DOI: 10.1002/anie.199306131. 2,2′‐Bipyrimidineoxalatocopper(<scp>II</scp>) Complexes: From the Mononuclear Complex to the 2D Sheetlike Polymer

2,2′‐Bipyrimidineoxalatocopper(II) Complexes: From the Mononuclear Complex to the 2D Sheetlike Polymer

10.1002/anie.199306131

Crossref journal-article

Wiley

Angewandte Chemie International Edition in English (311)

Bibliography

De Munno, G., Julve, M., Nicolo, F., Lloret, F., Faus, J., Ruiz, R., & Sinn, E. (1993). 2,2â²âBipyrimidineoxalatocopper(II) Complexes: From the Mononuclear Complex to the 2D Sheetlike Polymer. Angewandte Chemie International Edition in English, 32(4), 613â615. Portico.

Authors 7

Giovanni De Munno (first)
Miguel Julve (additional)
Francesco Nicolo (additional)
Frances Lloret (additional)
Juan Faus (additional)
Rafael Ruiz (additional)
Ekkehard Sinn (additional)

References 22 Referenced 138

10.1021/cr60211a001
I.Castro J.Faus M.Julve A.Gleizes J. Chem. Soc. Dalton Trans.1991 1937 and references therein. (10.1039/DT9910001937)
10.1002/ange.19850971008
10.1002/anie.198508341
10.1021/ic00041a025
A.Gleizes M.Julve M.Verdaguer J. A.Real J.Faus X.Solans J. Chem. Soc. Dalton Trans.1992 3209.
10.1021/ic00300a023
H.Okawa N.Matsumoto H.Tamaki Communication presented at the 29th I.C.C. Switzerland1992.
10.1021/ic50203a060
10.1021/ic50213a015
10.1021/ic00191a028
I.Castro M.Julve G.De Munno J. A.Real F.Lloret J.Faus J. Chem. Soc. Dalton Trans.1992 1739 and references therein. (10.1039/DT9920001739)
10.1021/ic00220a030
10.1021/ic00291a023
(c)M.Julve M.Verdaguer G.De Munno J. A.Real G.Bruno Inorg. Chem. in press.
10.1021/ic00347a033
X‐ray structure analyses: Siemens R3m/V automatic diffractometer MoKα λ = 0.71073 Å graphite monochromator 298 K. Data collection solution and refinement: ω‐2θ standard Patterson methods with subsequent Fourier recycling SHELXTL‐PLUS [11].1: C10H20N4CuO11(Mr= 435.6) orthorhombic space groupP212121 a= 6.544(2) b= 13.838(4) c= 19.319(7) Å V= 1749.4(10) Å3 Z= 4 ρcalcd= 1.655 g cm−3 μ = 13.1 cm−1 2θ range 3–50° crystal size 0.35 × 0.38 × 0.20 mm3 F(000) = 900. 1803 unique reflections and 1475 assumed as observed withI> 3σ(I). Refinement of 199 variables with anisotropic thermal parameters for all non‐hydrogen atoms (except the oxygen atoms of water molecules) gaveR(F0) = 0.0525 Rw(F0) = 0.0613 andS= 1.49 withw−1= σ2(F0) + 0.002395(F0)2.2: C12H16N4Cu2O13(Mr= 551.4) monoclinic space groupC2/m a= 9.445(2) b= 16.622(3) c= 6.202(1) Å β = 101.4(1)° V= 954.6(3) Å3 Z= 2 ρcalcd= 1.918 g cm−3 μ = 23.1 cm−1 2θ range 3–55° crystal size 0.34 × 0.19 × 0.23 mm3 F(000) = 556. 1147 unique reflections and 981 assumed as observed withI> 3σ(I). Ψ‐scan absorption correction was applied (max. and min. transmission factors 0.355/0.472) [12]. Refinement of 86 variables with anisotropic thermal parameters for all non‐hydrogen atoms gaveR(F0) = 0.0420 Rw(F0) = 0.0470 andS= 1.67 withw−1= σ2(F0) + 0.001000(F0)2. The space group of2cannot be uniquely determined from the systematic absences which only indicate the presence of aC‐centered cell; the choice is between the acentricC2 orCmgroups and the centricC2/mone. The latter was favored by the intensities statistics and consequently the structure solution and refinement were carried out in the centrosymmetric space group. The analysis of the residual electronic density in a final difference‐Fourier map revealed three distinct peaks (two. O(4) and O(5) in general positions and one O(3) in special position on a twofold axis) which could be interpreted as crystallization water molecules. The elemental analysis indicated a 5:2 ratio between the crystallization water and copper. Five oxygen atoms of the water molecules may be obtained by applying the twofold axis operation to the three peaks while 10 positions are obtained when also the mirror operation is also applied. Then we tried to refine the structure inC2 andCm but all our attempts gave worse results with large correlations between atomic positional parameters. Therefore the refinement was completed inC2/mby assuming a disordered disposition of the water molecules in which 10 half oxygen atoms are arranged as two staggered five‐membered rings. Further details of the crystal structure investigations are available on request from the Fachinformationszentrum Karlsruhe. Gesellschaft für wissenschaftlich‐technische Information mbH D‐W‐7514 Eggenstein‐Leopoldshafen 2 (FRG) on quoting the depository number CSD‐56958 the names of the authors and the journal citation.
SHELXTL PLUS Version 3.4. Siemens Analytical X‐Ray Instruments Inc. Madison WI 1989.
10.1107/S0567739468000707
Bond lengths and angles in the bpym and oxalato ligands are in agreement with those reported in the literature. Although the pyrimidyl rings of bpym are planar the ligand as a whole is not planar (the dihedral angle between the six‐membered pyrimjdyl rings is 4.4(3)°). The oxalato ligand is quite planar; the maximum deviation from the mean plane is 0.077(7) Å at O(2). The dihedral angle between the mean planes of the bpym and oxalato ligands is 7.1(2)°. The OC bond lengths of oxalate occur in two sets (1.281(9) and 1.267(9) Å for O(2)–C(9) and O(1)–C(10)) and 1.248(10) and 1.212(12) Å for O(3)–C(9) and O(4)–C(10)) as a result of its bidentate coordination to copper.
The bpym and oxalato ligands are planar and form a dihedral angle of 99.4(1)°. The OC bond lengths in the oxalato ligand in2are all identical (1.242(4) Å) on account of its quasi‐symmetrical bischelating coordination to copper.
The disorder is such that two sets of five half oxygen atoms are arranged as a ten‐membered ring (O…︁O separation ca. 1.4 Å) formed by two staggered pentagons. For clarity only one set of five atoms is shown in the top picture in Figure 2 where it should be noted that O(3) lies on the twofold axis. The five water molecules are almost planar (the largest deviation from the mean plane is 0.07(1) Å. The dihedral angle between this plane ant that of bpym is 15.7(2).

