<?xml version="1.0" encoding="utf-8"?>
<TEI xmlns="http://www.tei-c.org/ns/1.0" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance" xmlns:hal="http://hal.archives-ouvertes.fr/" xmlns:gml="http://www.opengis.net/gml/3.3/" xmlns:gmlce="http://www.opengis.net/gml/3.3/ce" version="1.1" xsi:schemaLocation="http://www.tei-c.org/ns/1.0 http://api.archives-ouvertes.fr/documents/aofr-sword.xsd">
  <teiHeader>
    <fileDesc>
      <titleStmt>
        <title>HAL TEI export of hal-01710280</title>
      </titleStmt>
      <publicationStmt>
        <distributor>CCSD</distributor>
        <availability status="restricted">
          <licence target="https://creativecommons.org/publicdomain/zero/1.0/">CC0 1.0 - Universal</licence>
        </availability>
        <date when="2026-05-13T00:44:28+02:00"/>
      </publicationStmt>
      <sourceDesc>
        <p part="N">HAL API Platform</p>
      </sourceDesc>
    </fileDesc>
  </teiHeader>
  <text>
    <body>
      <listBibl>
        <biblFull>
          <titleStmt>
            <title xml:lang="en">Charge density analysis of metformin chloride, a biguanide anti-hyperglycemic agent</title>
            <author role="aut">
              <persName>
                <forename type="first">Rajendran</forename>
                <surname>Niranjana Devi</surname>
              </persName>
              <idno type="halauthorid">1314640-0</idno>
              <affiliation ref="#struct-491367"/>
            </author>
            <author role="aut">
              <persName>
                <forename type="first">Christian</forename>
                <surname>Jelsch</surname>
              </persName>
              <email type="md5">60680622bd95f53410e428816daa23cb</email>
              <email type="domain">univ-lorraine.fr</email>
              <idno type="idhal" notation="string">christian-jelsch</idno>
              <idno type="idhal" notation="numeric">739072</idno>
              <idno type="halauthorid" notation="string">35249-739072</idno>
              <idno type="ORCID">https://orcid.org/0000-0002-2655-0313</idno>
              <idno type="IDREF">https://www.idref.fr/128905786</idno>
              <affiliation ref="#struct-129683"/>
            </author>
            <author role="aut">
              <persName>
                <forename type="first">Samuel</forename>
                <surname>Israel</surname>
              </persName>
              <idno type="halauthorid">1314637-0</idno>
              <affiliation ref="#struct-491367"/>
            </author>
            <author role="aut">
              <persName>
                <forename type="first">Emmanuel</forename>
                <surname>Aubert</surname>
              </persName>
              <email type="md5">88ced1b7904d7aa27f58ef11326e9604</email>
              <email type="domain">univ-lorraine.fr</email>
              <idno type="idhal" notation="string">emmanuel-aubert</idno>
              <idno type="idhal" notation="numeric">180926</idno>
              <idno type="halauthorid" notation="string">34906-180926</idno>
              <idno type="ORCID">https://orcid.org/0000-0001-7860-1349</idno>
              <idno type="IDREF">https://www.idref.fr/076428567</idno>
              <affiliation ref="#struct-129683"/>
            </author>
            <author role="aut">
              <persName>
                <forename type="first">Chellam</forename>
                <surname>Anzline</surname>
              </persName>
              <idno type="halauthorid">1314638-0</idno>
              <affiliation ref="#struct-491367"/>
            </author>
            <author role="aut">
              <persName>
                <forename type="first">Amar</forename>
                <forename type="middle">A</forename>
                <surname>Hosamani</surname>
              </persName>
              <idno type="halauthorid">1314639-0</idno>
              <affiliation ref="#struct-86671"/>
            </author>
            <editor role="depositor">
              <persName>
                <forename>Christian</forename>
                <surname>Jelsch</surname>
              </persName>
              <email type="md5">60680622bd95f53410e428816daa23cb</email>
              <email type="domain">univ-lorraine.fr</email>
            </editor>
          </titleStmt>
          <editionStmt>
            <edition n="v1" type="current">
