Home Crystal structure of 2-bromo-1,3,6,8-tetramethylBOPHY (BOPHY = bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine), C14H15B2BrF4N4
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Crystal structure of 2-bromo-1,3,6,8-tetramethylBOPHY (BOPHY = bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine), C14H15B2BrF4N4

  • Weifeng He , Yingfan Liu EMAIL logo , Saisai Sun , Guangqian Ji and Xiaochuan Li ORCID logo EMAIL logo
Published/Copyright: June 21, 2021
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 236 Issue 5

Abstract

C14H15B2BrF4N4, orthorhombic, Pbca (no. 61), a = 11.970(1) Å, b = 10.049(1) Å, c = 27.847(1) Å, V = 3349.6 Å3, Z = 8, R gt(F) = 0.0697, wR ref(F 2) = 0.1585, T = 296 K.

CCDC no.: 2080820

The molecular structure is shown in Figure 1. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Figure 1: A view of the molecule. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
Figure 1:

A view of the molecule. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.

Table 1:

Data collection and handling.
Crystal: Yellow block
Size: 0.30 × 0.23 × 0.17 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 2.50 mm−1
Diffractometer, scan mode: Xcalibur, φ and ω
θ max, completeness: 28.3°, >99%
N(hkl)measured, N(hkl)unique, R int: 66,122, 4156, 0.088
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 2757
N(param)refined: 240
Programs: CrysAlis PRO [1], Olex2 [2], Shelx [3], [4], Diamond [5]
Table 2:

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

Atom x y z U iso*/U eq
Br1a 0.88323 (7) 0.11819 (9) 0.32237 (3) 0.0583 (3)
Br1Ab 0.8956 (2) 0.1305 (3) 0.77722 (7) 0.0749 (9)
F1 0.7733 (3) −0.1147 (3) 0.51179 (10) 0.0497 (7)
F2 0.6626 (2) 0.0665 (3) 0.50726 (11) 0.0519 (8)
F3 1.0896 (2) 0.2477 (3) 0.59149 (11) 0.0522 (8)
F4 0.9340 (3) 0.3742 (3) 0.59566 (11) 0.0545 (8)
N1 0.8334 (3) 0.0671 (4) 0.46243 (14) 0.0373 (9)
N2 0.8341 (3) 0.0834 (4) 0.55227 (14) 0.0354 (9)
N3 0.9272 (3) 0.1692 (4) 0.55015 (14) 0.0351 (8)
N4 0.9367 (3) 0.1716 (4) 0.64030 (14) 0.0407 (9)
C1 0.9624 (4) 0.1770 (5) 0.41647 (18) 0.0395 (11)
C2 0.8877 (4) 0.1092 (5) 0.38792 (17) 0.0426 (11)
H2b 0.889841 0.107987 0.354539 0.051*
C3 0.8084 (4) 0.0426 (5) 0.41569 (17) 0.0385 (11)
C4 0.9268 (4) 0.1487 (4) 0.46382 (16) 0.0354 (10)
C5 0.9678 (4) 0.1967 (4) 0.50714 (18) 0.0386 (11)
H5 1.029286 0.253244 0.505775 0.046*
C6 0.7992 (4) 0.0483 (5) 0.59532 (17) 0.0387 (11)
H6 0.737803 −0.008248 0.596666 0.046*
C7 0.8447 (4) 0.0871 (5) 0.63847 (17) 0.0402 (11)
C8 0.9656 (5) 0.1867 (6) 0.68679 (19) 0.0504 (13)
C9 0.8910 (6) 0.1140 (6) 0.7155 (2) 0.0624 (16)
H9a 0.892074 0.110233 0.748832 0.075*
C10 0.8163 (5) 0.0495 (6) 0.6863 (2) 0.0532 (14)
C11 0.7241 (6) −0.0427 (8) 0.7002 (2) 0.081 (2)
H11A 0.653595 0.001763 0.696621 0.122*
H11B 0.733569 −0.069270 0.733096 0.122*
H11C 0.725754 −0.119962 0.679961 0.122*
C12 0.7139 (4) −0.0415 (5) 0.40104 (19) 0.0490 (13)
H12A 0.714879 −0.122735 0.419146 0.074*
H12B 0.719844 −0.061425 0.367423 0.074*
H12C 0.645116 0.004912 0.406976 0.074*
C13 1.0568 (4) 0.2623 (6) 0.40167 (19) 0.0520 (13)
H13A 1.117360 0.251840 0.423967 0.078*
H13B 1.033305 0.353636 0.401287 0.078*
H13C 1.081203 0.236908 0.370127 0.078*
C14 1.0607 (5) 0.2729 (7) 0.7020 (2) 0.076 (2)
H14A 1.050319 0.360990 0.689408 0.113*
H14B 1.129352 0.236601 0.689836 0.113*
H14C 1.063735 0.276505 0.736381 0.113*
B1 0.7705 (4) 0.0220 (5) 0.5066 (2) 0.0378 (12)
B2 0.9757 (4) 0.2453 (6) 0.5953 (2) 0.0385 (12)