Dates

Type	When
Created	21 years, 7 months ago (Dec. 30, 2003, 5:07 p.m.)
Deposited	1 year, 9 months ago (Oct. 25, 2023, 7:58 a.m.)
Indexed	1 month, 3 weeks ago (July 2, 2025, 1:51 p.m.)
Issued	32 years, 4 months ago (April 1, 1993)
Published	32 years, 4 months ago (April 1, 1993)
Published Online	21 years, 8 months ago (Dec. 22, 2003)
Published Print	32 years, 4 months ago (April 1, 1993)

Funders 0

None

BibTeX

@article{De_Munno_1993, title={2,2′‐Bipyrimidineoxalatocopper(<scp>II</scp>) Complexes: From the Mononuclear Complex to the 2D Sheetlike Polymer}, volume={32}, ISSN={0570-0833}, url={http://dx.doi.org/10.1002/anie.199306131}, DOI={10.1002/anie.199306131}, number={4}, journal={Angewandte Chemie International Edition in English}, publisher={Wiley}, author={De Munno, Giovanni and Julve, Miguel and Nicolo, Francesco and Lloret, Frances and Faus, Juan and Ruiz, Rafael and Sinn, Ekkehard}, year={1993}, month=apr, pages={613–615} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        7,
        2
      ]
    ],
    "date-time": "2025-07-02T17:51:43Z",
    "timestamp": 1751478703674
  },
  "reference-count": 22,
  "publisher": "Wiley",
  "issue": "4",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2003,
            12,
            22
          ]
        ],
        "date-time": "2003-12-22T00:00:00Z",
        "timestamp": 1072051200000
      },
      "content-version": "vor",
      "delay-in-days": 3917,
      "URL": "http://onlinelibrary.wiley.com/termsAndConditions#vor"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        1993,
        4
      ]
    ]
  },
  "DOI": "10.1002/anie.199306131",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2003,
        12,
        30
      ]
    ],
    "date-time": "2003-12-30T22:07:25Z",
    "timestamp": 1072822045000
  },
  "page": "613-615",
  "source": "Crossref",
  "is-referenced-by-count": 138,
  "title": "2,2\u2032\u2010Bipyrimidineoxalatocopper(<scp>II</scp>) Complexes: From the Mononuclear Complex to the 2D Sheetlike Polymer",
  "prefix": "10.1002",
  "volume": "32",
  "author": [
    {
      "given": "Giovanni",
      "family": "De Munno",
      "sequence": "first",
      "affiliation": []
    },
    {
      "given": "Miguel",
      "family": "Julve",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Francesco",
      "family": "Nicolo",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Frances",
      "family": "Lloret",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Juan",
      "family": "Faus",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Rafael",
      "family": "Ruiz",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Ekkehard",
      "family": "Sinn",
      "sequence": "additional",
      "affiliation": []
    }
  ],
  "member": "311",
  "published-online": {
    "date-parts": [
      [
        2003,
        12,
        22
      ]
    ]
  },
  "reference": [
    {
      "key": "e_1_2_1_1_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/cr60211a001"
    },
    {
      "key": "e_1_2_1_2_2",
      "doi-asserted-by": "crossref",
      "unstructured": "I.Castro J.Faus M.Julve A.Gleizes J. Chem. Soc. Dalton Trans.1991 1937 and references therein.",
      "DOI": "10.1039/DT9910001937"
    },
    {
      "key": "e_1_2_1_3_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/ange.19850971008"
    },
    {
      "key": "e_1_2_1_3_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1002/anie.198508341"
    },
    {
      "key": "e_1_2_1_3_4",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ic00041a025"
    },
    {
      "key": "e_1_2_1_3_5",
      "unstructured": "A.Gleizes M.Julve M.Verdaguer J. A.Real J.Faus X.Solans J. Chem. Soc. Dalton Trans.1992 3209."
    },
    {
