Bifurcated Halogen Bond-Driven Supramolecular Double Helices from 1,2-Dihalotetrafluorobenzene and 2,2′-Bi(1,8-naphthyridine)
Round 1
Reviewer 1 Report
- line 13: "was difficult to be synthesized" suggest that finally a cocrystal has been obtained which is not the case
- line 95: add reference for CrysAlisPro
- line 96: reference 14 is related to ShelXT, add also the correct reference for Shelx-2014
- line 116: a drawing of the asymmetric unit with thermal ellipsoids is missing, describe in the text the asymmetric unit and the symmetry operations to generate the complete molecules
- line 126: add e.s.d. values to distances
- line 131: a complete table with the crystallographic details is preferred above the short list in the text
- line 138: show the unit cell, add unit of interaction energy in legend
- line 174: add unit of interaction energy in legend
Author Response
Comments and Suggestions for Authors:
- line 13: "was difficult to be synthesized" suggest that finally a cocrystal has been obtained which is not the case
Reply: The author thanks the reviewer very much for helpful comment. "was difficult to be synthesized" has been changed into “was not obtained”.
- line 95: add reference for CrysAlisPro
Reply: The reference for CrysAlisPro has been added.
- line 96: reference 14 is related to ShelXT, add also the correct reference for Shelx-2014
Reply: The correct reference for Shelx-2014 has been added. The author thanks the reviewer very much for helpful suggestions.
- line 116: a drawing of the asymmetric unit with thermal ellipsoids is missing, describe in the text the asymmetric unit and the symmetry operations to generate the complete molecules
Reply: The crystallographic information file of the cocrystal between C6F4I2 and C16H10N4 has been provided as the supplementary material. All these information can be clearly seen in the crystallographic information file.
- line 126: add e.s.d. values to distances
Reply: The ESD values have been added.
- line 131: a complete table with the crystallographic details is preferred above the short list in the text
Reply: Lines 131-137 contain all the crystallographic details. We did not use a table to list these details because there is only one cocrystal.
- line 138: show the unit cell, add unit of interaction energy in legend
Reply: The author thanks the reviewer very much for pointing out this omission. The unit of interaction energy has been added in the legend. The unit cell of the cocrystal has been shown in Figure 3.
- line 174: add unit of interaction energy in legend
Reply: The author thanks the reviewer very much for pointing out this omission. The unit of interaction energy has been added in the legend.
Reviewer 2 Report
In this manuscript, Wang presents co-crystals of 1,2-dihaloperfluorobenzenes and one of binaphthyridine. The idea of this work is really interesting. Commonly, 1,4-dihalogenated perfluorobenzenes are used for halogen bonding-assisted self-assembly, while 1,2-deivatives are less commonly applied for this purpose. The motifs of obtained supramolecualr assosiates is interesting, and the author applied proper theoretical methods for estimation of the energies of non-covalent interactions in crystal and gas phase. This work is an important milestone of the way to optically active XB-based supramolecular associates which can find application in separation, optics etc. Therefore, I recommend acceptance of this work in present form.
My only recommendation is related to references. There are some works on perhalogenated building blocks for XB and their theoretical studies - maybe authors will find them worth being mentioned. This is by no means obligatory; the authors should feel free - if they find them less relevant, the work, in my opinion, should be accepted in present form.
a) 10.1021/acs.cgd.0c01314
b) 10.1134/S0022476622040138
c) 10.3390/cryst10050371
d) 10.1039/c8ce01851k
e) 10.1021/acs.cgd.1c01466
f) 10.1016/j.poly.2021.115644
g) 10.1021/acs.cgd.1c00755
h) 10.1002/anie.202108661
Author Response
Comments and Suggestions for Authors:
In this manuscript, Wang presents co-crystals of 1,2-dihaloperfluorobenzenes and one of binaphthyridine. The idea of this work is really interesting. Commonly, 1,4-dihalogenated perfluorobenzenes are used for halogen bonding-assisted self-assembly, while 1,2-deivatives are less commonly applied for this purpose. The motifs of obtained supramolecualr assosiates is interesting, and the author applied proper theoretical methods for estimation of the energies of non-covalent interactions in crystal and gas phase. This work is an important milestone of the way to optically active XB-based supramolecular associates which can find application in separation, optics etc. Therefore, I recommend acceptance of this work in present form.
My only recommendation is related to references. There are some works on perhalogenated building blocks for XB and their theoretical studies - maybe authors will find them worth being mentioned. This is by no means obligatory; the authors should feel free - if they find them less relevant, the work, in my opinion, should be accepted in present form.
- a) 10.1021/acs.cgd.0c01314
- b) 10.1134/S0022476622040138
- c) 10.3390/cryst10050371
- d) 10.1039/c8ce01851k
- e) 10.1021/acs.cgd.1c01466
- f) 10.1016/j.poly.2021.115644
- g) 10.1021/acs.cgd.1c00755
- h) 10.1002/anie.202108661
Reply: The author thanks the reviewer very much for the positive comments. All these important references have been cited in the paper.
