° γ = 89.828 (4)° V = 801.31 (6) Å3 Z = 1 Mo Kα radiation μ = 0.77 mm−1 T = 100 K 0.20 × 0.18 × 0.18 mm

Data collection

Oxford Diffraction KM-4-CCD diffractometer Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2010) ▶ T min = 0.845, T max = 0.910 7090 measured reflections 3758 independent reflections 3230 reflections with I > 2σ(I) R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.030 wR(F 2) = 0.082 S = 1.09 3758 reflections 224 parameters H-atom parameters constrained Δρmax = 0.55 e Å−3 Δρmin = −0.21 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2010) ▶; cell refinement: CrysAlis RED (Oxford Diffraction, 2010) ▶; data reduction: CrysAlis RED ▶; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008981/wm2462sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008981/wm2462Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
(C6H9N2)2[Cu(C6H2N2O4)2(H2O)2]·6H2OZ = 1
Mr = 758.16F(000) = 395
Triclinic, P1Dx = 1.571 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.7353 (3) ÅCell parameters from 3230 reflections
b = 8.0757 (4) Åθ = 3.0–28.6°
c = 15.0170 (6) ŵ = 0.77 mm−1
α = 79.450 (4)°T = 100 K
β = 86.320 (4)°Block, blue
γ = 89.828 (4)°0.20 × 0.18 × 0.18 mm
V = 801.31 (6) Å3
Oxford Diffraction KM-4-CCD diffractometer3758 independent reflections
Radiation source: fine-focus sealed tube3230 reflections with I > 2σ(I)
graphiteRint = 0.015
ω scansθmax = 28.6°, θmin = 3.0°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2010)h = −8→8
Tmin = 0.845, Tmax = 0.910k = −10→10
7090 measured reflectionsl = −18→20
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082H-atom parameters constrained
S = 1.09w = 1/[σ2(Fo2) + (0.0454P)2 + 0.2055P] where P = (Fo2 + 2Fc2)/3
3758 reflections(Δ/σ)max < 0.001
224 parametersΔρmax = 0.55 e Å−3
0 restraintsΔρmin = −0.21 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. The X-ray data were collected at 100 K using a KM4-CCD diffractometer and graphite-monochromated MoKalpha radiation generated from Oxford Diffraction X-ray tube operated at 50 kV and 25 mA. The obtained images were indexed, integrated, and scaled using the Oxford Diffraction data reduction package. The structure was solved by direct methods using SHELXS97 and refined by the full?matrix least-squares method on all F2 data. The data were corrected for absorption [CrysAlis], min/max absorption coefficients for 1 are (0.845/0.910).
xyzUiso*/Ueq
Cu10.00001.00000.50000.01475 (9)
O1−0.13388 (16)0.97838 (14)0.39113 (7)0.0154 (2)
O2−0.10153 (16)0.85683 (14)0.26828 (7)0.0142 (2)
O30.32384 (16)0.80385 (14)0.16138 (7)0.0153 (2)
O40.16155 (16)0.56417 (14)0.22248 (7)0.0149 (2)
N10.20923 (19)0.86576 (16)0.44718 (8)0.0128 (3)
N20.46299 (19)0.67808 (16)0.35325 (9)0.0139 (3)
C1−0.0421 (2)0.89169 (18)0.33887 (10)0.0116 (3)
C20.1593 (2)0.82665 (18)0.36827 (10)0.0115 (3)
C30.2884 (2)0.73410 (18)0.32044 (10)0.0119 (3)
C40.2508 (2)0.69782 (19)0.22677 (10)0.0127 (3)
C50.5068 (2)0.7161 (2)0.43260 (10)0.0155 (3)
H50.62780.67620.45770.019*
C60.3820 (2)0.8123 (2)0.48003 (10)0.0150 (3)
H60.41970.83960.53550.018*
O1W−0.14082 (18)0.72777 (16)0.57622 (8)0.0229 (3)
