Dicyclohexylammonium O,O’-Diphenyl Phosphate, [(C6H11)2NH2][(C6H5O)2P(O)(O)]: Spectroscopic Study, Crystal Structure, and Hirshfeld Surface Analysis
Round 1
Reviewer 1 Report
The manuscript by Moghaddam et al. nicely describes the structure of an achiral salt which crystalizes in a chiral space group. A complete structural study on the inter e intramolecular interactions are systematically analysed for providing a clear landscape of the crystal energetics. In this issue, different CSD surveys and Hirshfeld surface analysis complete this crystallographic study. The spectroscopic (IR & NMR) and analytic data (m.p. and HRMS) are fully consistent with the proposed structure. Considering everything, I recommend its publication in MolBank after a very minor revision.
- Figures 1, 2, 5-7 seems too large to me. Authors must reduce their size.
- Some figures, e.g., 5 and 7, from the section 2.2 could be moved to the supplementary materials file. Also, the text of this section must be summarised as soon as possible.
- The way for locating the hydrogen atom coordinates must be included.
Author Response
Dear Reviewer,
First of all, thank you very much for reviewing our paper and the time which you spent on. We corrected the paper according to the useful commnets. Details of corrections are as follows:
The manuscript by Moghaddam et al. nicely describes the structure of an achiral salt which crystalizes in a chiral space group. A complete structural study on the inter- and intramolecular interactions are systematically analysed for providing a clear landscape of the crystal energetics. In this issue, different CSD surveys and Hirshfeld surface analysis complete this crystallographic study. The spectroscopic (IR & NMR) and analytic data (m.p. and HRMS) are fully consistent with the proposed structure. Considering everything, I recommend its publication in MolBank after a very minor revision.
Point 1 : Figures 1, 2, 5-7 seems too large to me. Authors must reduce their size.
Response : Figures 1, 2, 5 and 7 sizes are reduced. Other figures also reduced to the similar size.
Point 2 : Some figures, e.g., 5 and 7, from the section 2.2 could be moved to the supplementary materials file. Also, the text of this section must be summarised as soon as possible.
Response : I would be very thankful if you let us keep the figures 5 and 7 in the text, which explain the main text.
Point 3 : The way for locating the hydrogen atom coordinates must be included.
Response : The following text is included in the manuscript section 3.2.
All carbon bound H-atoms were placed at calculated positions and were refined on their parent atoms with their Uiso set to 1.2Ueq. Nitrogen bound H-atoms were located in a difference Fourier map and refined isotropically with their Uiso set to 1.2Ueq of the carrier N-atom.
Reviewer 2 Report
Overall this is a good paper, well written and presenting a thorough study of the X-ray structure of dicyclohexylammonium diphenylphosphate as well as its spectra using each of the main techniques. It is rather remarkable that the structure of this simple salt has not been studied before (the only previous reference is a brief mention in J Org Chem 1964 with mp only) so the current paper makes a welcome addition to the literature. There are only a few minor errors to be corrected.
Abstract, line 6 - change 'detail' to 'detailed'
Table 1 relates directly to Figure 1 and should appear earlier in the final version so that the two can be read at the same time.
The same applies for Table 2 and Figure 2.
Figure 3, caption - change 'for the clarity purpose' to 'for the sake of clarity'
Figure 7 A - the label of atom O4 is missing
Figure 9 - The Hirshfield surfaces appear as described in the caption, but the function of the ball and stick models, which appear in the opposite order, is unclear. Perhaps this is intentional, but I think the ball and stick models have simply been swapped between top and bottom and should correspond to the Hirshfield surfaces beside them.
The supplementary material is of a good quality and does not need any changes.
Author Response
Dear Reviewer,
First of all, thank you very much for reviewing our paper and the time which you spent on. We corrected the paper according to the useful commnets. Details of corrections are as follows:
Overall this is a good paper, well written and presenting a thorough study of the X-ray structure of dicyclohexylammonium diphenylphosphate as well as its spectra using each of the main techniques. It is rather remarkable that the structure of this simple salt has not been studied before (the only previous reference is a brief mention in J Org Chem 1964 with mp only) so the current paper makes a welcome addition to the literature. There are only a few minor errors to be corrected.
Point 1 : Abstract, line 6 - change 'detail' to 'detailed'
Response : Corrected as suggested.
Point 2 : Table 1 relates directly to Figure 1 and should appear earlier in the final version so that the two can be read at the same time.
Response : Table 1 is moved immediately after Figure 1.
Point 3 : The same applies for Table 2 and Figure 2.
Response : Table 2, and figure 2 are moved as suggested.
Point 4 : Figure 3, caption - change 'for the clarity purpose' to 'for the sake of clarity'
Response : Text is corrected as suggested.
Point 5 : Figure 7 A - the label of atom O4 is missing
Response : The atom label O4 is included.
Point 6 : Figure 9 - The Hirshfield surfaces appear as described in the caption, but the function of the ball and stick models, which appear in the opposite order, is unclear. Perhaps this is intentional, but I think the ball and stick models have simply been swapped between top and bottom and should correspond to the Hirshfield surfaces beside them.
Response : The Hirshfeld surface map was re-drawn and the related text was corrected.
Point 7: The supplementary material is of a good quality and does not need any changes.
Response: Thank you.