      "key": "e_1_2_1_4_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ic00300a023"
    },
    {
      "key": "e_1_2_1_4_3",
      "unstructured": "H.Okawa N.Matsumoto H.Tamaki Communication presented at the 29th I.C.C. Switzerland1992."
    },
    {
      "key": "e_1_2_1_5_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ic50203a060"
    },
    {
      "key": "e_1_2_1_5_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ic50213a015"
    },
    {
      "key": "e_1_2_1_6_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ic00191a028"
    },
    {
      "key": "e_1_2_1_7_2",
      "doi-asserted-by": "crossref",
      "unstructured": "I.Castro M.Julve G.De Munno J. A.Real F.Lloret J.Faus J. Chem. Soc. Dalton Trans.1992 1739 and references therein.",
      "DOI": "10.1039/DT9920001739"
    },
    {
      "key": "e_1_2_1_8_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ic00220a030"
    },
    {
      "key": "e_1_2_1_8_3",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ic00291a023"
    },
    {
      "key": "e_1_2_1_8_4",
      "unstructured": "(c)M.Julve M.Verdaguer G.De Munno J. A.Real G.Bruno Inorg. Chem. in press."
    },
    {
      "key": "e_1_2_1_9_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ic00347a033"
    },
    {
      "key": "e_1_2_1_10_2",
      "unstructured": "X\u2010ray structure analyses: Siemens R3m/V automatic diffractometer MoK\u03b1 \u03bb = 0.71073 \u00c5 graphite monochromator 298 K. Data collection solution and refinement: \u03c9\u20102\u03b8 standard Patterson methods with subsequent Fourier recycling SHELXTL\u2010PLUS [11].1: C10H20N4CuO11(Mr= 435.6) orthorhombic space groupP212121 a= 6.544(2) b= 13.838(4) c= 19.319(7) \u00c5 V= 1749.4(10) \u00c53 Z= 4 \u03c1calcd= 1.655 g cm\u22123 \u03bc = 13.1 cm\u22121 2\u03b8 range 3\u201350\u00b0 crystal size 0.35 \u00d7 0.38 \u00d7 0.20 mm3 F(000) = 900. 1803 unique reflections and 1475 assumed as observed withI> 3\u03c3(I). Refinement of 199 variables with anisotropic thermal parameters for all non\u2010hydrogen atoms (except the oxygen atoms of water molecules) gaveR(F0) = 0.0525 Rw(F0) = 0.0613 andS= 1.49 withw\u22121= \u03c32(F0) + 0.002395(F0)2.2: C12H16N4Cu2O13(Mr= 551.4) monoclinic space groupC2/m a= 9.445(2) b= 16.622(3) c= 6.202(1) \u00c5 \u03b2 = 101.4(1)\u00b0 V= 954.6(3) \u00c53 Z= 2 \u03c1calcd= 1.918 g cm\u22123 \u03bc = 23.1 cm\u22121 2\u03b8 range 3\u201355\u00b0 crystal size 0.34 \u00d7 0.19 \u00d7 0.23 mm3 F(000) = 556. 1147 unique reflections and 981 assumed as observed withI> 3\u03c3(I). \u03a8\u2010scan absorption correction was applied (max. and min. transmission factors 0.355/0.472) [12]. Refinement of 86 variables with anisotropic thermal parameters for all non\u2010hydrogen atoms gaveR(F0) = 0.0420 Rw(F0) = 0.0470 andS= 1.67 withw\u22121= \u03c32(F0) + 0.001000(F0)2. The space group of2cannot be uniquely determined from the systematic absences which only indicate the presence of aC\u2010centered cell; the choice is between the acentricC2 orCmgroups and the centricC2/mone. The latter was favored by the intensities statistics and consequently the structure solution and refinement were carried out in the centrosymmetric space group. The analysis of the residual electronic density in a final difference\u2010Fourier map revealed three distinct peaks (two. O(4) and O(5) in general positions and one O(3) in special position on a twofold axis) which could be interpreted as crystallization water molecules. The elemental analysis indicated a 5:2 ratio between the crystallization water and copper. Five oxygen atoms of the water molecules may be obtained by applying the twofold axis operation to the three peaks while 10 positions are obtained when also the mirror operation is also applied. Then we tried to refine the structure inC2 