              <date type="whenSubmitted">2018-02-15 17:35:48</date>
              <date type="whenModified">2025-11-04 14:21:30</date>
              <date type="whenReleased">2018-02-15 17:45:18</date>
              <date type="whenProduced">2017</date>
              <date type="whenEndEmbargoed">2018-02-15</date>
              <ref type="file" target="https://hal.science/hal-01710280v1/document">
                <date notBefore="2018-02-15"/>
              </ref>
              <ref type="file" subtype="greenPublisher" n="1" target="https://hal.science/hal-01710280v1/file/2017_ActaB_MetCl_reprint.pdf" id="file-1710280-1750679">
                <date notBefore="2018-02-15"/>
              </ref>
              <ref type="externalLink" target="http://journals.iucr.org/b/issues/2017/01/00/pi5029/pi5029.pdf"/>
            </edition>
            <respStmt>
              <resp>contributor</resp>
              <name key="596331">
                <persName>
                  <forename>Christian</forename>
                  <surname>Jelsch</surname>
                </persName>
                <email type="md5">60680622bd95f53410e428816daa23cb</email>
                <email type="domain">univ-lorraine.fr</email>
              </name>
            </respStmt>
          </editionStmt>
          <publicationStmt>
            <distributor>CCSD</distributor>
            <idno type="halId">hal-01710280</idno>
            <idno type="halUri">https://hal.science/hal-01710280</idno>
            <idno type="halBibtex">niranjanadevi:hal-01710280</idno>
            <idno type="halRefHtml">&lt;i&gt;Acta Crystallographica Section B : Structural Science, Crystal Engineering and Materials [2014-..]&lt;/i&gt;, 2017, 73 (1), pp.10-22. &lt;a target="_blank" href="https://dx.doi.org/10.1107/S2052520616017844"&gt;&amp;#x27E8;10.1107/S2052520616017844&amp;#x27E9;&lt;/a&gt;</idno>
            <idno type="halRef">Acta Crystallographica Section B : Structural Science, Crystal Engineering and Materials [2014-..], 2017, 73 (1), pp.10-22. &amp;#x27E8;10.1107/S2052520616017844&amp;#x27E9;</idno>
            <availability status="restricted">
              <licence target="https://about.hal.science/hal-authorisation-v1/">HAL Authorization<ref corresp="#file-1710280-1750679"/></licence>
            </availability>
          </publicationStmt>
          <seriesStmt>
            <idno type="stamp" n="CNRS">CNRS - Centre national de la recherche scientifique</idno>
            <idno type="stamp" n="UNIV-LORRAINE">Université de Lorraine</idno>
            <idno type="stamp" n="GENCI">Publications ayant eu recours aux supercalculateurs du GENCI</idno>
            <idno type="stamp" n="CRM2-UL">CRM2 - Laboratoire de Cristallographie, Résonance Magnétique et Modélisations</idno>
            <idno type="stamp" n="CPM-UL">Pôle scientifique Chimie et Physique Moléculaire de l'Université de Lorraine</idno>
          </seriesStmt>
          <notesStmt>
            <note type="audience" n="2">International</note>
            <note type="popular" n="0">No</note>
            <note type="peer" n="1">Yes</note>
          </notesStmt>
          <sourceDesc>
            <biblStruct>
              <analytic>
                <title xml:lang="en">Charge density analysis of metformin chloride, a biguanide anti-hyperglycemic agent</title>
                <author role="aut">
                  <persName>
                    <forename type="first">Rajendran</forename>
                    <surname>Niranjana Devi</surname>
                  </persName>
                  <idno type="halauthorid">1314640-0</idno>
                  <affiliation ref="#struct-491367"/>
                </author>
                <author role="aut">
                  <persName>
                    <forename type="first">Christian</forename>
                    <surname>Jelsch</surname>
                  </persName>
                  <email type="md5">60680622bd95f53410e428816daa23cb</email>
                  <email type="domain">univ-lorraine.fr</email>
                  <idno type="idhal" notation="string">christian-jelsch</idno>
                  <idno type="idhal" notation="numeric">739072</idno>
                  <idno type="halauthorid" notation="string">35249-739072</idno>
                  <idno type="ORCID">https://orcid.org/0000-0002-2655-0313</idno>
                  <idno type="IDREF">https://www.idref.fr/128905786</idno>
