(Last updated February 2026)
Figure . The molecular diagrams of cannabinol and tetramethylpyrazine.
This was a stoichiometry study in the Blind Test. Two stoichiometries exist, with fewer than four molecules in the asymmetric unit.
| REFCODE | CANNOL |
|---|---|
| Formula | C21 O2 H26 |
| Common Name | Cannabinol |
| IUPAC Systematic Name | 6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol |
| Other Names | |
| CSD Refcodes | CANNOL01 |
| Search Identifier | A |
| Scientist | Yiming Ding |
| Date | January 2021 |
| Publication | Blind Test 7 (one component of XXX cocrystals) |
| Energy model | 1 |
| Study_ID | 10 |
| Programs | CrystalPredictor (2.4.3.2), CrystalOptimizer (2.4.7.1), DMACRYS (2.3.1.1) |
| Location on S Drive | CHEMISTRY_CPOSS\\BlindTest2020-2022\\XXX\\CANNOL |
| Potential Description | CrystalPredictor2.4.3.2(torsion groups) + CrystalOptimizer with GDMA2.2(PBE1PBE/6-31G(d,p)) + FIT |
| Intramolecular Description | PBE0/6-31G(d,p) |
| REFCODE | MPYRAZ |
| Formula | C8 N2 H12 |
| Common Name | Tetramethylpyrazine |
| IUPAC Systematic Name | Tetramethylpyrazine |
| Other Names | |
| CSD Refcodes | MPYRAZ02 |
| Search Identifier | A |
| Scientist | Yiming Ding |
| Date | January 2021 |
| Publication | Blind Test 7 (one component of XXX cocrystals) |
| Energy model | 1 |
| Study_ID | 20 |
| Programs | CrystalPredictor (2.4.3), CrystalOptimizer (2.4.7.1), DMACRYS (2.3.1.1) |
| Location on S Drive | CHEMISTRY_CPOSS\\BlindTest2020-2022\\XXX\\MPYRAZ\\ |
| Potential Description | Rigid CrystalPredictor + DMACRYS with GDMA2.2(PBE1PBE/6-31G(d,p)) + FIT |
| Intramolecular Description | PBE1PBE/6-31G(d,p) |
| Energy model | 2 |
| Study_ID | 10 |
| Programs | CrystalPredictor (2.4.3), CrystalOptimizer (2.4.7.1), DMACRYS (2.3.1.1) |
| Location on S Drive | CHEMISTRY_CPOSS\\BlindTest2020-2022\\XXX\\MPYRAZ\\ |
| Potential Description | CrystalOptimizer with GDMA2.2(PBE0/6-31G(d,p)) + FIT |
| Intramolecular Description | PBE1PBE/6-31G(d,p) |
| REFCODE | MIVZIE |
| Formula | C21 O2 H26 - C8 N2 H12 |
| Common Name | Blind Test XXX, stoichiometry test; Cannabinol Tetramethylpyrazine 1-1 cocrystal |
| IUPAC Systematic Name | 6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol - Tetramethylpyrazine cocrystal |
| Other Names | |
| CSD Refcodes | MIVZIE |
| Search Identifier | A |
| Scientist | Yiming Ding |
| Date | June 2021 |
| Publication | Hunnisett LM, et al, Acta Cryst B, 2024, 80(6), 517-547 DOI: Open paper (10.1107/S2052520624007492) |
| Energy model | 1 |
| Study_ID | 10 |
| Programs | CrystalPredictor (2.4.3.2) CrystalOptimize (2.4.7.1) |
| Location on S Drive | \\CHEMISTRY_CPOSS\\BlindTest2020-2022\\BXXXCT |
| Potential Description | CrystalPredictor2.4.3.2(torsion groups) + CrystalOptimizer with GDMA2.2(PBE0/6-31G(d,p)) + FIT |
| Intramolecular Description | PBE0/6-31G(d,p) |
| REFCODE | MIVZEA |
| Formula | 2 [ C21 O2 H26 ] - C8 N2 H12 |
| Common Name | Blind Test XXX, stoichiometry test; Cannabinol Tetramethylpyrazine 2-1 cocrystal |
| IUPAC Systematic Name | 6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol - Tetramethylpyrazine 2-1 cocrystal |
| Other Names | |
| CSD Refcodes | MIVZEA |
| Search Identifier | A |
| Scientist | Yiming Ding |
| Date | June 2021 |
| Publication | Hunnisett LM, et al, Acta Cryst B, 2024, 80(6), 517-547 DOI: Open paper (10.1107/S2052520624007492) |
| Energy model | 1 |
| Study_ID | 10 |
| Programs | CrystalPredictor (2.4.3.2) CrystalOptimize (2.4.7.1) |