andCm but all our attempts gave worse results with large correlations between atomic positional parameters. Therefore the refinement was completed inC2/mby assuming a disordered disposition of the water molecules in which 10 half oxygen atoms are arranged as two staggered five\u2010membered rings. Further details of the crystal structure investigations are available on request from the Fachinformationszentrum Karlsruhe. Gesellschaft f\u00fcr wissenschaftlich\u2010technische Information mbH D\u2010W\u20107514 Eggenstein\u2010Leopoldshafen 2 (FRG) on quoting the depository number CSD\u201056958 the names of the authors and the journal citation."
    },
    {
      "key": "e_1_2_1_11_2",
      "unstructured": "SHELXTL PLUS Version 3.4. Siemens Analytical X\u2010Ray Instruments Inc. Madison WI 1989."
    },
    {
      "key": "e_1_2_1_12_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1107/S0567739468000707"
    },
    {
      "key": "e_1_2_1_13_2",
      "unstructured": "Bond lengths and angles in the bpym and oxalato ligands are in agreement with those reported in the literature. Although the pyrimidyl rings of bpym are planar the ligand as a whole is not planar (the dihedral angle between the six\u2010membered pyrimjdyl rings is 4.4(3)\u00b0). The oxalato ligand is quite planar; the maximum deviation from the mean plane is 0.077(7) \u00c5 at O(2). The dihedral angle between the mean planes of the bpym and oxalato ligands is 7.1(2)\u00b0. The O\uf8ffC bond lengths of oxalate occur in two sets (1.281(9) and 1.267(9) \u00c5 for O(2)\u2013C(9) and O(1)\u2013C(10)) and 1.248(10) and 1.212(12) \u00c5 for O(3)\u2013C(9) and O(4)\u2013C(10)) as a result of its bidentate coordination to copper."
    },
    {
      "key": "e_1_2_1_14_2",
      "unstructured": "The bpym and oxalato ligands are planar and form a dihedral angle of 99.4(1)\u00b0. The O\uf8ffC bond lengths in the oxalato ligand in2are all identical (1.242(4) \u00c5) on account of its quasi\u2010symmetrical bischelating coordination to copper."
    },
    {
      "key": "e_1_2_1_15_2",
      "unstructured": "The disorder is such that two sets of five half oxygen atoms are arranged as a ten\u2010membered ring (O\u2026\ufe01O separation ca. 1.4 \u00c5) formed by two staggered pentagons. For clarity only one set of five atoms is shown in the top picture in Figure 2 where it should be noted that O(3) lies on the twofold axis. The five water molecules are almost planar (the largest deviation from the mean plane is 0.07(1) \u00c5. The dihedral angle between this plane ant that of bpym is 15.7(2)."
    }
  ],
  "container-title": "Angewandte Chemie International Edition in English",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fanie.199306131",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "text-mining"
    },
    {
      "URL": "https://onlinelibrary.wiley.com/doi/pdf/10.1002/anie.199306131",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2023,
        10,
        25
      ]
    ],
    "date-time": "2023-10-25T11:58:23Z",
    "timestamp": 1698235103000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://onlinelibrary.wiley.com/doi/10.1002/anie.199306131"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        1993,
        4
      ]
    ]
  },
  "references-count": 22,
  "journal-issue": {
    "issue": "4",
    "published-print": {
      "date-parts": [
        [
          1993,
          4
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1002/anie.199306131"
  ],
  "URL": "http://dx.doi.org/10.1002/anie.199306131",
  "relation": {},
  "ISSN": [
    "0570-0833"
  ],
  "subject": [],
  "container-title-short": "Angew. Chem. Int. Ed. Engl.",
  "published": {
    "date-parts": [
      [
        1993,
        4
      ]
    ]
  }
}