  1. aOccupancy: 0.7049(17), bOccupancy: 0.2951(17).

Source of material

2-Bromo-1,3,6,8-tetramethylBOPHY was synthesized according to the literature [6], [7], [8], [9]. Firstly, 2,4-dimethylpyrrole and boron trifluoride etherate were condensed at room temperature to give 1,3,6,8-tetram-ethylBOPHY [6], [7]. Next, bromination of 1,3,6,8-tetramethyl-BOPHY would give single or double bromine substituted BOPHY derivatives by treating it with a halogenation reagent. Copper(II) bromide and N-bromosuccinimide (NBS) are all candidates for bromination of 1,3,6,8-tetramethylBOPHY. However, bromination with NBS is an economic selection, together with the advantage of an easier work-up and purification. Additionally, there are two β positions, where both the two aromatic hydrogen atoms are easy to be substituted by halogenation when subject to electrophilic attack of electrophiles. In case of bromination of 1,3,6,8-tetramethylBOPHY, the mono-bromination is strongly dependent on the equivalent proportion between 1,3,6,8-tetramethylBOPHY and NBS. When treated with one equivalent of NBS, mono-bromo derivatives will be the main product, together with a small quantity of di-bromo derivatives. 1,3,6,8-tetramethyl-BOPHY (338 mg) was added to dichloromethane (100 mL) and stirred until a complete dissolution. NBS (178 mg) was added in portions to the above solution at room temperature. The mixture was stirred for about 12 h in the dark. Reaction progress was monitored by TLC methodology. Once BOPHY disappeared in the TLC plate, the mixture was quenched by distilled water (100 mL). After successive extraction, washing, drying, and condensing, the crude product was purified by silica gel column chromatography, yielding an orange powder (186 mg). Single crystals suitable for X-ray diffraction were obtained by evaporation of a saturated dichloromethane solution of the obtained orange powder within five days.

Experimental details

The hydrogen atoms were placed geometrically and refined using a riding model with d (C–H) = 0.93 Å (aromatic), 0.96 Å (–CH3). U iso(H) = 1.2 U eq(C) for CH or U iso(H) = 1.5 U eq(C) CH3 groups. There is a disorder at the C2/C9 position (see the figure).

