Investigation of property prediction for pharmaceutical co-crystals using synchrotron radiation based X-ray study

• Project/Area Number: 26460057
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Physical pharmacy
• Research Institution: Japan Synchrotron Radiation Research Institute
• Principal Investigator: Sugimoto Kunihisa 公益財団法人高輝度光科学研究センター, 利用研究促進部門, 研究員 (00512807)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Project Status: Completed (Fiscal Year 2016)
• Budget Amount: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000); Fiscal Year 2016: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000); Fiscal Year 2015: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000); Fiscal Year 2014: ¥3,250,000 (Direct Cost: ¥2,500,000、Indirect Cost: ¥750,000)
• Keywords: 共結晶体 / 放射光 / 精密構造解析 / 物性予測 / 物性予測制御 / 放射光X線

Outline of Final Research Achievements

Co-crystals of caffeine-oxalic acid and caffeine-malonic acid were synthesized as single crystal. Synchrotron radiation X-ray diffraction experiment (SR-XRD) performed at single crystal analysis beamline BL02B1/SPring-8. The charge density distribution and electrostatic potential map of co-crystals were successfully visualized by charge density study using high-resolution X-ray diffraction data. We elucidate the hydrogen bonding in co-crystal of caffeine-oxalic acid quantitatively stronger than that of caffeine-malonic acid. To directly visualize of intermolecular interaction by charge density study using SR-XRD does not only push the investigation of efficient way of design for pharmaceutical complex, but also contribute to development of functional materials.

Research Products

• [Int'l Joint Research] オーフス大学(デンマーク)
• [Journal Article] Structural characterization of caffeine-oxalic acid co-crystals from the powder diffraction pattern at the SPring-8 BL02B2 beamline (2017)
  • Author(s): K. Sugimoto, S. Kawaguchi, M. Takemoto
  • Journal Title: Powder Diff. Volume: 印刷中 Issue: S1 Pages: S19-S26
  • DOI: 10.1017/s088571561700032x
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Mixed-Valence Nickel Bis(azamacrocycle) Compounds with Ghost-Leg-type Sheets (2017)
  • Author(s): Ryota Hashiguchi, Kazuya Otsubo, Masato Maesato, Kunihisa Sugimoto, Akihiko Fujiwara, Hiroshi Kitagawa
  • Journal Title: Angew. Chem. Int. Ed. Volume: 56 Issue: 14 Pages: 3838-3841
  • DOI: 10.1002/anie.201610515
  • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] Electronic Perturbation of Supramolecular Conjugates of Porphyrins and Phthalocyanines (2017)
  • Author(s): N. Mihara, Y. Yamada, S. Akine, K. Sugimoto, and K. Tanaka
  • Journal Title: Chem. Commun. Volume: 53 Issue: 14 Pages: 2230-2232
  • DOI: 10.1039/c6cc09590a
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Physical properties and crystal structure analysis of double-perovskite NdBaMn2O6 by using single crystals (2017)
  • Author(s): S. Yamada, H. Sagayama, K. Higuchi, T. Sasaki, K. Sugimoto, T. Arima
  • Journal Title: Phys. Rev. B Volume: 95 Issue: 3 Pages: 035101-035101
  • DOI: 10.1103/physrevb.95.035101
  • Peer Reviewed
• [Journal Article] Tunneling Motion and Antiferroelectric Ordering of Lithium Cations Trapped inside Carbon Cages (2016)
  • Author(s): Shinobu Aoyagi, Akio Tokumitu, Kunihisa Sugimoto, Hiroshi Okada, Norihisa Hoshino, and Tomoyuki Akutagawa
  • Journal Title: J. Phys. Soc. Jpn. Volume: 85 Issue: 9 Pages: 094605-094605
  • DOI: 10.7566/jpsj.85.094605
  • NAID: 210000134082
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Carrier concentration dependence of structural disorder in thermoelectric Sn1-xTe (2016)
  • Author(s): M. Sist, E. M. J. Hedegaard, S. Christensen, N. Bindzus, K. F. F. Fischer, H. Kasai, K. Sugimoto, B. B. Iversen
  • Journal Title: IUCrJ Volume: 2 Issue: 5 Pages: 377-388
  • DOI: 10.1107/s2052252516012707
  • NAID: 120007129384
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Time-resolved Crystal Structure Analysis of Resonantly Vibrating Langasite Oscillator (2016)
  • Author(s): S. Aoyagi, H. Osawa, K. Sugimoto, S. Takeda, C. Moriyoshi and Y. Kuroiwa
  • Journal Title: Jpn. J. Appl. Phys. Volume: 55 Issue: 10S Pages: 10TC05-10TC05
  • DOI: 10.7567/jjap.55.10tc05
  • NAID: 210000147184
  • Peer Reviewed / Open Access
• [Journal Article] Structurally Diverse Polynuclear Copper(I) Complexes Bridged by Pyrimidine-, Pyrazine-, and Triazine-based Ligands with Several 2-Pyridyl Groups (2016)
  • Author(s): M. Maekawa, et al.