H1W−0.23000.73210.61660.034*
H2W−0.04430.67160.59950.034*
N110.21766 (18)0.46151 (16)0.05780 (8)0.0118 (2)
H110.20530.49600.10470.014*
C110.2788 (2)0.56690 (19)−0.02005 (10)0.0123 (3)
C120.2921 (2)0.5011 (2)−0.10119 (10)0.0151 (3)
H12A0.33490.5709−0.15710.018*
C130.2428 (2)0.3360 (2)−0.09838 (11)0.0179 (3)
H130.24890.2921−0.15300.021*
C140.1833 (2)0.2305 (2)−0.01580 (11)0.0173 (3)
H140.15160.1154−0.01430.021*
C150.1715 (2)0.29512 (19)0.06241 (11)0.0143 (3)
C160.1078 (2)0.1984 (2)0.15434 (11)0.0175 (3)
H16A0.20400.21700.19780.026*
H16B0.10130.07800.15200.026*
H16C−0.02370.23650.17350.026*
N120.32229 (19)0.72626 (16)−0.01707 (9)0.0145 (3)
H12B0.31870.75750.03090.017*
H12C0.35040.7944−0.06650.017*
O5W0.48141 (18)0.24042 (15)0.31316 (8)0.0221 (3)
H5W0.58110.29660.31510.033*
H6W0.50900.17740.27710.033*
O6W0.80815 (17)0.46006 (14)0.32461 (8)0.0193 (2)
H7W0.73330.53560.32980.029*
H8W0.90460.50410.29350.029*
O7W0.59226 (16)1.03986 (14)0.18630 (7)0.0168 (2)
H9W0.67930.99040.21090.025*
H10W0.50950.96220.18110.025*
U11U22U33U12U13U23
Cu10.01330 (14)0.02161 (16)0.01211 (14)0.00441 (10)−0.00247 (10)−0.00986 (10)
O10.0136 (5)0.0207 (6)0.0143 (5)0.0036 (4)−0.0020 (4)−0.0092 (4)
O20.0148 (5)0.0174 (5)0.0123 (5)0.0007 (4)−0.0031 (4)−0.0066 (4)
O30.0180 (5)0.0170 (5)0.0116 (5)−0.0023 (4)0.0010 (4)−0.0051 (4)
O40.0158 (5)0.0153 (5)0.0150 (5)−0.0024 (4)0.0004 (4)−0.0070 (4)
N10.0137 (6)0.0145 (6)0.0108 (6)−0.0004 (5)−0.0001 (5)−0.0041 (5)
N20.0119 (6)0.0156 (6)0.0147 (6)−0.0005 (5)−0.0002 (5)−0.0042 (5)
C10.0114 (7)0.0117 (7)0.0118 (7)−0.0008 (5)0.0000 (5)−0.0023 (5)
C20.0123 (7)0.0128 (7)0.0098 (6)−0.0018 (6)−0.0007 (5)−0.0032 (5)
C30.0121 (7)0.0119 (7)0.0118 (7)−0.0028 (5)0.0004 (5)−0.0028 (5)
C40.0090 (6)0.0169 (7)0.0138 (7)0.0031 (6)−0.0004 (5)−0.0073 (6)
C50.0129 (7)0.0177 (7)0.0159 (7)−0.0008 (6)−0.0026 (6)−0.0030 (6)
C60.0152 (7)0.0183 (8)0.0124 (7)−0.0014 (6)−0.0032 (6)−0.0040 (6)
O1W0.0195 (6)0.0287 (7)0.0193 (6)−0.0008 (5)−0.0010 (5)−0.0013 (5)
N110.0120 (6)0.0141 (6)0.0105 (6)−0.0002 (5)−0.0007 (5)−0.0054 (5)
C110.0080 (6)0.0157 (7)0.0140 (7)0.0014 (5)−0.0022 (5)−0.0044 (6)
C120.0130 (7)0.0216 (8)0.0116 (7)0.0028 (6)−0.0008 (5)−0.0049 (6)
C130.0145 (7)0.0238 (8)0.0186 (8)0.0045 (6)−0.0039 (6)−0.0116 (6)
C140.0149 (7)0.0145 (7)0.0248 (8)0.0008 (6)−0.0029 (6)−0.0090 (6)
C150.0090 (6)0.0146 (7)0.0197 (7)0.0010 (5)−0.0020 (6)−0.0040 (6)
C160.0169 (7)0.0153 (7)0.0196 (8)−0.0002 (6)−0.0004 (6)−0.0010 (6)
N120.0174 (6)0.0156 (6)0.0108 (6)−0.0014 (5)−0.0007 (5)−0.0036 (5)
O5W0.0189 (6)0.0273 (6)0.0227 (6)−0.0005 (5)−0.0024 (5)−0.0110 (5)
O6W0.0181 (6)0.0179 (6)0.0211 (6)0.0005 (5)0.0031 (5)−0.0031 (5)
O7W0.0151 (5)0.0160 (5)0.0196 (6)−0.0008 (4)−0.0055 (4)−0.0024 (4)
Cu1—O1i1.9522 (10)N11—C111.3553 (19)
Cu1—O11.9522 (10)N11—C151.3685 (19)
Cu1—N1i1.9881 (13)N11—H110.8021
Cu1—N11.9882 (13)C11—N121.3301 (19)
Cu1—O1W2.4484 (13)C11—C121.413 (2)
Cu1—O1W2.4483 (12)C12—C131.367 (2)
Cu1—O1Wi2.4483 (12)C12—H12A0.9500
O1—C11.2745 (18)C13—C141.406 (2)
O2—C11.2360 (17)C13—H130.9500
O3—C41.2540 (19)C14—C151.367 (2)
O4—C41.2508 (18)C14—H140.9500
N1—C61.333 (2)C15—C161.494 (2)
N1—C21.3438 (18)C16—H16A0.9800