Comment

In dye chemistry, fluorine-boron complex (FBC) is a typical member of fluorescent dyes [8], [9], [10], [11], [12], [13]. It is robust towards light and thermal influences. And its emission in full width at half maximum is narrower than most established fluorescent dyes, such as coumarin, rhodamine, naphthalimide, etc. In the FBC family, the typical one is BODIPY with the emission peak in the green region, which is different from the emission of general FBC [8]. Structurally, BOPHY is similar to BODIPY. Both of them have a BF2 unit. However, BOPHY has two BF2 units. Interestingly, the emission of BOPHY shifts towards shorter wavelength in contrast to BODIPY and one can observe bright blue-green color when excited the BOPHY derivatives in organic solvent. The chemical modification of BOPHY could alter its photophysical properties as expected. More functional groups also can be attached to the BOPHY according to the requirement of material chemistry or biotechnology demand [10], [11], [12], [13], [14], [15]. The substitution strategy of BOPHY can be copied based on that of BODIPY [14], [15]. For example, the sensor configuration of BODIPY can be transferred to BOPHY due to the identical key active position, two β hydrogen atoms and four methyl hydrogen atoms [16], [17]. Therefore, the bromine or iodine substituted BOPHY will be the key compound for the next step of advanced functionalities by copying BODIPY or introducing new groups [18], [19].

There is one molecule in the asymmetric unit. Bond lengths and angles within molecules are in the expected ranges. The frame work of BOPHY is rigid with two pyrrole rings at the periphery, which is identical to that of BODIPY. The difference to BODIPY is that the two pyrrole rings are bridged by hydrazine. The BF2 units fix the molecule to form a closed rigid ring. Therefore, double five and six membered rings configure the basic framework of BOPHY. Also, there is an inversion center (C2h symmetry), following that of BODIPY. The bonds length demonstrates furtherly the regular aromaticity of the pyrrole rings. The ring of BOPHY is coplanar (RMS deviation = 0.102 Å), except the four fluorine atoms. The two plane configured by BF2 units are perpendicular to the tetracyclic system and the dihedral angles are estimated to be 87.74° and 87.73°. The C–N (1.317, 1.322 Å) and N=N (1.410 Å) show a single and double bond character, respectively. Therefore, the conjugate system does not distribute over the whole ring. The β-substituted bromine atoms are disordered and modeled in a 70.5:29.5 ratio.

The intermolecular interactions that drive the crystallization of the dye molecules mainly include C–H⋯F and π⋯π interactions. The parallel staggered molecules are packed by intermolecular π⋯π interactions. The distance between parallel molecules is estimated to be 3.59 Å. Also, many weak C–H⋯π interactions contribute to the cohesion of molecules [20]. Adjacent molecules are connected via non-classical C–H⋯F and C–H⋯Br hydrogen bonds. Each methyl group donates one hydrogen bonds and each bromine atom accepts one of them. All Br⋯H distances are significantly below the typical van der Waals distances [21]. In contrast, each fluorine atom accepts at least one hydrogen bond. More importantly, the C–H⋯F hydrogen bonds are the stronger interactions, which stabilize the dye molecules packing. In addition, the C–H⋯F connect the molecules to zig–zag-chains along the crystallographic c axis. Whereas, the C–H⋯Br connect the molecules side by side linearly. Generally, the tight packing in the solid would lead to significant emission quench. However, some BODIPY or BOPHY emit bright light in solid. Therefore, careful analysis of the intermolecular interactions benefit to understand the aggregated induced emission [8], [9].

Corresponding authors: Yingfan Liu, College of Material and Chemical Engineering, Zhengzhou University of Light Industry, Henan Provincial Key Lab of Surface and Interface Science, Zhengzhou 450002, P. R. China; and Xiaochuan Li, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, P. R. China, E-mail: (Y. Liu), (X. Li)

Funding source: National Natural Science Foundation of China 10.13039/501100001809

Award Identifier / Grant number: 21772034

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

  2. Research funding: This work was supported by the National Natural Science Foundation of China (21772034).

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

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Received: 2021-04-26
Accepted: 2021-05-17
Published Online: 2021-06-21
Published in Print: 2021-09-27