                  <affiliation ref="#struct-129683"/>
                </author>
                <author role="aut">
                  <persName>
                    <forename type="first">Samuel</forename>
                    <surname>Israel</surname>
                  </persName>
                  <idno type="halauthorid">1314637-0</idno>
                  <affiliation ref="#struct-491367"/>
                </author>
                <author role="aut">
                  <persName>
                    <forename type="first">Emmanuel</forename>
                    <surname>Aubert</surname>
                  </persName>
                  <email type="md5">88ced1b7904d7aa27f58ef11326e9604</email>
                  <email type="domain">univ-lorraine.fr</email>
                  <idno type="idhal" notation="string">emmanuel-aubert</idno>
                  <idno type="idhal" notation="numeric">180926</idno>
                  <idno type="halauthorid" notation="string">34906-180926</idno>
                  <idno type="ORCID">https://orcid.org/0000-0001-7860-1349</idno>
                  <idno type="IDREF">https://www.idref.fr/076428567</idno>
                  <affiliation ref="#struct-129683"/>
                </author>
                <author role="aut">
                  <persName>
                    <forename type="first">Chellam</forename>
                    <surname>Anzline</surname>
                  </persName>
                  <idno type="halauthorid">1314638-0</idno>
                  <affiliation ref="#struct-491367"/>
                </author>
                <author role="aut">
                  <persName>
                    <forename type="first">Amar</forename>
                    <forename type="middle">A</forename>
                    <surname>Hosamani</surname>
                  </persName>
                  <idno type="halauthorid">1314639-0</idno>
                  <affiliation ref="#struct-86671"/>
                </author>
              </analytic>
              <monogr>
                <idno type="halJournalId" status="VALID">116367</idno>
                <idno type="issn">2052-5206</idno>
                <idno type="eissn">2052-5206</idno>
                <title level="j">Acta Crystallographica Section B : Structural Science, Crystal Engineering and Materials [2014-...]</title>
                <imprint>
                  <publisher>International Union of Crystallography / Wiley</publisher>
                  <biblScope unit="volume">73</biblScope>
                  <biblScope unit="issue">1</biblScope>
                  <biblScope unit="pp">10-22</biblScope>
                  <date type="datePub">2017</date>
                </imprint>
              </monogr>
              <idno type="doi">10.1107/S2052520616017844</idno>
            </biblStruct>
          </sourceDesc>
          <profileDesc>
            <langUsage>
              <language ident="en">English</language>
            </langUsage>
            <textClass>
              <keywords scheme="author">
                <term xml:lang="en">electrostatic potential</term>
                <term xml:lang="en">Hirshfeld surface</term>
                <term xml:lang="en">bond order</term>
              </keywords>
              <classCode scheme="halDomain" n="chim.cris">Chemical Sciences/Cristallography</classCode>
              <classCode scheme="halDomain" n="chim.theo">Chemical Sciences/Theoretical and/or physical chemistry</classCode>
              <classCode scheme="halTypology" n="ART">Journal articles</classCode>
              <classCode scheme="halOldTypology" n="ART">Journal articles</classCode>
              <classCode scheme="halTreeTypology" n="ART">Journal articles</classCode>
            </textClass>
            <abstract xml:lang="en">
