Literature DB >> 21201252

Poly[propane-1,3-diammonium [cuprate(II)-bis-(μ(2)-pyridine-2,3-dicarboxyl-ato)] trihydrate].

Hossein Aghabozorg, Ramona Khadivi, Mohammad Ghadermazi, Hoda Pasdar, Shabnam Hooshmand.   

Abstract

The title polymeric compound {(C(3)H(12)N(2))[Cu(C(7)H(3)NO(4))(2)]·3H(2)O}(n) or {(pnH(2))[Cu(py-2,3-dc)(2)]·3H(2)O}(n) (pn is propane-1,3-diamine and py-2,3-dcH(2) is pyridine-2,3-dicarboxylic acid), was synthesized by reaction of copper(II) chloride dihydrate with a proton-transfer compound, propane-1,3-diammonium pyridine-2,3-dicarboxyl-ate or (pnH(2))(py-2,3-dc), in aqueous solution. The anion is a six-coordinate complex (site symmetry ), with a distorted octa-hedral geometry around Cu(II), consisting of two bidentate pyridine-2,3-dicarboxyl-ate groups and two O atoms of bridging ligands from (py-2,3-dc)(2-) fragments, which are located in trans positions. The (pnH(2))(2+) cation is disordered over two sites by the center of inversion. Inter-molecular hydrogen bonds, π-π [centroid-centroid distances of 3.539 (3) Å] and C-O⋯π stacking inter-actions [O⋯Cg = 3.240 (5) Å; Cg is the center of the pyridine ring], connect the various components into a supra-molecular structure.

Entities:  

Year:  2008        PMID： 21201252      PMCID： PMC2960456          DOI： 10.1107/S1600536807067153

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


Related literature

For related literature, see: Aghabozorg, Attar Gharamaleki, Ghadermazi et al. (2007 ▶); Aghabozorg, Attar Gharamaleki, Ghasemikhah et al. (2007 ▶); Aghabozorg, Daneshvar et al. (2007 ▶).