  • Journal Title: ChemistrySelect Volume: 1 Issue: 13 Pages: 3812-3822
  • DOI: 10.1002/slct.201600791
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Bis(dipyrrinato)zinc(II) Complexes: Emission in the Solid State (2016)
  • Author(s): M. Tsuchiya, R. Sakamoto, M. Shimada, Y. Yamanoi, Y. Hattori, K. Sugimoto, E. Nishibori, H. Nishihara
  • Journal Title: Inorg. Chem. Volume: 55 Issue: 12 Pages: 5732-5734
  • DOI: 10.1021/acs.inorgchem.6b00431
  • Peer Reviewed
• [Journal Article] First-Order Structural Change Accompanied by Yb Valence Transition in YbInCu4 (2016)
  • Author(s): S. Tsutsui, K. Sugimoto, R. Tsunoda, Y. Hirose, T. Mito, R. Settai, M. Mizumaki
  • Journal Title: J. Phys. Soc. Jpn. Volume: 85 Issue: 6 Pages: 063602-063602
  • DOI: 10.7566/jpsj.85.063602
  • NAID: 210000133947
  • Peer Reviewed
• [Journal Article] Ultrafine Metal-Organic Right Square Prism-Shaped Nanowires (2016)
  • Author(s): Ken-ichi Otake, Kazuya Otsubo, Kunihisa Sugimoto, Akihiko Fujiwara, Hiroshi Kitagawa
  • Journal Title: Angew. Chem. Int. Ed. Volume: 55 Issue: 22 Pages: 6448-6451
  • DOI: 10.1002/anie.201601678
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Correlation of superconductivity with crystal structure in (NH3)yCsxFeSe (2016)
  • Author(s): Lu Zheng, Xiao Miao, Yusuke Sakai, Hidenori Goto, Eri Uesugi, Ritsuko Eguchi, Saki Nishiyama, Kunihisa Sugimoto, Akihiko Fujiwara and Yoshihiro Kubozono
  • Journal Title: Phys. Rev. B Volume: 93 Issue: 10 Pages: 104508-104508
  • DOI: 10.1103/physrevb.93.104508
  • NAID: 120006382537
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Neutral-Type One-Dimensional Mixed-Valence Halogen-Bridged Platinum Chain Complexes with Large Charge-Transfer Band Gaps (2016)
  • Author(s): Ken-ichi Otake, Kazuya Otsubo, Kunihisa Sugimoto, Akihiko Fujiwara, Hiroshi Kitagawa
  • Journal Title: Inorg. Chem. Volume: 55 Issue: 5 Pages: 2620-2626
  • DOI: 10.1021/acs.inorgchem.5b02980
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Heterometallic Ag(I)-Ir(III) hydride coordination polymers bridged by Ir(III) metalloligands (2016)
  • Author(s): M. Maekawa, Y. Kubo, K. Sugimoto, Takashi Okubo, T. Kuroda-Sowa and M. Munakata
  • Journal Title: European Journal of Inorganic Chemistry Volume: (1) Issue: 1 Pages: 78-91
  • DOI: 10.1002/ejic.201500996
  • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
• [Journal Article] Water-triggered macroscopic structural transformation of a metal-organic framework (2016)
  • Author(s): M. Ohtani, K. Takase, P. Wang, K. Higashi, K. Ueno, N. Yasuda, K. Sugimoto, M. Furuta, K. Kobiro
  • Journal Title: CrystEngComm Volume: 18 Issue: 11 Pages: 1866-1870
  • DOI: 10.1039/c6ce00031b
  • Peer Reviewed
• [Journal Article] Kinetically "locked" metallomacrocycle (2016)
  • Author(s): T. Nishino, Y. Yamada, S. Akine, K. Sugimoto, K. Tanaka
  • Journal Title: Dalton Trans. Volume: 45 Issue: 9 Pages: 3831-3837
  • DOI: 10.1039/c5dt04635a
  • Peer Reviewed
• [Journal Article] Orthorhombic distortion and orbital order in the vanadium spinel FeV2O4 (2016)
  • Author(s): S. Kawaguchi, H. Ishibashi, S. Nishihara, S. Mori, J. Campo, F. Porcher, O. Fabelo, K. Sugimoto, J. Kim, K. Kato, M. Takata, H. Nakao, Y. Kubota
  • Journal Title: Phys. Rev. B Volume: 93 Issue: 2 Pages: 3831-3837
  • DOI: 10.1103/physrevb.93.024108
