Startseite The crystal structure of iguratimod-dimethylformamide (1/1), C17H14N2O6S·C3H7NO
Artikel Open Access

The crystal structure of iguratimod-dimethylformamide (1/1), C17H14N2O6S·C3H7NO

  • Wen-Jing Ma ORCID logo , Hao Wang , Zhen-Yu Wang , Yu-Xuan Long , Xin-Qi Wang , Qian Ma , Cui-Ran Xu und Yu-Heng Ma EMAIL logo
Veröffentlicht/Copyright: 5. April 2023

Abstract

C17H14N2O6S·C3H7NO, triclinic, P 1 (no. 2), a = 5.4146(4) Å, b = 11.7925(8) Å, c = 16.9527(12) Å, α = 85.238(2)°, β = 86.674(4)°, γ = 78.959(2)°, V = 1057.77(13) Å3, Z = 2, R gt (F) = 0.0418, wR ref (F 2) = 0.1175, T = 296(2) K.

CCDC no.: 2239925

The asymmetric unit of the title crystal structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Needle
Size: 0.24 × 0.22 × 0.20 mm
Wavelength: Cu Kα radiation (1.54178 Å)
μ: 1.78 mm−1
Diffractometer, scan mode: Bruker APEX-AXS, φ and ω
θ max, completeness: 68.4°, 99%
N(hkl)measured, N(hkl)unique, R int: 24,753, 3854, 0.035
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 3546
N(param)refined: 288
Programs: Bruker [1], Olex2 [2], SHELX [3, 4]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z U iso*/U eq
C1 0.0426 (4) 0.42521 (15) 0.77370 (12) 0.0510 (5)
C2 0.2254 (6) 0.4435 (2) 0.81997 (19) 0.0925 (9)
H2A 0.366857 0.386247 0.829180 0.111*
C3 0.1980 (8) 0.5487 (3) 0.8533 (2) 0.1105 (11)
H3 0.319780 0.561948 0.886072 0.133*
C4 −0.0099 (7) 0.6341 (2) 0.83781 (18) 0.0904 (9)
H4 −0.031668 0.703940 0.861402 0.108*
C5 −0.1779 (6) 0.6155 (2) 0.7891 (2) 0.1015 (10)
H5 −0.314086 0.674260 0.776889 0.122*
C6 −0.1550 (5) 0.5100 (2) 0.75590 (19) 0.0852 (8)
H6 −0.274621 0.498092 0.721811 0.102*
C7 0.2599 (3) 0.27032 (15) 0.69920 (11) 0.0454 (4)
C8 0.4074 (3) 0.33257 (14) 0.65258 (11) 0.0474 (4)
H8 0.373950 0.413004 0.651693 0.057*
C9 0.6091 (3) 0.27654 (14) 0.60597 (10) 0.0421 (4)
C10 0.6438 (3) 0.15677 (14) 0.60668 (10) 0.0439 (4)
C11 0.4935 (3) 0.09182 (14) 0.65300 (11) 0.0455 (4)
H11 0.520180 0.011807 0.650997 0.055*
C12 0.3047 (3) 0.14721 (14) 0.70189 (10) 0.0423 (4)
C13 0.7776 (3) 0.33921 (14) 0.55821 (11) 0.0444 (4)
C14 0.9729 (3) 0.26731 (14) 0.51228 (10) 0.0439 (4)
C15 0.9908 (4) 0.15174 (15) 0.51637 (11) 0.0507 (5)
H15 1.118352 0.108539 0.486260 0.061*
C16 1.3399 (4) 0.27983 (17) 0.42287 (12) 0.0575 (5)
H16 1.436555 0.330208 0.397269 0.069*
C17 0.0927 (4) −0.11520 (18) 0.70668 (13) 0.0596 (5)
H17A 0.172147 −0.094876 0.656775 0.089*
H17B −0.086206 −0.089607 0.704442 0.089*
H17C 0.130014 −0.197737 0.717597 0.089*
C18 −0.3941 (4) 0.1554 (2) 0.89121 (13) 0.0665 (6)
H18 −0.433763 0.092469 0.868432 0.080*
C19 −0.4664 (6) 0.2825 (3) 0.99769 (18) 0.0997 (10)
H19A −0.410290 0.253499 1.049486 0.150*
H19B −0.615328 0.340977 1.002542 0.150*
H19C −0.336438 0.315320 0.968512 0.150*
C20 −0.7255 (6) 0.1334 (4) 0.9900 (2) 0.1188 (12)
H20A −0.882776 0.186642 0.985071 0.178*
H20B −0.698289 0.110485 1.044952 0.178*
H20C −0.729885 0.066215 0.962117 0.178*
N1 0.1510 (3) 0.09013 (12) 0.75419 (9) 0.0497 (4)
H1 0.016179 0.131409 0.773472 0.060*
N2 1.1380 (3) 0.32644 (13) 0.46624 (10) 0.0510 (4)
H2 1.110 (4) 0.398 (2) 0.4685 (14) 0.071 (7)*
N3 −0.5220 (4) 0.18898 (18) 0.95645 (11) 0.0696 (5)
O1 0.0523 (3) 0.31806 (11) 0.74362 (10) 0.0650 (4)
O2 0.7611 (3) 0.44536 (10) 0.55664 (9) 0.0613 (4)
O3 0.8333 (3) 0.09479 (10) 0.56188 (8) 0.0537 (4)
O4 1.4084 (3) 0.17708 (13) 0.41397 (10) 0.0767 (5)
O5 0.0539 (3) −0.06048 (12) 0.85205 (9) 0.0659 (4)
O6 0.4714 (3) −0.08905 (12) 0.78444 (9) 0.0602 (4)
O7 −0.2292 (4) 0.20068 (15) 0.85890 (12) 0.0926 (6)
S1 0.20612 (8) −0.04847 (3) 0.78176 (3) 0.04649 (18)