N2—C51.3347 (19)C16—H16B0.9800
N2—C31.349 (2)C16—H16C0.9800
C1—C21.516 (2)N12—H12B0.8045
C2—C31.394 (2)N12—H12C0.8505
C3—C41.525 (2)O5W—H5W0.8163
C5—C61.392 (2)O5W—H6W0.8210
C5—H50.9500O6W—H7W0.8018
C6—H60.9500O6W—H8W0.8180
O1W—H1W0.8314O7W—H9W0.7824
O1W—H2W0.8488O7W—H10W0.8577
O1i—Cu1—O1179.999 (1)N1—C6—C5119.66 (14)
O1i—Cu1—N1i83.11 (5)N1—C6—H6120.2
O1—Cu1—N1i96.89 (5)C5—C6—H6120.2
O1i—Cu1—N196.89 (5)H1W—O1W—H2W109.0
O1—Cu1—N183.11 (5)C11—N11—C15123.79 (13)
N1i—Cu1—N1180.000 (2)C11—N11—H11120.1
O1i—Cu1—O1W90.35 (4)C15—N11—H11116.1
O1—Cu1—O1W89.65 (4)N12—C11—N11119.09 (13)
N1i—Cu1—O1W94.44 (5)N12—C11—C12123.08 (14)
N1—Cu1—O1W85.56 (5)N11—C11—C12117.82 (13)
O1i—Cu1—O1Wi89.65 (4)C13—C12—C11119.33 (14)
O1—Cu1—O1Wi90.35 (4)C13—C12—H12A120.3
N1i—Cu1—O1Wi85.56 (5)C11—C12—H12A120.3
N1—Cu1—O1Wi94.44 (5)C12—C13—C14120.91 (15)
O1W—Cu1—O1Wi180.0C12—C13—H13119.5
C1—O1—Cu1115.34 (9)C14—C13—H13119.5
C6—N1—C2119.22 (13)C15—C14—C13119.33 (14)
C6—N1—Cu1128.82 (10)C15—C14—H14120.3
C2—N1—Cu1111.95 (10)C13—C14—H14120.3
C5—N2—C3117.26 (13)C14—C15—N11118.80 (14)
O2—C1—O1126.48 (14)C14—C15—C16125.00 (14)
O2—C1—C2118.29 (13)N11—C15—C16116.19 (13)
O1—C1—C2115.23 (12)C15—C16—H16A109.5
N1—C2—C3120.38 (14)C15—C16—H16B109.5
N1—C2—C1114.31 (13)H16A—C16—H16B109.5
C3—C2—C1125.31 (13)C15—C16—H16C109.5
N2—C3—C2121.00 (13)H16A—C16—H16C109.5
N2—C3—C4115.44 (13)H16B—C16—H16C109.5
C2—C3—C4123.47 (13)C11—N12—H12B120.0
O4—C4—O3126.82 (14)C11—N12—H12C119.0
O4—C4—C3118.06 (13)H12B—N12—H12C121.0
O3—C4—C3115.00 (13)H5W—O5W—H6W106.8
N2—C5—C6122.45 (14)H7W—O6W—H8W105.5
N2—C5—H5118.8H9W—O7W—H10W103.7
C6—C5—H5118.8
N1i—Cu1—O1—C1−178.18 (10)N1—C2—C3—C4−174.52 (13)
N1—Cu1—O1—C11.82 (10)C1—C2—C3—C45.3 (2)
O1i—Cu1—N1—C60.11 (14)N2—C3—C4—O491.19 (16)
O1—Cu1—N1—C6−179.90 (14)C2—C3—C4—O4−92.28 (18)
O1i—Cu1—N1—C2179.37 (10)N2—C3—C4—O3−85.16 (17)
O1—Cu1—N1—C2−0.63 (10)C2—C3—C4—O391.36 (17)
Cu1—O1—C1—O2177.40 (12)C3—N2—C5—C6−1.2 (2)
Cu1—O1—C1—C2−2.51 (16)C2—N1—C6—C5−0.4 (2)
C6—N1—C2—C3−1.3 (2)Cu1—N1—C6—C5178.80 (11)
Cu1—N1—C2—C3179.36 (11)N2—C5—C6—N11.8 (2)
C6—N1—C2—C1178.89 (13)C15—N11—C11—N12−179.23 (13)
Cu1—N1—C2—C1−0.45 (15)C15—N11—C11—C121.1 (2)
O2—C1—C2—N1−177.94 (13)N12—C11—C12—C13−179.40 (15)
O1—C1—C2—N11.98 (19)N11—C11—C12—C130.2 (2)
O2—C1—C2—C32.3 (2)C11—C12—C13—C14−1.3 (2)
O1—C1—C2—C3−177.83 (13)C12—C13—C14—C151.1 (2)
C5—N2—C3—C2−0.5 (2)C13—C14—C15—N110.2 (2)
C5—N2—C3—C4176.09 (13)C13—C14—C15—C16179.08 (14)
N1—C2—C3—N21.8 (2)C11—N11—C15—C14−1.3 (2)
C1—C2—C3—N2−178.38 (13)C11—N11—C15—C16179.68 (13)
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O5Wii0.831.972.7841 (17)166
O1W—H2W···O6Wiii0.852.183.0199 (17)172
O5W—H5W···O6W0.822.052.8640 (17)173
O5W—H6W···O7Wiv0.821.962.7839 (16)175
O6W—H7W···N20.802.192.9688 (17)162
O6W—H8W···O4v0.821.992.7921 (16)168
O7W—H9W···O2v0.781.972.7559 (15)177
O7W—H10W···O30.861.872.7221 (16)176
N11—H11···O40.801.952.7522 (16)175
N12—H12B···O30.802.062.8623 (17)172
N12—H12C···O7Wvi0.852.052.9014 (17)178
C5—H5···O1Wv0.952.533.3206 (19)141
C6—H6···O5Wiii0.952.383.2485 (19)151
C13—H13···O2vii0.952.533.4081 (19)153
C16—H16B···O2iv0.982.583.2419 (19)125
Table 1