Experimental

Crystal data

(C3H12N2)[Cu(C7H3NO4)2]·3H2O M = 523.94 Triclinic, a = 6.6857 (12) Å b = 7.8251 (18) Å c = 9.9188 (9) Å α = 82.6561 (10)° β = 84.0079 (13)° γ = 71.9520 (17)° V = 488.20 (15) Å3 Z = 1 Mo Kα radiation μ = 1.19 mm−1 T = 100 (2) K 0.21 × 0.16 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.775, T max = 0.836 10997 measured reflections 2348 independent reflections 2310 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.063 wR(F 2) = 0.176 S = 1.01 2348 reflections 189 parameters H-atom parameters constrained Δρmax = 0.69 e Å−3 Δρmin = −0.93 e Å−3 Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXTL (Sheldrick, 1998 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807067153/om2184sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807067153/om2184Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
(C3H12N2)[Cu(C7H3NO4)2]·3H2OZ = 1
Mr = 523.94F000 = 271
Triclinic, P1Dx = 1.782 Mg m−3
a = 6.6857 (12) ÅMo Kα radiation λ = 0.71073 Å
b = 7.8251 (18) ÅCell parameters from 1234 reflections
c = 9.9188 (9) Åθ = 3–20º
α = 82.6561 (10)ºµ = 1.19 mm−1
β = 84.0079 (13)ºT = 100 (2) K
γ = 71.9520 (17)ºPrism, blue
V = 488.20 (15) Å30.21 × 0.16 × 0.15 mm
Bruker SMART APEXII CCD diffractometer2348 independent reflections
Radiation source: fine-focus sealed tube2310 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.026
T = 100(2) Kθmax = 28.0º
φ and ω scansθmin = 2.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)h = −8→8
Tmin = 0.775, Tmax = 0.836k = −10→10
10997 measured reflectionsl = −13→13
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.176  w = 1/[σ2(Fo2) + (0.010P)2 + 9.P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
2348 reflectionsΔρmax = 0.69 e Å−3
189 parametersΔρmin = −0.93 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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)
Cu10.00001.00001.00000.0083 (2)
O10.1529 (5)1.0909 (5)0.8418 (4)0.0137 (7)
O20.4743 (6)1.0337 (6)0.7330 (4)0.0233 (9)
O30.7857 (6)0.6603 (5)0.7152 (4)0.0189 (8)
O40.9507 (6)0.7923 (5)0.8365 (4)0.0184 (8)
N10.2805 (6)0.8300 (5)1.0351 (4)0.0099 (8)
C10.4291 (7)0.8457 (6)0.9349 (5)0.0098 (9)
C20.6352 (8)0.7332 (6)0.9342 (5)0.0108 (9)
C30.6889 (8)0.6039 (6)1.0472 (5)0.0119 (9)
H30.82920.52601.05250.014*
C40.5387 (8)0.5903 (6)1.1494 (5)0.0113 (9)
H40.57430.50311.22590.014*
C50.3353 (8)0.7039 (6)1.1406 (5)0.0111 (9)
H50.23140.69241.21120.013*
C60.3515 (8)1.0015 (7)0.8261 (5)0.0135 (9)
C70.8024 (7)0.7337 (7)0.8180 (5)0.0135 (10)
N20.4757 (13)0.7636 (12)0.5189 (9)0.0129 (16)0.50
H2A0.55740.73190.59130.019*0.50
H2B0.53690.82360.45040.019*0.50
H2C0.46270.66240.48920.019*0.50
C80.2618 (16)0.8836 (14)0.5611 (10)0.0139 (19)0.50
H8A0.26731.00860.56100.017*0.50
H8B0.21880.84150.65490.017*0.50
C90.1014 (16)0.8816 (14)0.4648 (11)0.014 (2)0.50
H9A0.08840.75820.47040.017*0.50
H9B0.15060.91400.37020.017*0.50
C10−0.1138 (17)1.0139 (15)0.4993 (11)0.017 (2)0.50
H10A−0.22260.98320.45500.020*0.50
H10B−0.14671.00080.59900.020*0.50
N3−0.1232 (14)1.2052 (12)0.4541 (9)0.0135 (16)0.50
H3B−0.25961.27640.46030.020*0.50
H3C−0.06961.21380.36620.020*0.50