1 Source of material

In representative experiments, iguratimod was presented by Jiangsu Zhengda Qingjiang Pharmaceutical Co. with no further purification. The iguratimod was dissolved in N,N-dimethylformamide (DMF), and the solution was filtered and placed in a vial, covered with membrane and punctured. The filtrate was slowly evaporated at room temperature to obtain crystals of the title compound.

2 Experimental details

Using Olex2 [2], the structure was solved with the XT [3] structure solution program and refined with the ShelXL [4] refinement package. All H atoms were positioned geometrically and treated as riding on their parent atoms, with the d(C–H) = 0.96 Å (methyl) and d(C–H) = 0.93 Å (aromatic), and U iso(H) = 1.2 times U iso(C) and U iso(H) = 1.5 times U iso(O).

3 Comment

Iguratimod is known for its anti-inflammatory activities and therapeutic effects in patients with rheumatoid arthritis, which can significantly inhibit the initiation and progression of rheumatoid arthritis by regulating T cell differentiation, reducing the production of pro-inflammatory cytokines and immunoglobulins, promoting bone formation, and inhibiting bone resorption [5, 6]. The α and β crystal forms of iguratimod were prepared and five crystal forms of iguratimod were obtained with ethanol, acetonitrile, dimethylformamide, acetone, and dichloromethane [7, 8]. However, the single crystal structure of iguratimod-DMF has not been reported.

The asymmetric unit of the title structure contains one iguratimod molecule and one dimethylformamide molecule (see figure). It indicates that the hydrogen bond plays an important role in maintaining the crystal structure. The O7 atom on the amide group of dimethylformamide is a hydrogen bond acceptor, and the H1 atom on the sulfonamide (N1–H1) of iguratimod is a hydrogen bond donor, forming the intermolecular hydrogen bond N1–H1⋯O7 [length 2.832(2) Å, angle 156.75°]. The O atom on the formamide groups of iguratimod is a hydrogen bond acceptor. The H15 atom on the benzopyran rings (C15–H15) of iguratimod is hydrogen bond donor, forming the intramolecular hydrogen bond C15–H15⋯O4 [length 2.817 Å, angle 125.54°]. The O atom on the formamide groups of iguratimod is a hydrogen bond acceptor. The H15 atom on the benzopyran rings (N2–H2) of iguratimod is hydrogen bond donor, forming the intramolecular hydrogen bond N2–H2⋯O2 [length 2.838(2) Å, angle 147.66°]. All bond lengths and angles are within a reasonable range [9].


Corresponding author: Yu-Heng Ma, School of Materials Science and Chemical Engineering, Chuzhou University, Chuzhou, Anhui, 239000, P.R. China, E-mail:

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: Anhui University Natural Science Foundation-funded project (No. KJ2020B19), New engineering research and reform practice project (2021xgk10), Chuzhou University Initial Funding (2020qd09).