              <p>The experimental charge density analysis of the anti-hyperglycemic agent metformin chloride with high-resolution X-ray diffraction data at low temperature (100 K) has been performed and these experimental results were compared with that derived from the corresponding periodic theoretical calculations at the B3LYP/6-31G** level of theory. The experimental and theoretical multipolar charge-density analyses of metformin chloride have been accomplished in order to understand its structural and electronic properties. The C and N atoms of the molecular backbone adopt a near trigonal geometry due to the occurrence of extensive delocalization/resonance of C—N bonds, as confirmed by topological analysis and also found by Natural Resonance Theory calculations performed in the isolated metformin cation. The molecule contains six C—N bonds and the topological bond order analysis shows that four bonds have bond orders close to 4/3 and two bonds can be considered as single. The analysis of numerical parameters of the valence shell charge concentration reports that the N3 atom, which forms two bonds with C atoms, possesses one non-bonding valence-shell charge concentration (VSCC) in the direction of the electron lone pair. Among the intermolecular interactions of the chloride atom with the H—C and H—N atoms, eight have been found to be shorter than the sum of van der Waals radii. The analysis of contacts on the Hirshfeld surface reveals that the H—NÁ Á ÁCl hydrogen bonds are enriched (over-represented) and act as the driving force in the crystal packing formation. The metformin cations form favorable electrostatic interactions with the chloride anions which have globally a stronger energy than the unfavorable cation/cation interactions.</p>
            </abstract>
          </profileDesc>
        </biblFull>
      </listBibl>
    </body>
    <back>
      <listOrg type="structures">
        <org type="institution" xml:id="struct-491367" status="INCOMING">
          <orgName>The American College, Madurai</orgName>
          <desc>
            <address>
              <addrLine>625002, Tamilnadu</addrLine>
              <country key="IN"/>
            </address>
          </desc>
        </org>
        <org type="laboratory" xml:id="struct-129683" status="VALID">
          <idno type="IdRef">168910233</idno>
          <idno type="ISNI">0000000417587055</idno>
          <idno type="RNSR">200112437U</idno>
          <idno type="IdUnivLorraine">[UL]RPA--</idno>
          <idno type="ROR">https://ror.org/017je3b10</idno>
          <orgName>Cristallographie, Résonance Magnétique et Modélisations</orgName>
          <orgName type="acronym">CRM2</orgName>
          <date type="start">2001-01-01</date>
          <desc>
            <address>
              <addrLine>Université de Lorraine - Faculté des Sciences, boulevard des Aiguillettes, BP 70239, 54506 Vandoeuvre-les-Nancy Cedex</addrLine>
              <country key="FR"/>
            </address>
            <ref type="url">http://crm2.univ-lorraine.fr/</ref>
          </desc>
          <listRelation>
            <relation active="#struct-413289" type="direct"/>
            <relation name="UMR7036" active="#struct-441569" type="direct"/>
          </listRelation>
        </org>
        <org type="institution" xml:id="struct-86671" status="VALID">
          <orgName>Indian Institute of Science [Bangalore]</orgName>
          <orgName type="acronym">IISc Bangalore</orgName>
          <desc>
            <address>
              <addrLine>Bangalore 560 012</addrLine>
              <country key="IN"/>
            </address>
            <ref type="url">http://www.iisc.ernet.in/</ref>
          </desc>
        </org>
        <org type="institution" xml:id="struct-413289" status="VALID">
          <idno type="IdRef">157040569</idno>
          <idno type="IdUnivLorraine">[UL]100--</idno>
          <idno type="ROR">https://ror.org/04vfs2w97</idno>
          <orgName>Université de Lorraine</orgName>
          <orgName type="acronym">UL</orgName>
          <date type="start">2012-01-01</date>
          <desc>
            <address>
              <addrLine>34 cours Léopold - CS 25233 - 54052 Nancy cedex</addrLine>
              <country key="FR"/>
            </address>
            <ref type="url">http://www.univ-lorraine.fr/</ref>
          </desc>
        </org>
        <org type="regroupinstitution" xml:id="struct-441569" status="VALID">
          <idno type="IdRef">02636817X</idno>
          <idno type="ISNI">0000000122597504</idno>
          <idno type="ROR">https://ror.org/02feahw73</idno>
          <orgName>Centre National de la Recherche Scientifique</orgName>
          <orgName type="acronym">CNRS</orgName>
          <date type="start">1939-10-19</date>
          <desc>
            <address>
              <country key="FR"/>
            </address>
            <ref type="url">https://www.cnrs.fr/</ref>
          </desc>
        </org>
      </listOrg>
    </back>
  </text>
</TEI>