| Location on S Drive | \\CHEMISTRY_CPOSS\\BlindTest2020-2022\\XXXCCT |
| Potential Description | CrystalPredictor2.4.3.2(torsion groups) + CrystalOptimizer with GDMA2.2(PBE0/6-31G(d,p)) + FIT |
| Intramolecular Description | PBE0/6-31G(d,p) |
| REFCODE | XXXCTT |
| Formula | C21 O2 H26 - 2 [ C8 N2 H12 ] |
| Common Name | Blind Test XXX, stoichiometry test; Cannabinol Tetramethylpyrazine 1-2 cocrystal |
| IUPAC Systematic Name | 6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol - Tetramethylpyrazine 1-2 cocrystal |
| Other Names | |
| CSD Refcodes | |
| Search Identifier | A |
| Scientist | Yiming Ding |
| Date | June 2021 |
| Publication | Hunnisett LM, et al, Acta Cryst B, 2024, 80(6), 517-547 DOI: Open paper (10.1107/S2052520624007492) |
| Energy model | 1 |
| Study_ID | 10 |
| Programs | CrystalPredictor (2.4.3.2) CrystalOptimizer (2.4.7.1) |
| Location on S Drive | \\CHEMISTRY_CPOSS\\BlindTest2020-2022\\XXXCTT |
| Potential Description | CrystalPredictor2.4.3.2(torsion groups) + CrystalOptimizer with GDMA2.2(PBE0/6-31G(d,p)) + FIT |
| Intramolecular Description | PBE0/6-31G(d,p) |
\n
Figure . Crystal energy landscape of cannabinol tetramethylpyrazine cocrystal from previous work. Top row: Cannabinol_A1, Tetramethylpyrazine_A1, . Bottom row: CannabinolTetramethylpyrazine_A1, 2CannabinolTetramethylpyrazine_A1.
Table . Crystallographic information for CSD entries for cannabinol tetramethylpyrazine cocrystal. Different polymorphs are coloured differently.
| REFCODE | space group | Z’ | a / Å | b / Å | c / Å | α / ° | β / ° | γ / ° | density / g cm-3 | Form |
|---|---|---|---|---|---|---|---|---|---|---|
| CANNOL | P21/c | 2.0 | 20.658 | 18.166 | 13.517 | 90.0 | 133.56 | 90.0 | 1.1218 | None |
| CANNOL01 | P21/c | 2.0 | 14.7920 | 17.8307 | 13.4231 | 90.0 | 91.849 | 90.0 | 1.1654 | None |
| MPYRAZ | Pbca | 0.5 | 8.35 | 9.27 | 10.6200 | 90.0 | 90.0 | 90.0 | 1.1004 | orthorhombic polymorph |
| MPYRAZ01 | Pbca | 0.5 | 8.328 | 9.27 | 10.2000 | 90.0 | 90.0 | 90.0 | 1.1488 | orthorhombic polymorph |
| MPYRAZ02 | Pbca | 0.5 | 8.331 | 9.225 | 10.148 | 90.0 | 90.0 | 90.0 | 1.1599 | orthorhombic polymorph |
| MIVZIE | P21/n | 1.0 | 14.8774 | 10.119 | 17.5619 | 90.0 | 104.42800 | 90.0 | 1.1585 | None |
| MIVZIE01 | P21/n | 1.0 | 14.8774 | 10.119 | 17.5619 | 90.0 | 104.42800 | 90.0 | 0.0 | None |
| MIVZEA | P21/c | 1.0 | 24.3576 | 8.7626 | 22.1068 | 90.0 | 114.51870 | 90.0 | 1.1713 | None |
| MIVZEA01 | P21/c | 1.0 | 24.3576 | 8.7626 | 22.1068 | 90.0 | 114.51870 | 90.0 | 0.0 | None |
Table . Experimental information for CSD entries for cannabinol tetramethylpyrazine cocrystal.
| REFCODE | space group | R factor | T / K | Year | Comments |
|---|---|---|---|---|---|
| CANNOL | P21/c | 9.1 | None | 1977 | 10.3891/acta.chem.scand.31b-0781 |
| CANNOL01 | P21/c | 5.64 | 173 K | 2022 | Private communication |
| MPYRAZ | Pbca | 23.0 | None | 1951 | 10.1021/ja01156a025 |
| MPYRAZ01 | Pbca | 8.4 | None | 1981 | 10.1107/S056774088100410X |
| MPYRAZ02 | Pbca | 4.5 | at 100 K | 1981 | 10.1107/S056774088100410X |
| MIVZIE | P21/n | 4.100 | 100 K | 2023 | Private communication |
| MIVZIE01 | P21/n | 4.100 | 100 K | 2024 | 10.1107/S2052520624007492 |
| MIVZEA | P21/c | 3.719 | 100 K | 2023 | Private communication |
| MIVZEA01 | P21/c | 3.719 | 100 K | 2024 | 10.1107/S2052520624007492 |
Make this table include whether polymorphs are solution-grown, sublimation grown, templated or otherwise. Add references.