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Bright Solid-State Emission of Disilane-Bridged Donor-Acceptor-Donor and Acceptor-Donor-Acceptor Chromophores (2016)
  • Author(s): M. Shimada, M. Tsuchiya, R. Sakamoto, Y. Yamanoi, E. Nishibori, K. Sugimoto, H. Nishihara
  • Journal Title: Angew. Chem. Int. Ed. Volume: 55 Issue: 9 Pages: 3022-3026
  • DOI: 10.1002/anie.201509380
  • Peer Reviewed
• [Journal Article] Fluorescence and phosphorescence of a series of silicon-containing six-membered-ring molecules (2016)
  • Author(s): T. Nakashima, M. Shimada, Y. Kurihara, M. Tsuchiya, Y. Yamanoi, E. Nishibori, K. Sugimoto, H. Nishihara
  • Journal Title: J. Organomet. Chem. Volume: 805 Pages: 27-33
  • DOI: 10.1016/j.jorganchem.2015.12.042
  • Peer Reviewed
• [Journal Article] Quantitative analysis of intermolecular interactions in orthorhombic rubrene (2015)
  • Author(s): V. R. Hathwar, M. Sist, M. R. V. Jorgensen, A. H. Mamakhel, X. Wang, C. M. Hoffmann, K. Sugimoto, J. Overgaarda, B. Iversen
  • Journal Title: IUCrJ Volume: 2 Issue: 5 Pages: 563-574
  • DOI: 10.1107/s2052252515012130
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Bis(dipyrrinato)metal(II) coordination polymers: Crystallization, exfoliation into single wires, and electric conversion ability (2015)
  • Author(s): Ryota Matsuoka, Ryojun Toyoda, Ryota Sakamoto, Mizuho Tsuchiya, Ken Hoshiko, Tatsuhiro Nagayama, Yoshiyuki Nonoguchi, Kunihisa Sugimoto, Eiji Nishibori, Tsuyoshi Kawai, Hiroshi Nishihara
  • Journal Title: Chemical Science Volume: in press Issue: 5 Pages: 2853-2858
  • DOI: 10.1039/c5sc00273g
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] Optical Properties of Disilane-Bridged Donor Acceptor Architectures: Strong Effect of Substituents on Fluorescence and Nonlinear Optical Properties (2015)
  • Author(s): M. Shimada, Y. Yamanoi, T. Matsushita, T. Kondo, E. Nishibori, A. Hatakeyama, K. Sugimoto, H. Nishihara
  • Journal Title: Journal of the American Chemical Society Volume: 137 Issue: 3 Pages: 1024-1027
  • DOI: 10.1021/ja511177e
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] A compact planar low-energy-gap molecule with a donor-acceptor-donor nature based on a bimetal dithiolene complex (2015)
  • Author(s): M. Hayashi, K. Otsubo, T. Kato, K. Sugimoto, A. Fujiwara, H. Kitagawa
  • Journal Title: Chem. Commun. Volume: 51 Issue: 87 Pages: 15796-15799
  • DOI: 10.1039/c5cc06149k
  • NAID: 120005698011
  • Peer Reviewed / Open Access
• [Journal Article] Atomic motion of resonantly vibrating quartz crystal visualized by time-resolved X-ray diffraction (2015)
  • Author(s): S. Aoyagi, H. Osawa, K. Sugimoto, A. Fujiwara, S. Takeda, C, Moriyoshi, Y. Kuroiwa
  • Journal Title: Appl. Phys. Lett. Volume: 107 Issue: 20 Pages: 201905-201905
  • DOI: 10.1063/1.4935591
  • Peer Reviewed
• [Journal Article] Thermally, Operationally, and Environmentally Stable Organic Thin-Film Transistors Based on Bis[1]benzothieno[2,3-d:2 ',3 '-d ']naphtho[2,3-b:6,7-b ']dithiophene Derivatives: Effective Synthesis, Electronic Structures, and Structure-Property Relationship (2015)
  • Author(s): M. Abe, T. Mori, I. Osaka, K. Sugimoto, K. Takimiya
  • Journal Title: Chem. Mater. Volume: 27 Issue: 14 Pages: 5049-5057
  • DOI: 10.1021/acs.chemmater.5b01608