H3D−0.04611.24220.50830.020*0.50
O1WA0.0811 (17)0.3649 (16)0.6306 (12)0.015 (2)0.50
O1WB0.1490 (17)0.3949 (16)0.6312 (13)0.018 (2)0.50
H3W0.12760.33210.71410.027*
H4W−0.01080.47940.65690.027*
O2W0.4409 (12)0.4057 (11)0.4800 (8)0.0171 (15)0.50
H1W0.36640.35850.54220.026*0.50
H2W0.37010.38700.42010.026*0.50
U11U22U33U12U13U23
Cu10.0047 (4)0.0081 (4)0.0105 (4)−0.0008 (3)0.0010 (3)0.0011 (3)
O10.0095 (16)0.0141 (17)0.0131 (17)0.0005 (13)0.0002 (13)0.0039 (13)
O20.0120 (18)0.029 (2)0.019 (2)0.0007 (16)0.0054 (15)0.0113 (16)
O30.0152 (18)0.024 (2)0.0127 (18)−0.0001 (15)0.0009 (14)−0.0029 (15)
O40.0134 (17)0.0167 (18)0.023 (2)−0.0041 (14)0.0063 (15)−0.0012 (15)
N10.0093 (18)0.0090 (18)0.0103 (19)−0.0011 (15)0.0015 (15)−0.0022 (14)
C10.008 (2)0.012 (2)0.010 (2)−0.0044 (17)−0.0004 (16)−0.0005 (17)
C20.011 (2)0.011 (2)0.011 (2)−0.0048 (17)−0.0024 (17)0.0010 (17)
C30.013 (2)0.010 (2)0.013 (2)−0.0022 (17)−0.0039 (18)−0.0027 (17)
C40.014 (2)0.009 (2)0.012 (2)−0.0034 (17)−0.0036 (17)0.0005 (17)
C50.016 (2)0.010 (2)0.010 (2)−0.0061 (18)−0.0015 (17)−0.0026 (17)
C60.006 (2)0.017 (2)0.013 (2)−0.0005 (18)0.0021 (17)0.0030 (18)
C70.007 (2)0.015 (2)0.012 (2)0.0036 (17)−0.0006 (17)0.0041 (18)
N20.011 (4)0.016 (4)0.010 (4)−0.003 (3)0.002 (3)0.000 (3)
C80.014 (5)0.014 (5)0.012 (4)−0.002 (4)0.004 (4)−0.004 (4)
C90.012 (5)0.012 (5)0.017 (5)−0.003 (4)0.002 (4)0.000 (4)
C100.018 (5)0.013 (5)0.016 (5)−0.004 (4)0.004 (4)0.000 (4)
N30.015 (4)0.012 (4)0.012 (4)−0.002 (3)0.000 (3)0.001 (3)
O1WA0.014 (6)0.018 (5)0.010 (4)−0.002 (4)0.005 (4)0.000 (3)
O1WB0.016 (6)0.016 (5)0.016 (4)0.001 (4)0.006 (4)0.001 (3)
O2W0.014 (3)0.020 (4)0.017 (4)−0.007 (3)0.002 (3)−0.002 (3)
Cu1—O1i1.960 (4)C5—H50.9500
Cu1—O11.960 (4)N2—C81.499 (12)
Cu1—N1i1.970 (4)N2—H2A0.9100
Cu1—N11.970 (4)N2—H2B0.9100
Cu1—O4ii2.549 (4)N2—H2C0.9100
Cu1—O4iii2.549 (4)C8—C91.513 (14)
O1—C61.298 (6)C8—H8A0.9900
O2—C61.225 (6)C8—H8B0.9900
O3—C71.263 (7)C9—C101.524 (14)
O4—C71.252 (7)C9—H9A0.9900
O4—Cu1iv2.549 (4)C9—H9B0.9900
N1—C51.340 (6)C10—N31.491 (13)
N1—C11.352 (6)C10—H10A0.9900
C1—C21.386 (7)C10—H10B0.9900
C1—C61.520 (7)N3—H3B0.9100
C2—C31.406 (7)N3—H3C0.9100
C2—C71.520 (7)N3—H3D0.9100
C3—C41.369 (7)O1WA—H3W0.8934
C3—H30.9500O1WA—H4W0.9660
C4—C51.379 (7)O2W—H1W0.8700
C4—H40.9500O2W—H2W0.8498
O1i—Cu1—O1180.000 (1)N1—C5—C4121.7 (5)
O1i—Cu1—N1i83.39 (16)C4—C5—Cu1152.8 (4)
O1—Cu1—N1i96.61 (16)N1—C5—H5119.1
O1i—Cu1—N196.61 (16)C4—C5—H5119.1
O1—Cu1—N183.39 (16)Cu1—C5—H588.0
N1i—Cu1—N1180.000 (1)O2—C6—O1125.3 (5)
O1i—Cu1—O4ii96.02 (14)O2—C6—C1119.8 (4)
O1—Cu1—O4ii83.98 (14)O1—C6—C1114.9 (4)
N1i—Cu1—O4ii90.52 (15)O2—C6—Cu1165.3 (4)
N1—Cu1—O4ii89.48 (15)C1—C6—Cu174.8 (3)
O1i—Cu1—O4iii83.98 (14)O4—C7—O3126.2 (5)
O1—Cu1—O4iii96.02 (14)O4—C7—C2118.0 (5)
N1i—Cu1—O4iii89.48 (15)O3—C7—C2115.5 (4)
N1—Cu1—O4iii90.52 (15)N2—C8—C9110.5 (8)
O4ii—Cu1—O4iii180.000 (1)N2—C8—H8A109.5
C6—O1—Cu1114.8 (3)C9—C8—H8A109.5
C7—O4—Cu1iv134.2 (3)N2—C8—H8B109.5
C5—N1—C1118.9 (4)C9—C8—H8B109.5
C5—N1—Cu1128.3 (3)H8A—C8—H8B108.1
C1—N1—Cu1112.8 (3)C8—C9—C10111.4 (9)
N1—C1—C2122.9 (4)C8—C9—H9A109.3
N1—C1—C6113.9 (4)C10—C9—H9A109.3
C2—C1—C6123.2 (4)C8—C9—H9B109.3