© 2021 Weifeng He et al., published by De Gruyter, Berlin/Boston

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

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  46. The crystal structure of 5-benzoyl-1-[(E)-(4-fluorobenzylidene)amino]-4-phenylpyrimidin-2(1H)-one, C24H16FN3O2
  47. Crystal structure of monocarbonyl(N-nitroso-N-oxido-phenylamine-κ 2 O,O′)(tricyclohexylphosphine-κP)rhodium(I), C25H39N2O3PRh
  48. Crystal structure of poly[bis[μ3-1,3,5-tris[(1H-imidazol-1-yl)methyl]benzene-κ3N:N′:N″]nickel(II)] hexafluorosilicate, C36H36N12NiSiF6
  49. The crystal structure of 13-(pyrazole-1-yl-4-carbonitrile)-matrine, C19H25N5O
  50. Crystal structure of 3,5-bis((E)-4-methoxy-2-(trifluoromethyl)benzylidene)-1-methylpiperidin-4-one, C24H21F6NO3
  51. The crystal structure of N,N′-(Disulfanediyldi-2,1-phenylene)di(6′-methylpyridine)-2-carboxamide, C26H22N4O2S2
  52. Crystal structure of (E)-7-fluoro-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  53. Crystal structure of ethyl 1-(4-fluorophenyl)-4-phenyl-1H-pyrrole-3-carboxylate, C19H16FNO2
  54. The crystal structure of cis-diaqua-bis (N-butyl-N-(pyridin-2-yl)pyridin-2-amine-κ2N,N′)cobalt(II)] dichloride trihydrate, C28H44Cl2N6O5Co
  55. Crystal structure of (E)-7-methoxy-2-((6-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C18H17NO3
  56. Crystal structure of (E)-2-((3-fluoropyridin-4-yl)methylene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  57. The crystal structure of 6-bromohexanoic acid, C6H11BrO2
  58. The crystal structure of 4-chloro-thiophenol, C6H5ClS
  59. The crystal structure of 4-bromobenzyl chloride, C7H6BrCl
  60. The crystal structure of di-tert-butyl dicarbonate, C10H18O5
  61. The crystal structure of (2-(4-chlorophenyl)-5-methyl-1,3-dioxan-5-yl)methanol, C12H15ClO3
  62. The crystal structure of the co-crystal: 2-hydroxybenzoic acid – N′-(butan-2-ylidene)pyridine-4-carbohydrazide, C10H13N3O·C7H6O3
  63. Crystal structure and anti-inflammatory activity of (E)-7-fluoro-2-((5-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  64. Crystal structure of (E)-7-fluoro-2-((6-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  65. Crystal structure of 1,1′-(butane-1,4-diyl)bis(3-propyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C32H56F24N8P4
  66. The crystal structure of dichlorido-bis(3-methyl-3-imidazolium-1-ylpropionato-κ2)-cadmium(II), C14H20CdCl2N4O4
  67. Crystal structure of 1-(2-cyanobenzyl)-3-cyano-4-phenyl-4-(2-cyanobenzyl)-1,4-dihydropyridine monohydrate, C56H42N8O
  68. The crystal structure of 3-(carboxymethyl)-1-ethenyl-1H-imidazol-3-ium chloride, C7H9N2O2Cl
  69. The crystal structure of adamantylmethoxydiphenylsilane, C23H28OSi
  70. Redetermination of the crystal structure of (2E,4Z,13E,15Z)-3,5,14,16-tetramethyl-2,6,13,17-tetraazatricyclo[16.4.0.07,12]docosa-1(22),2,4,7,9,11,13,15,18,20-decaene, C22H24N4