  • Peer Reviewed / Open Access
• [Journal Article] Dinuclear and polymeric copper(I) ethylene adducts bridged by bis-pyridyl derivatives of 1,2,4-triazole and 1,2,4,5-tetrazine (2015)
  • Author(s): M. Maekawa, K. Sugimoto, T. Okubo, T. Kuroda-Sowa, M. Munakata
  • Journal Title: Inorganica Chimica Acta Volume: 426 Pages: 64-70
  • DOI: 10.1016/j.ica.2014.10.028
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Porous coordination polymers with ubiquitous and biocompatible metals and a neutral bridging ligand (2015)
  • Author(s): Shin-ichiro Noro, Junya Mizutani, Yuh Hijikata, Ryotaro Matsuda, Hiroshi Sato, Susumu Kitagawa, Kunihisa Sugimoto, Yasutaka Inubushi, Kazuya Kubo, and Takayoshi Nakamura
  • Journal Title: Nature Communications Volume: 6 Issue: 1 Pages: 5851-5851
  • DOI: 10.1038/ncomms6851
  • NAID: 120005745622
  • Peer Reviewed / Open Access / Acknowledgement Compliant
• [Journal Article] A Ferromagnetically Coupled Fe42 Cyanide-Bridged Nanocage (2015)
  • Author(s): S. Kang, H. Zheng, T. Liu, K. Hamachi, S. Kanegawa, K. Sugimoto, Y. Shiota, S. Hayami, M. Mito, T. Nakamura, M. Nakano, M. Baker, H. Nojiri, K. Yoshizawa, C. Duan, and O. Sato
  • Journal Title: Nature Communications Volume: 6 Issue: 1 Pages: 5955-5955
  • DOI: 10.1038/ncomms6955
  • Peer Reviewed / Open Access
• [Journal Article] Advanced Crystal Structure Analysis Using Synchrotron X-ray Radiation (2014)
  • Author(s): 杉本邦久
  • Journal Title: Nihon Kessho Gakkaishi Volume: 56 Issue: 5 Pages: 296-300
  • DOI: 10.5940/jcrsj.56.296
  • NAID: 130004714198
  • ISSN: 0369-4585, 1884-5576
  • Peer Reviewed / Open Access
• [Journal Article] Anomalous x-ray scattering studies of functional disordered materials (2014)
  • Author(s): S. Kohara, H. Tajiri, C. H. Song, K. Ohara, L. Temleitner, K. Sugimito, A. Fujiwara, L. Pusztai, T. Usuki, S. Hosokawa, Y. Benino, N. Kitamura and K. Fukumi
  • Journal Title: Journal of Physics: Conference Series Volume: 502 Pages: 12014-6
  • DOI: 10.1088/1742-6596/502/1/012014
  • NAID: 120006697190
  • Peer Reviewed
• [Journal Article] “Structure of Tm2 and Tm2C2 Encapsulated in Low Symmetry C82(Cs(6)) Fullerene Cage by Single Crystal X-ray Diffraction” (2014)
  • Author(s): Y.Sado
  • Journal Title: Chem.Phys.Lett. Volume: 600 Pages: 38-42
  • DOI: 10.1016/j.cplett.2014.03.047
  • Peer Reviewed
• [Journal Article] Evidence of electronic polarization of the As ion in the superconducting phase of F-doped LaFeAsO (2014)
  • Author(s): J. Kim, A. Fujiwara, T. Sawada, Y. Kim, K. Sugimoto, K. Kato, H. Tanaka, M. Ishikado, S. Shamoto, and M. Takata
  • Journal Title: IUCrJ Volume: 1-3 Issue: 3 Pages: 155-159
  • DOI: 10.1107/s2052252514005636
  • Peer Reviewed
• [Journal Article] Hierarchical Dielectric Orders in Layered Ferroelectrics Bi_2SiO_5 (2014)
  • Author(s): Younghun Kim, Jungeun Kim, Akihiko Fujiwara, Hiroki Taniguchi, Sungwng Kim, Hiroshi Tanaka, Kunihisa Sugimoto, Kenichi Kato, Mitsuru Itoh, Hideo Hosono, and Masaki Takata
  • Journal Title: IUCrJ Volume: vol.1 Issue: 3 Pages: 160-164
  • DOI: 10.1107/s2052252514008008
  • Peer Reviewed
• [Journal Article] Crystal Structures of Stacked Ionic Assemblies of Tetracationic and Tetraanionic Porphyrins (2014)
  • Author(s): Yamada, Y.; Matsumoto, S.; Yamada, K.; Nishino, T.; Mihara, N.; Sugimoto, K.; Tanaka, K.
