(Last updated December 2025)
Figure . The molecular diagrams of the 2-halobenzamides.
| REFCODE | BIGSUF |
|---|---|
| Formula | C7 H6 N1 O1 F1 |
| Common Name | 2-Fluorobenzamide |
| IUPAC Systematic Name | 2-Fluorobenzamide |
| Other Names | 2-Fluorobenzamide |
| CSD Refcodes | BIGSUF01 |
| Search Identifier | A |
| Scientist | Anastasia Ntantou |
| Date | pre-2010 |
| Publication | Masters thesis |
| Energy model | 1 |
| Study_ID | 0 |
| Programs | MOLPAK, DMAREL (4.1.1) |
| Location on S Drive | CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\2-fluorobenzamide\\opt |
| Potential Description | DMA + FIT |
| Intramolecular Description | MP2/6-31G(d,p) |
| Search Identifier | B |
| Scientist | Anastasia Ntantou |
| Date | pre-2010 |
| Publication | Masters thesis |
| Energy model | 1 |
| Study_ID | 1 |
| Programs | MOLPAK, DMAREL (4.1.1) |
| Location on S Drive | CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\2-fluorobenzamide\\con_opt |
| Potential Description | DMA + FIT |
| Intramolecular Description | MP2/6-31G(d,p) |
| REFCODE | CLBZAM |
| Formula | C7 H6 N1 O1 Cl1 |
| Common Name | 2-Chlorobenzamide |
| IUPAC Systematic Name | 2-Chlorobenzamide |
| Other Names | 2-Chlorobenzamide |
| CSD Refcodes | CLBZAM12, CLBZAM11, CLBZAM13 |
| Search Identifier | A |
| Scientist | Louise Price |
| Date | 2011 |
| Publication | Cockcroft JK; Buanz ABM; Ntantou A; Price LS; Tocher DA; Vickers M; Lancaster RW, Crystal Growth & Design 2016, 16(11), 6144-6147 DOI: Open paper (10.1021/acs.cgd.6b00973) |
| Energy model | 1 |
| Study_ID | 10 |
| Programs | Flexible CrystalPredictor (1.x), CrystalOptimizer (x), DMACRYS (2.0.4) |
| Location on S Drive | \\CHEMISTRY_CPOSS\\2-chlorobenzamide_CPCO |
| Potential Description | CrystalOptimizer, GDMA2.2 (MP2/6-31G(d,p)) multipoles, MP2/6-31G(d,p) intra, FIT |
| Intramolecular Description | MP2/6-31G(d,p) |
| Search Identifier | B |
| Scientist | Anastasia Ntantou |
| Date | pre-2010 |
| Publication | Masters thesis only |
| Energy model | 1 |
| Study_ID | 0 |
| Programs | MOLPAK, DMAREL (4.1.1) |
| Location on S Drive | \\CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\2-chlorobenzamide |
| Potential Description | DMA + FIT + CL (DAY & PRICE 2003) |
| Intramolecular Description | MP2/6-31G(d,p) |
| Search Identifier | C |
| Scientist | Bob Lancaster |
| Date | pre-2010 |
| Publication | No publication planned |
| Energy model | 1 |
| Study_ID | 2 |
| Programs | MOLPAK, DMACRYS (1.1.1) |
| Location on S Drive | \\CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\2-chlorobenzamide_BOB |
| Potential Description | DMA + FIT |
| Intramolecular Description | MP2/6-31G(d,p) |
| REFCODE | BRBZAO |
| Formula | C7 H6 N1 O1 Br1 |
| Common Name | o-bromobenzamide |
| IUPAC Systematic Name | 2-bromobenzamide |
| Other Names | 2-bromobenzamide |
| CSD Refcodes | BRBZAO01 |
| Search Identifier | A |
| Scientist | Anastasia Ntantou |
| Date | pre-2010 |
| Publication | Masters thesis |
| Energy model | 1 |
| Study_ID | 0 |
| Programs | MOLPAK, DMAREL (4.1.1) |
| Location on S Drive | \\CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\2-bromobenzamide |
| Potential Description | DMA + FIT + isotropic BR from blind test |
| Intramolecular Description | MP2/6-31G(d,p) |
Figure . Crystal energy landscape of the 2-halobenzamides from previous work. 1st box: Fluorobenzamide. Left: from Study_ID=1. Right: from Study_ID=1. 2nd box: Chlorobenzamide. Top: from Study_ID=10. Bottom left: from Study_ID=0. Bottom right: from Study_ID=2. 3rd box: Bromobenzamide, Study_ID=0.