  71. Crystal structure of (E)-7-hydroxy-2-((6-methoxypyridin-2-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H15NO3
  72. Crystal structure of catena-poly[diaqua-bis(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2 N:N′)cobalt(II)] dinitrate, C18H28N10O8Co
https://doi.org/10.1515/ncrs-2021-0163
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of [aqua-(4-iodopyridine-2,6-dicarboxylato-κ3 O,N,O′)-(1,10-phenanothroline-κ2 N,N′)copper(II)] dihydrate, C19H16O7N3CuI
  4. The crystal structure of tetrakis(1-isopropyl-1H-imidazolium) octamolybdate, C24H44Mo8N8O26
  5. Crystal structure of catena-poly[bis(µ2-3,5-bis(1-imidazolyl)pyridine-κ2 N:N′)-(µ2-3-nitrophthalato-k3 O,O′:O″)cadmium(II)] dihydrate, C30H25N11O8Cd
  6. The crystal structure of diaqua-bis(2-(3-(1H-pyrazol-4-yl)-1H-1,2,4-triazol-5-yl)pyridine-κ2 N:N′)-bis(3,5-dicarboxybenzoato-κ1 O)cobalt(II), C38H30CoN12O14
  7. Crystal structure of the nickel(II) complex aqua-(2,6-di(pyrazin-2-yl)-4,4′-bipyridine-κ3 N,N′,N′′)-(phthalato-κ2 O,O′)nickel(II) tetrahydrate, C26H26N6O9Ni
  8. The crystal structure of 1-[5-(2-fluorophenyl)-1-(pyridine-3-sulfonyl)-1H-pyrrol-3-yl]-N-methylmethanaminium 3-carboxyprop-2-enoate, C21H20FN3O6S
  9. The crystal structure of 1,2-bis(4-pyridyl)ethane - 4,4-dihydroxydiphenylmethane (1/1), C25H21N2O2
  10. Crystal structure of bis(2-((E)-5-chloro-2-hydroxybenzylidene)hydrazineyl)methaniminium trifluoroacetate dihydrate, C34H36Cl4N10O12
  11. Crystal structure of 1-cyclopropyl-7-ethoxy-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, C15H13F2NO4
  12. Crystal structure of methyl 3-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)benzoate, C18H15BN2O2
  13. Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-2-hydroxybenzohydrazide, C14H11ClN2O3
  14. Crystal structure of Al-rich fluorophlogopite, K1.0(Mg2.8Al0.2)(Si2.8Al1.2)O10F2
  15. The crystal structure of 4,5-diiodo-1,3-dimesityl-1H-1,2,3-triazol-3-ium hexafluoridoantimonate(V), C20H22F6I2N3Sb
  16. Crystal structure of tris(3-iodopyridin-1-ium) catena-poly[(hexachlorido-κ1 Cl)-(μ2-trichlorido-κ2 Cl:Cl)diantimony(III)], C15H15Cl9I3N3Sb2
  17. Crystal structure of methyl 2-(1H-naphtho[1,8-de][1.3.2]diazaborinin-2(3H-yl)benzoate C18H15BN2O2
  18. The crystal structure of 1,8-bis(4-methoxybenzoyl)naphthalene-2,7-diyl dibenzoate, C40H28O8
  19. Crystal structure of 2-bromo-1,3,6,8-tetramethylBOPHY (BOPHY = bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine), C14H15B2BrF4N4
  20. The crystal structure of (E)-3-chloro-2-(2-(2-fluorobenzylidene)hydrazinyl)pyridine, C12H9ClFN3
  21. Crystal structure of bis(µ2- 4-iodopyridine-2,6-dicarboxylato-κ3O:N:O′)-bis(4-iodopyridine-2,6-dicarboxylato-κ3O:N:O′)-bis(µ2-1-(4-pyridyl)piperazine-κ2N:N′)-hexa-aqua-tetra-copper(II), C46H46Cu4I4N10O22
  22. Crystal structure of poly[diaqua-(μ2-2,5-dihydroxyterephthalato-κ2O:O′)(μ2-bis(4-pyridylformyl)piperazine-κ2N:N′)cadmium(II)] dihydrate, C24H28CdN4O12