C2—C1—Cu1163.3 (4)C10—C9—H9B109.3
C6—C1—Cu173.4 (3)H9A—C9—H9B108.0
C1—C2—C3116.9 (4)N3—C10—C9112.5 (8)
C1—C2—C7124.9 (4)N3—C10—H10A109.1
C3—C2—C7118.1 (4)C9—C10—H10A109.1
C4—C3—C2119.9 (5)N3—C10—H10B109.1
C4—C3—H3120.0C9—C10—H10B109.1
C2—C3—H3120.0H10A—C10—H10B107.8
C3—C4—C5119.6 (5)H3W—O1WA—H4W91.9
C3—C4—H4120.2H1W—O2W—H2W88.7
C5—C4—H4120.2
N1i—Cu1—O1—C6−176.6 (4)C3—C4—C5—Cu11.2 (10)
N1—Cu1—O1—C63.4 (4)O1i—Cu1—C5—N1176.7 (4)
O4ii—Cu1—O1—C6−86.8 (4)O1—Cu1—C5—N1−3.3 (4)
O4iii—Cu1—O1—C693.2 (4)N1i—Cu1—C5—N1180.000 (3)
O1i—Cu1—N1—C5−3.2 (4)O4ii—Cu1—C5—N181.2 (4)
O1—Cu1—N1—C5176.8 (4)O4iii—Cu1—C5—N1−98.8 (4)
O4ii—Cu1—N1—C5−99.2 (4)O1i—Cu1—C5—C4173.2 (8)
O4iii—Cu1—N1—C580.8 (4)O1—Cu1—C5—C4−6.8 (8)
O1i—Cu1—N1—C1175.0 (3)N1i—Cu1—C5—C4176.5 (7)
O1—Cu1—N1—C1−5.0 (3)N1—Cu1—C5—C4−3.5 (7)
O4ii—Cu1—N1—C179.0 (3)O4ii—Cu1—C5—C477.6 (7)
O4iii—Cu1—N1—C1−101.0 (3)O4iii—Cu1—C5—C4−102.4 (7)
C5—N1—C1—C22.0 (7)Cu1—O1—C6—O2178.7 (5)
Cu1—N1—C1—C2−176.4 (4)Cu1—O1—C6—C1−1.2 (6)
C5—N1—C1—C6−176.0 (4)N1—C1—C6—O2177.1 (5)
Cu1—N1—C1—C65.6 (5)C2—C1—C6—O2−1.0 (8)
C5—N1—C1—Cu1178.4 (6)Cu1—C1—C6—O2−179.1 (6)
O1i—Cu1—C1—N1−5.9 (4)N1—C1—C6—O1−3.0 (7)
O1—Cu1—C1—N1174.1 (4)C2—C1—C6—O1179.0 (5)
N1i—Cu1—C1—N1180.000 (3)Cu1—C1—C6—O10.8 (4)
O4ii—Cu1—C1—N1−99.6 (3)N1—C1—C6—Cu1−3.8 (4)
O4iii—Cu1—C1—N180.4 (3)C2—C1—C6—Cu1178.2 (5)
O1i—Cu1—C1—C24.7 (13)O1i—Cu1—C6—O2176.0 (15)
O1—Cu1—C1—C2−175.3 (13)O1—Cu1—C6—O2−4.0 (15)
N1i—Cu1—C1—C2−169.4 (11)N1i—Cu1—C6—O2−0.1 (18)
N1—Cu1—C1—C210.6 (11)N1—Cu1—C6—O2179.9 (18)
O4ii—Cu1—C1—C2−89.0 (12)O4ii—Cu1—C6—O286.3 (17)
O4iii—Cu1—C1—C291.0 (12)O4iii—Cu1—C6—O2−93.7 (17)
O1i—Cu1—C1—C6179.4 (3)O1i—Cu1—C6—O1180.000 (2)
O1—Cu1—C1—C6−0.6 (3)N1i—Cu1—C6—O13.9 (4)
N1i—Cu1—C1—C65.3 (5)N1—Cu1—C6—O1−176.1 (4)
N1—Cu1—C1—C6−174.7 (5)O4ii—Cu1—C6—O190.3 (4)
O4ii—Cu1—C1—C685.7 (3)O4iii—Cu1—C6—O1−89.7 (4)
O4iii—Cu1—C1—C6−94.3 (3)O1i—Cu1—C6—C1−1.1 (5)
N1—C1—C2—C3−2.9 (7)O1—Cu1—C6—C1178.9 (5)
C6—C1—C2—C3175.0 (4)N1i—Cu1—C6—C1−177.2 (3)
Cu1—C1—C2—C3−11.1 (15)N1—Cu1—C6—C12.8 (3)
N1—C1—C2—C7174.0 (5)O4ii—Cu1—C6—C1−90.8 (3)
C6—C1—C2—C7−8.2 (8)O4iii—Cu1—C6—C189.2 (3)
Cu1—C1—C2—C7165.8 (10)Cu1iv—O4—C7—O3164.8 (4)
C1—C2—C3—C41.8 (7)Cu1iv—O4—C7—C2−21.4 (7)
C7—C2—C3—C4−175.3 (4)C1—C2—C7—O4109.8 (6)
C2—C3—C4—C50.0 (7)C3—C2—C7—O4−73.4 (6)
C1—N1—C5—C40.0 (7)C1—C2—C7—O3−75.7 (6)
Cu1—N1—C5—C4178.1 (4)C3—C2—C7—O3101.1 (5)
C1—N1—C5—Cu1−178.1 (7)N2—C8—C9—C10−175.6 (8)
C3—C4—C5—N1−1.0 (7)C8—C9—C10—N376.1 (11)
D—H···AD—HH···AD···AD—H···A
N2—H2A···O30.911.962.854 (1)167
N2—H2B···O2v0.912.012.830 (1)150
N3—H3B···N2vi0.911.562.283 (1)134
N3—H3B···O2Wvii0.911.952.852 (13)174
N3—H3C···O3v0.912.423.041 (10)126
N3—H3C···O4v0.912.082.991 (1)174
N3—H3D···O1WAviii0.912.032.934 (1)170
N3—H3D···O1WBviii0.912.513.407 (15)170
O1WA—H3W···O1ix0.892.112.764 (1)130
O1WA—H4W···O3ii0.971.742.696 (1)168
O2W—H1W···O1WA0.872.002.779 (15)148
O2W—H1W···O1WB0.871.592.350 (1)145
O2W—H2W···O3x0.851.922.768 (1)179
C5—H5···O1WAxi0.952.603.534 (13)169
C8—H8A···O20.992.372.891 (11)112
C8—H8B···O4ii0.992.493.396 (11)153
Cu1—O11.960 (4)
Cu1—N11.970 (4)
Cu1—O4i2.549 (4)
O1ii—Cu1—N1ii83.39 (16)
O1—Cu1—N1ii96.61 (16)
O4i—Cu1—O4iii180