  • Journal Title: Chemistry Letters Volume: 43 Issue: 8 Pages: 1377-1379
  • DOI: 10.1246/cl.140392
  • NAID: 130004677574
  • Peer Reviewed
• [Journal Article] Hirshfeld atom refinement for modelling strong hydrogen bonds. (2014)
  • Author(s): M. Woinska, D. Jayatilaka, M. A. Spackman, A. J. Edwards, P. M. Dominiak, K. Wozniak, E. Nishibori, K. Sugimoto and S. Grabowsky
  • Journal Title: Acta Cryst. Volume: A70 Issue: 5 Pages: 483-498
  • DOI: 10.1107/s2053273314012443
  • Peer Reviewed
• [Presentation] Controlled Self-Assembly of a 2-D Sheet Coordination Polymer and Monomer Containing Eight-Membered Cu4I4 Ring Crown Motif (2016)
  • Author(s): Kunihisa Sugimoto, Masahiko Maekawa, Takayoshi Kuroda-Sowa
  • Organizer: The 14th Conference of the Asian Crystallographic Association (AsCA2016)
  • Place of Presentation: Hanoi, Vietnam
  • Year and Date: 2016-12-04
  • Int'l Joint Research
• [Presentation] 八員環Cu4I4クラウンモチーフを有する金属錯体の結晶構造 (2016)
  • Author(s): 杉本邦久、前川雅彦、黒田孝義
  • Organizer: 平成28年度日本結晶学会年会
  • Place of Presentation: 茨城県立県民文化センター（茨城県水戸市）
  • Year and Date: 2016-11-17
• [Presentation] 先端放射光で物質の成り立ちを探究する (2016)
  • Author(s): 杉本邦久
  • Organizer: 第6回CSJ化学フェスタ2016
  • Place of Presentation: タワーホール船堀（東京都江戸川区）
  • Year and Date: 2016-11-14
• [Presentation] Structural characterization of co-crystal caffeine with dicarboxylic acid from powder diffraction (2016)
  • Author(s): Kunihisa Sugimoto, Syogo Kawaguchi, Michitaka Takemoto
  • Organizer: 15th European Powder Diffraction Conference
  • Place of Presentation: Bari, Italy
  • Year and Date: 2016-06-12
  • Int'l Joint Research
• [Presentation] Crystal engineering of cocrystals: air-stable cyclohexasulfur as cocrystal (2015)
  • Author(s): Kunihisa Sugimoto
  • Organizer: The Collaborative Conference on Crystal Growth
  • Place of Presentation: Hong Kong, Chaina
  • Year and Date: 2015-12-14
  • Int'l Joint Research / Invited
• [Presentation] 先端放射光SPring-8で物質機能の起源を解き明かす (2015)
  • Author(s): 杉本邦久
  • Organizer: 第5回CSJ化学フェスタ2015
  • Place of Presentation: タワーホール船堀（東京都江戸川区）
  • Year and Date: 2015-10-13
  • Invited
• [Presentation] 放射光X線による構造解析の現状と将来 (2014)
  • Author(s): 杉本邦久
  • Organizer: 日本結晶学会年会
  • Place of Presentation: 東京大学本郷キャンパス（東京都文京区）
  • Year and Date: 2014-11-01 – 2014-11-03
  • Invited
• [Presentation] Direct Visualization of Energy-transferred Excited State in Europium Complex with a Single Helical Ligand (2014)
  • Author(s): Kunihisa Sugimoto, Akihiko Fujiwara, Masaki Takata, Hiroshi Tanaka, Miki Hasegawa
  • Organizer: International Union of Materials Research Societies, International Conference in Asia
  • Place of Presentation: 福岡大学七隈キャンパス（福岡県福岡市）
  • Year and Date: 2014-08-24 – 2014-08-28
• [Presentation] Direct Visualization of Energy-transferred Excited State in Eu Complex (2014)
  • Author(s): Kunihisa Sugimoto, Akihiko Fujiwara, Masaki Takata, Hiroshi Tanaka, Miki Hasegawa
  • Organizer: XXIII Congress and General Assembly, International Union of Crystallography
  • Place of Presentation: Montreal, Canada
  • Year and Date: 2014-08-05 – 2014-08-12
• [Remarks] SPring-8/JASRI利用研究促進部門
  • URL: http://rud.spring8.or.jp/member/0006544.html
• [Remarks] 高輝度光科学研究センター・利用研究促進部門・メンバー
  • URL: http://rud.spring8.or.jp/member/0006544.html
• [Remarks] SPring-8 Web site・メンバーデータ
  • URL: http://www.spring8.or.jp/ja/memberdata/mdataview?id=141065
• [Remarks] 杉本 邦久さんのプロフィール
  • URL: http://www.spring8.or.jp/ja/memberdata/06544