Selected bond lengths (Å)

Cu1—O11.9522 (10)
Cu1—N11.9882 (13)
Cu1—O1W2.4484 (13)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1W—H1W⋯O5Wi0.831.972.7841 (17)166
O1W—H2W⋯O6Wii0.852.183.0199 (17)172
O5W—H5W⋯O6W0.822.052.8640 (17)173
O5W—H6W⋯O7Wiii0.821.962.7839 (16)175
O6W—H7W⋯N20.802.192.9688 (17)162
O6W—H8W⋯O4iv0.821.992.7921 (16)168
O7W—H9W⋯O2iv0.781.972.7559 (15)177
O7W—H10W⋯O30.861.872.7221 (16)176
N11—H11⋯O40.801.952.7522 (16)175
N12—H12B⋯O30.802.062.8623 (17)172
N12—H12C⋯O7Wv0.852.052.9014 (17)178
C5—H5⋯O1Wiv0.952.533.3206 (19)141
C6—H6⋯O5Wii0.952.383.2485 (19)151
C13—H13⋯O2vi0.952.533.4081 (19)153
C16—H16B⋯O2iii0.982.583.2419 (19)125

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

  5 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(2-amino-4-methyl-pyrimidin-3-ium) trans-diaqua-bis-(pyrazine-2,3-di-car-boxylato)cobaltate(II) hexa-hydrate.

Authors:  Hossein Eshtiagh-Hosseini; Marek Necas; Nafiseh Alfi; Masoud Mirzaei
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-09-30

3.  catena-Poly[diacridinium [zinc(II)-di-μ-pyrazine-2,3-dicarboxyl-ato-κN,O:O;O:N,O]].

Authors:  Hossein Eshtiagh-Hosseini; Hossein Aghabozorg; Masoud Mirzaei
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-07-03

4.  Bis(2-amino-4-methyl-pyridinium) trans-diaqua-bis-(pyrazine-2,3-dicarboxyl-ato)cuprate(II) hexa-hydrate.

Authors:  Hossein Eshtiagh-Hosseini; Fabienne Gschwind; Nafiseh Alfi; Masoud Mirzaei
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-06-23

5.  Bis(2-amino-6-methyl-pyridinium) trans-diaqua-bis-(pyrazine-2,3-dicarboxyl-ato)cobaltate(II) octa-hydrate.

Authors:  Hossein Eshtiagh-Hosseini; Nafiseh Alfi; Masoud Mirzaei; Philip E Fanwick
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-01-29
  5 in total

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