Symmetry codes: (i) ; (ii) ; (iii) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N2—H2A⋯O30.911.962.854 (1)167
N2—H2B⋯O2iv0.912.012.830 (1)150
N3—H3B⋯N2v0.911.562.283 (1)134
N3—H3B⋯O2Wvi0.911.952.852 (13)174
N3—H3C⋯O3iv0.912.423.041 (10)126
N3—H3C⋯O4iv0.912.082.991 (1)174
N3—H3D⋯O1WAvii0.912.032.934 (1)170
N3—H3D⋯O1WBvii0.912.513.407 (15)170
O1WA—H3W⋯O1viii0.892.112.764 (1)130
O1WA—H4W⋯O3i0.971.742.696 (1)168
O2W—H1W⋯O1WA0.872.002.779 (15)148
O2W—H1W⋯O1WB0.871.592.350 (1)145
O2W—H2W⋯O3ix0.851.922.768 (1)179
C5—H5⋯O1WAx0.952.603.534 (13)169
C8—H8A⋯O20.992.372.891 (11)112
C8—H8B⋯O4i0.992.493.396 (11)153

Symmetry codes: (i) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) ; (x) .

  1 in total

1.  Bis-(μ-pyridine-2,3-dicarboxyl-ato)bis-[aqua-(3-carb-oxy-pyridine-2-carboxyl-ato)indium(III)] tetra-hydrate.

Authors:  H Eshtiagh-Hosseini; M Mirzaei; A Mousavinezhad; M Necas; J T Mague
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-12-21
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