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1. BRUKER. Saint, Apex2 and Sadabs; Bruker AXS Inc.: Madison, Wisconsin, USA, 2009.Suche in Google Scholar

2. Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K., Puschmann, H. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Crystallogr. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Suche in Google Scholar

3. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Suche in Google Scholar

4. Sheldrick, G. M. A short history of SHELXL. Acta Crystallogr. 2008, A64, 112–122; https://doi.org/10.1107/s0108767307043930.Suche in Google Scholar PubMed

5. Xie, S., Li, S., Tian, J., Li, F. Iguratimod as a new drug for rheumatoid arthritis: current landscape. Front. Pharmacol. 2020, 11, 488; https://doi.org/10.3389/fphar.2020.00073.Suche in Google Scholar PubMed PubMed Central

6. Bloom, J., Metz, C., Nalawade, S., Casabar, J., Cheng, K. F., He, M., Sherry, B., Coleman, T., Forsthuber, T., Al-Abed, Y. Identification of iguratimod as an inhibitor of macrophage migration inhibitory factor (MIF) with steroid-sparing potential. J. Biol. Chem. 2016, 291, 26502–26514; https://doi.org/10.1074/jbc.m116.743328.Suche in Google Scholar

7. Liang, Z. X., Mei, L. Y., Wang, X. L., Gao, J. Iguratimod crystalline form and its composition. CN101891726A. 2010-11-17.Suche in Google Scholar

8. Wang, Q. S., Huang, T., Zhang, C., Ping, Q. N. Comparative study on the two crystal forms of iguratimod. J. China Pharm. Univ. 2014, 45, 331–334.Suche in Google Scholar

9. Kuo, P.-Y., Chaung, R.-R., Yang, D.-Y. Reactions of 3-benzoyl-7-dimethylamino-4-hydroxycoumarin and their potential applications in solution- and solid- phase synthesis. Mol. Divers. 2009, 13, 253–260; https://doi.org/10.1007/s11030-009-9107-2.Suche in Google Scholar PubMed

Received: 2023-03-04
Accepted: 2023-03-24
Published Online: 2023-04-05
Published in Print: 2023-06-27