  23. Crystal structure of poly[aqua-(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2N:N′)-(μ3-2,3,5,6-tetrafluoroterephthalato-κ3O:O′:O′′)cadmium(II)], C17H14N4O5F4Cd
  24. Crystal structure of 6-(quinolin-8-yl)benzo[a]phenanthridin-5(6H)-one, C26H16N2O
  25. The crystal structure of aqua-bis(6-chloropicolinato-κ2N,O)copper(II), C12H8Cl2N2O5Cu
  26. Crystal structure of catena-poly[diaqua-bis(μ2-4,4′-bipyridyl-κ2N:N′) disilver(I)] 4-oxidopyridine-3-sulfonate trihydrate, C25H29Ag2N5O9S
  27. The crystal structure of 4-(3-bromophenyl)pyrimidin-2-amine, C10H8BrN3
  28. Crystal structure of 6-oxo-4-phenyl-1-propyl-1,6-dihydropyridine-3-carbonitrile, C15H14N2O
  29. Crystal structure of 4-(2,2-difluoroethyl)-2,4-dimethyl-6-(trifluoromethyl)isoquinoline-1,3(2H,4H)-dione, C14H12F5NO2
  30. Crystal structure of dibromido-(1-methyl-1H-imidazole-κ1N)-(3-(3-methyl-1H-imidazol-3-ium-1-yl)propanoato-κ1O)zinc(II), C11H16Br2N4O2Zn
  31. The crystal structure of 1,1′-(((2 (dimethylamino)ethyl)azanediyl)bis(methylene)) bis(naphthalen-2-olato-κ4 N,N′,O,O′)-(pyridine-2,6-dicarboxylato-N,O,O′)- titanium(IV) ─ dichloromethane (2/1), C33H29N3O6Ti
  32. The layered crystal structure of bis(theophyllinium) hexachloridostannate (IV), C14H18N8O8SnCl6
  33. The crystal structre of 3-(1-ethenyl-1H-imidazol-3-ium-3-yl)propane-1-sulfonate, C8H12N2O3S
  34. Synthesis and crystal structure of di-tert-butyl 1″-acetyl-2,2″,9′-trioxo-4a′,9a′-dihydro-1′H,3′H,9′H-dispiro[indoline-3,2′-xanthene-4′,3″-indoline]-1,3′-dicarboxylate, C39H38N2O9
  35. The crystal structure of 4-chloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H9ClN2O2
  36. The crystal structure of 1-fluoro-4-(p-tolylethynyl)benzene, C15H11F
  37. The crystal structure of bis[4-bromo-2-(1H-pyrazol-3-yl) phenolato-κ2N,O] copper(II), C18H12Br2CuN4O2
  38. The crystal structure of poly[(μ 3-imidazolato-κ 3 N:N:N′)(tetrahydrofuran- κ 1 O)lithium(I)], C7H11LiN2O
  39. Crystal structure of N′,N′′′-((1E,1′E)-(propane-2,2-diylbis(1H-pyrrole-5,2diyl))bis(methaneylylidene))di(nicotinohydrazide) pentahydrate, C25H24N8O2·5H2O
  40. Crystal structure of 3-(2-ethoxy-2-oxoethyl)-1-ethyl-1H-imidazol-3-ium hexafluoridophos-phate(V), C9H15F6N2O2P
  41. Crystal structure of (1,10-phenanthroline-κ2N,N′)-bis(3-thiophenecarboxylato-κ2O,O′)copper(II), C22H14N2O4S2Cu
  42. The crystal structure of 2-amino-3-carboxypyridin-1-ium iodide hemihydrate, C6H8IN2O2.5
  43. Crystal structure of (E)-7-methoxy-2-((6-methoxypyridin-2-yl)methylene)-tetralone, C18H17NO3
  44. The crystal structure of [μ-hydroxido-bis[(5,5′-dimethyl-2,2′-bipyridine-κ2N,N′)-tricarbonylrhenium(I)] bromide hemihydrate, C30H26N4O9Re2Br
  45. The crystal structure of 2,5-bis(3,5-dimethylphenyl)thiazolo[5,4-d]thiazole, C20H18N2S2
  46. The crystal structure of 5-benzoyl-1-[(E)-(4-fluorobenzylidene)amino]-4-phenylpyrimidin-2(1H)-one, C24H16FN3O2