Table . Crystallographic information for CSD entries for 2-halobenzamides. Different polymorphs are coloured differently.
| REFCODE | space group | Z’ | a / Å | b / Å | c / Å | α / ° | β / ° | γ / ° | density / g cm-3 | Form |
|---|---|---|---|---|---|---|---|---|---|---|
| BIGSUF | P21/a | 2.0 | 12.695 | 20.534 | 5.133 | 90.0 | 97.8 | 90.0 | 1.3941 | None |
| BIGSUF01 | P21/c | 2 | 5.126(<1) | 20.368(1) | 12.322(1) | 90 | 96.69(<1) | 90 | 1.447 | None |
| CLBZAM10 | P21/n | 1.0 | 14.127 | 10.683 | 5.051 | 90.0 | 90.2 | 90.0 | 1.3556 | alpha form |
| CLBZAM11 | P212121 | 1.0 | 14.0300 | 10.599 | 5.064 | 90.0 | 90.0 | 90.0 | 1.3723 | beta form |
| CLBZAM12 | P21/n | 1.0 | 5.05934 | 10.3235 | 14.2631 | 90.0 | 92.187 | 90.0 | 1.3881 | alpha form |
| CLBZAM13 | P212121 | 1.0 | 5.06073 | 10.3791 | 13.9351 | 90.0 | 90.0 | 90.0 | 1.4118 | beta form |
| BRBZAO | P21/a | 1.0 | 13.92 | 11.43 | 5.02000 | 90.0 | 107.0 | 90.0 | 1.7394 | None |
| BRBZAO01 | P21/n | 1.0 | 5.0263 | 10.9683 | 13.3113 | 90.0 | 93.465 | 90.0 | 1.8138 | None |
| BRBZAO02 | P21/n | 1.o | 5.024(<1) | 11.402(1) | 13.313(1) | 90 | 93.76(<1) | 90 | 1.746 | None |
CLBZAM11 and CLBZAM13 are notionally the same form. However Louise can’t overlay them in Mercury and they have different structure matches. The are possibly enantiomers (needs more investigation, which I don’t have time for!).
Two other polymorphs of 2-chlorobenzamide are reported, CLBZAM02 gamma and CLBZMA03 delta. Neither have space groups or full structures.
Table . Experimental information for CSD entries for XXX.
| REFCODE | space group | R factor | T / K | Year | Comments |
|---|---|---|---|---|---|
| BIGSUF | P21/a | 7.60 | None | 1982 | 10.1246/bcsj.55.1643 |
| BIGSUF01 | P21/c | 4.39 | 100 | 2024 | 10.1021/acs.cgd.4c00517 |
| CLBZAM10 | P21/n | 9.700 | None | 1974 | 10.1107/S0567740874007801 |
| CLBZAM11 | P212121 | 6.5 | None | 1974 | 10.1107/S0567740874007801 |
| CLBZAM12 | P21/n | 3.0 | 150 K | 2016 | 10.1021/acs.cgd.6b00973 |
| CLBZAM13 | P212121 | 2.2 | 150 K | 2016 | 10.1021/acs.cgd.6b00973 |
| BRBZAO | P21/a | 16.0 | None | 1972 | None |
| BRBZAO01 | P21/n | 1.97 | 100 K | 2015 | 10.1039/C5CY00627A |
| BRBZAO02 | p21/N | 2.69 | 296 k | 2021 | 10.1021/acs.cgd.0c01119 |
Make this table include whether polymorphs are solution-grown, sublimation grown, templated or otherwise. Add references.
There was no .pot file for CLBZAM Study_ID = 10. The pote.dat files were compared for Bob’s search and Louise’s search, and differed only in the H_F2 ClF1 cross term.
| Bob’s search | |||||||||
|---|---|---|---|---|---|---|---|---|---|
| BUCK | H_F2 | H_F2 | 52.12899 | 0.214592 | 0.222819 | 0 | 70 | ||
| BUCK | ClF1 | ClF1 | 9583.58 | 0.2849 | 80.22445 | 0 | 70 | ||
| BUCK | ClF1 | H_F2 | 446.9519 | 0.214592 | 2.373693 | 0 | 70 | ||
| Louise’s search | |||||||||
| BUCK | H_F2 | H_F2 | 52.12899 | 0.214592 | 0.222819 | 0 | 70 | ||
| BUCK | ClF1 | ClF1 | 9583.58 | 0.2849 | 80.22445 | 0 | 70 | ||
| BUCK | ClF1 | H_F2 | 706.8114 | 0.244798 | 4.227947 | 0 | 70 | ||
| Anastasia’s search | |||||||||
| BUCK | HP | CODA | HP | CODA | 52.12899 | 0.214592 | 0.222819 | 0 | 70 |
| BUCK | CL | CODA | CL | CODA | 5905.001 | 0.299159 | 86.7168 | 0 | 70 |
| BUCK | CL | CODA | HP | CODA | 554.8123 | 0.256857 | 4.395825 | 0 | 70 |
| Cross potential from crosspot | |||||||||
| BUCK | H_F2 | ClF1 | 706.8114 | 0.244798 | 4.227947 | 0 | 70 | ||
| Anastasia’s cross potential from crosspot | |||||||||
| BUCK | H_F2 | ClF1 | 554.8168 | 0.249915 | 4.395697 | 0 | 70 |
The chlorine potential was different in the case of Anastasia’s search. The cross term was consistent (within rounding errors in Excel). The cross potential used by Bob’s search was wrong.
No ZIP datasets are currently available for this case.