© 2023 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of phenyl(3,3-dichloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one)methanone, C7H4Cl2N2O
  4. Crystal structure of poly[diaqua-bis(μ 2-1,4-diaminobutane-N:N′)cobalt(II)] dichloride, C8H28Cl2CoN4O2
  5. Synthesis and crystal structure of (4aR,7S)-7-hydroxy-7-isopropyl-1,1-dimethyldecahydro-2H,6H-8a,4a-(epoxymethano)phenanthren-12-one, C20H32O3
  6. The crystal structure of 1-(2-chlorobenzyl)-3-(3,5-dichlorophenyl)urea, C14H11Cl3N2O
  7. Crystal structure of tetrapropylammonium-1,3,5-thiadiazole-5-amido-2-carbamate – 1,2,4-thiadiazole-3,5-diamine – water (1/1/1), C17H37N9O3S2
  8. Tetrabutylammonium 1,3,5-thiadiazole-5-amido-2-carbamate—1,2,4-thiadiazole-3,5-diamine— water (1/1/1), C21H45N9O3S2
  9. The crystal structure of ((E)-2,4-dichloro-6-(((2-hydroxy-5-nitrophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Cl2MnN5O4
  10. The crystal structure of aqua-bis{2-bromo-6-((2-(2-phenylacetyl)hydrazineylidene)methyl)phenolato-κ3 N,O,O′}-dimethylformamide-κ1 O-erbium(III) chloride – dimethylformamide – water (1/2/1), C39H49N7O9Br2ClEr
  11. Crystal structure of (diaqua-bis(phenanthroline-K 2 N,N′)-tetrakis(m 2-3,4,5,6-tetrafluorophthalato-K 4 O,O:O′:O″;K 2 O:O′)dierbium (III) phenanthroline (1/2), C80H38Er2F16N8O18
  12. Crystal structure of (E)-7-methoxy-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C20H17F3O3
  13. The crystal structure of 4–(4,4,5,5–tetramethyl–1,3,2–dioxaborolan–2–yl)morpholine, C10H20BNO3
  14. The crystal structure of catena–poly[aqua(1-naphthoato-κ 2 O,O′)-(μ-1-naphthoato-κ 4 O:O,O′:O′)lead(II)], C22H16O5Pb
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  16. The crystal structure of 4-(pyren-1-yl)butyl-4-nitrobenzoate, C27H21NO4
  17. Crystal structure of cyclo-(bis(µ2-3,3′-(1H-imidazole-3-ium-1,3-diyl)dipropionato-κ4 O,O′:O″,O″′)-dinitrato-κ2 O,O′-tetraoxido-diuranium(VI) C18H22N6O18U2
  18. The crystal structure of catena-[nitrato-κ 2 O,O′-(μ 3-3-iodobenzene-1,2-dicarboxylato-κ 4 O:O′:O″,O‴)-(2,2′:6′,2″-terpyridine-κ 3 N,N′,N″)lanthanum(III)], C23H14IN4O7La
  19. Redetermination of crystal structure of [bis(pyridin-2-ylmethyl)amine-κ 3 N,,]chloridopalladium(II) chloride monohydrate
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  21. Crystal structure of trans-diaqua-bis(methyl methylcarbamohydrazonothioato-κ2 N,N′) nickel(II) iodide semihydrate, C6H22N6O2NiS2I2·0.5H2O
  22. The crystal structure of 2-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoindolin-1-one, C17H13F4NOS
  23. The crystal structure of di-μ-1-naphthylacetato-κ 3 O,O′:O;κ 3 O:O,O′-bis[(1-naphthylacetato-κ 2 O,O′)(2,2′-bipyridine-κ 2 N,N′)lead(II)] monohydrate, C68H54N4O9Pb2
  24. Crystal structure of tetrapropylammonium guanidinium 4,4′-sulfonyldibenzoate monohydrate, C27H44N4O7S
  25. Crystal structure of bis(tetrapropylammonium) terephthalate – 1-(diaminomethylene)thiourea – water (1/2/4) C18H40N5O4S
  26. Crystal structure of (E)-7-fluoro-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C21H20FNO2
  27. The crystal structure of poly[diaqua-bis(μ 3-5-bromobenzene-1,3-dicarboxylato-κ 3 O,O,O′)-(μ 2-1,3-bis-(4-pyridyl)-propane-κ 2 N,N′)-dizinc(II))] – 5-bromobenzene-1,3-dicarboxylic acid [2/1], C37H29Br3N2O14Zn2
  28. The crystal structure of 2-bromo-1,3-phenylene bis(4-methylbenzenesulfonate), C20H17BrO6S2
  29. Crystal structure of europium dichromium icosaaluminum, EuCr2Al20
  30. The crystal structure of N1,N3-di((E)-benzylidene) isophthalohydrazide dihydrate, C 22 H 22 N 4 O 4
  31. Crystal structure of 7α,11α-dihydroxy-15-oxo-ent-kauran-16-en-19,6β-olide, C20H26O5
  32. Crystal structure of 4-chloro-N′-[(1E)-pyridin-3-ylmethylidene]benzohydrazide, C13H10ClN3O
  33. The crystal structure of (Z)-3-(1-(2-((E)-4-isopropylbenzylidene)hydrazinyl)ethylidene) chroman-2,4-dione, C21H20N2O3
  34. Crystal structure of E-7-fluoro-2-(2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C18H12F4O
  35. Crystal structure of bis(6-aminopyridine-2-carboxylato–k2O,N)-bis(N,N-dimethylformamide-k1 O)zinc(II), C18H24N6O6Zn
  36. Crystal structure of 5-(adamantan-1-yl)-3-[(4-{[2-(trifluoromethyl)phenyl]-methyl}piperazin-1-yl)methyl]-1,3,4-oxadiazole-2(3H)-thione, C25H31F3N4OS
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  40. The crystal structure of 1-(2-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
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  43. The crystal structure of 4-(4-iodophenyl)-5H-1,2,3-dithiazole-5-thione, C8H4INS3
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  47. Crystal structure of catena-poly[bis(μ2-dicyanamide-κ2 N:N′)-bis(4-vinylpyridine-κN)-copper(II)], C18H14CuN8
  48. The crystal structure of iguratimod-dimethylformamide (1/1), C17H14N2O6S·C3H7NO
  49. Synthesis and crystal structure of 1-((3R,10S,13S,17S)-10,13-dimethyl-3-(m-tolylamino)hexadecahydro-1H-cyclopenta[α]phenanthren-17-yl)ethan-1-one, C28H41NO
  50. The crystal structure of diaqua-bis(4-bromo-2-formylphenoxy)zinc(II), C14H12Br2O6Zn
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  52. The crystal structure of (E)-N′-(1-(4-fluorophenyl)propylidene)-2-hydroxybenzohydrazide, C16H15FN2O2
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