  47. Crystal structure of monocarbonyl(N-nitroso-N-oxido-phenylamine-κ 2 O,O′)(tricyclohexylphosphine-κP)rhodium(I), C25H39N2O3PRh
  48. Crystal structure of poly[bis[μ3-1,3,5-tris[(1H-imidazol-1-yl)methyl]benzene-κ3N:N′:N″]nickel(II)] hexafluorosilicate, C36H36N12NiSiF6
  49. The crystal structure of 13-(pyrazole-1-yl-4-carbonitrile)-matrine, C19H25N5O
  50. Crystal structure of 3,5-bis((E)-4-methoxy-2-(trifluoromethyl)benzylidene)-1-methylpiperidin-4-one, C24H21F6NO3
  51. The crystal structure of N,N′-(Disulfanediyldi-2,1-phenylene)di(6′-methylpyridine)-2-carboxamide, C26H22N4O2S2
  52. Crystal structure of (E)-7-fluoro-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C19H14F4O2
  53. Crystal structure of ethyl 1-(4-fluorophenyl)-4-phenyl-1H-pyrrole-3-carboxylate, C19H16FNO2
  54. The crystal structure of cis-diaqua-bis (N-butyl-N-(pyridin-2-yl)pyridin-2-amine-κ2N,N′)cobalt(II)] dichloride trihydrate, C28H44Cl2N6O5Co
  55. Crystal structure of (E)-7-methoxy-2-((6-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C18H17NO3
  56. Crystal structure of (E)-2-((3-fluoropyridin-4-yl)methylene)-7-methoxy-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  57. The crystal structure of 6-bromohexanoic acid, C6H11BrO2
  58. The crystal structure of 4-chloro-thiophenol, C6H5ClS
  59. The crystal structure of 4-bromobenzyl chloride, C7H6BrCl
  60. The crystal structure of di-tert-butyl dicarbonate, C10H18O5
  61. The crystal structure of (2-(4-chlorophenyl)-5-methyl-1,3-dioxan-5-yl)methanol, C12H15ClO3
  62. The crystal structure of the co-crystal: 2-hydroxybenzoic acid – N′-(butan-2-ylidene)pyridine-4-carbohydrazide, C10H13N3O·C7H6O3
  63. Crystal structure and anti-inflammatory activity of (E)-7-fluoro-2-((5-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  64. Crystal structure of (E)-7-fluoro-2-((6-methoxypyridin-3-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H14FNO2
  65. Crystal structure of 1,1′-(butane-1,4-diyl)bis(3-propyl-1H-imidazol-3-ium) bis(hexafluoridophosphate), C32H56F24N8P4
  66. The crystal structure of dichlorido-bis(3-methyl-3-imidazolium-1-ylpropionato-κ2)-cadmium(II), C14H20CdCl2N4O4
  67. Crystal structure of 1-(2-cyanobenzyl)-3-cyano-4-phenyl-4-(2-cyanobenzyl)-1,4-dihydropyridine monohydrate, C56H42N8O
  68. The crystal structure of 3-(carboxymethyl)-1-ethenyl-1H-imidazol-3-ium chloride, C7H9N2O2Cl
  69. The crystal structure of adamantylmethoxydiphenylsilane, C23H28OSi
  70. Redetermination of the crystal structure of (2E,4Z,13E,15Z)-3,5,14,16-tetramethyl-2,6,13,17-tetraazatricyclo[16.4.0.07,12]docosa-1(22),2,4,7,9,11,13,15,18,20-decaene, C22H24N4
  71. Crystal structure of (E)-7-hydroxy-2-((6-methoxypyridin-2-yl)methylene)-3,4-dihydronaphthalen-1(2H)-one, C17H15NO3
  72. Crystal structure of catena-poly[diaqua-bis(μ2-1,3-di(1H-imidazol-1-yl)propane-κ2 N:N′)cobalt(II)] dinitrate, C18H28N10O8Co
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