5-substituted uracils

(Last updated January 2026)

This is all the molecules covered in Sarah Barnett’s paper, Barnett SA, Hulme AT, Issa N, Lewis TC, Price LS, Tocher DA, Price SL 2008. New J Chem 32, 1761-1775.:1761-1775. 5-fluorouracil is also covered in a separate file. 5-eniluracil’s search was not covered in that paper as it was covered in Copley RCB, Barnett SA, Karamertzanis PG, Harris KDM, Kariuki BM, Xu MC, Nickels EA, Lancaster RW, Price SL 2008. Cryst Growth Des 8

Embedded image

Figure 1. The molecular diagram of 5-aminouracil, 5-chlorouracil, 5-cyanouracil, 5-ethyluracil, 5-ethynyluracil (eniluracil), 5-fluorouracil, 5-hydroxyuracil (isobarbituric acid), 5-iodouracil, 5-methyluracil (thymine), 5-nitrouracil, 5-vinyluracil, uracil.

CSP studies

REFCODE	UCLAUR
Formula	C4 H5 N3 O2
Common Name	5-aminouracil
IUPAC Systematic Name	5-aminouracil
Other Names	5-aminouracil
CSD Refcodes

Search Identifier	A
Scientist	Nizar Issa (Louise Price)
Date	2008
Publication	Barnett SA, Hulme AT, Issa N, Lewis TC, Price LS, Tocher DA, Price SL 2008. New J Chem 32, 1761-1775.,1761-1775. DOI: Open paper (10.1039/b806763e)
Energy model	1
Study_ID	0
Programs	MOLPAK, DMAREL (4.1.1)
Location on S Drive	\\CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\5-aminouracil
Potential Description	DMA + FIT
Intramolecular Description	MP2/6-31G(d,p)

REFCODE	CLURAC
Formula	C4 H3 N2 O2 Cl
Common Name	5-chlorouracil
IUPAC Systematic Name	5-chloropyrimidine-2,4(1H,3H)-dione
Other Names	5-chlorouracil
CSD Refcodes	CLURAC11

Search Identifier	A
Scientist	Ashley Hulme
Date	2005-7
Publication	Barnett SA, Hulme AT, Issa N, Lewis TC, Price LS, Tocher DA, Price SL 2008. New J Chem 32, 1761-1775. DOI: Open paper (10.1039/b806763e)
Energy model	1
Study_ID	0
Programs	MOLPAK, DMAREL (4.1.1)
Location on S Drive	\\CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\chlorouracil
Potential Description	DMA + FIT with anisotropic chlorine potential
Intramolecular Description	MP2/6-31G(d,p)

REFCODE	BOLLOE
Formula	C5 H3 N3 O2
Common Name	5-cyanouracil
IUPAC Systematic Name	5-cyanouracil
Other Names	5-cyanouracil
CSD Refcodes	BOLLOE

Search Identifier	A
Scientist	Nizar Issa
Date	2005-7
Publication	Barnett SA, Hulme AT, Issa N, Lewis TC, Price LS, Tocher DA, Price SL 2008. New J Chem 32, 1761-1775. DOI: Open paper (10.1039/b806763e)
Energy model	1
Study_ID	0
Programs	MOLPAK, DMAREL (4.1.1)
Location on S Drive	\\CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\5-cyanouracil
Potential Description	DMA + FIT
Intramolecular Description	MP2/6-31G(d,p)

REFCODE	BOLLIY
Formula	C6 H8 N2 O2
Common Name	5-Ethyluracil
IUPAC Systematic Name	5-Ethyluracil
Other Names	5-Ethyluracil
CSD Refcodes

Search Identifier	A
Scientist	Nizar Issa (Weijia Zhu)
Date	2005-7
Publication	Barnett SA, Hulme AT, Issa N, Lewis TC, Price LS, Tocher DA, Price SL 2008. New J Chem 32, 1761-1775.-1761-1775. DOI: Open paper (10.1039/b806763e)
Energy model	1
Study_ID	0
Programs	MOLPAK, DMAREL (4.1.1)
Location on S Drive	\\CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\5-ethyluracil
Potential Description	DMA + FIT
Intramolecular Description	MP2/6-31G(d,p)

REFCODE	DOHFEM
Formula	C6 H4 N2 O2
Common Name	Eniluracil
IUPAC Systematic Name	5-ethynylpyrimidine-2,4(1H,3H)-dione
Other Names	5-ethynyluracil
CSD Refcodes	DOHFEM01

Search Identifier	A
Scientist	Sarah Barnett
Date	2005-7
Publication	Copley RCB, Barnett SA, Karamertzanis PG, Harris KDM, Kariuki BM, Xu MC, Nickels EA, Lancaster RW, Price SL 2008. Cryst Growth Des 8 DOI: Open paper (10.1021/cg800517h)
Energy model	1
Study_ID	0
Programs	MOLPAK, DMAREL (4.1.1)
Location on S Drive	\\CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\eniluracil
Potential Description	DMA + FIT
Intramolecular Description	MP2/6-31G(d,p)

Search Identifier	B
Scientist	Louise Price
Date	2007
Publication	Barnett SA, Hulme AT, Issa N, Lewis TC, Price LS, Tocher DA, Price SL 2008. New J Chem 32, 1761-1775. DOI: Open paper (10.1039/b806763e)
Energy model	1
Study_ID	1
Programs	MOLPAK, DMAREL (4.1.1)
Location on S Drive	\\CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\eniluracil_revisited
Potential Description	DMA + FIT
Intramolecular Description	MP2/6-31G(d,p)

REFCODE	QARWAI
Formula	C4 H4 N2 03
Common Name	Isobarbituric acid
IUPAC Systematic Name	5-hydroxy-1H-pyrimidine-2,4-dione
Other Names	5-hydroxyuracil
CSD Refcodes	QARWAI

Search Identifier	A
Scientist	Tom Lewis
Date	2005
Publication	Copley, R. C. B., Deprez, L. S., Lewis, T. C., Price, S. L., CrystEngComm, 7(69), 421-428 (2005) DOI: Open paper (10.1039/b504756k)
Energy model	1
Study_ID	0
Programs	MOLPAK, DMAREL (3.0)
Location on S Drive	\\CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\isobarbituric_acid
Potential Description	MP2 6-31G(d,p) DMA + 25% reduced Carbon repulsion FIT
Intramolecular Description	B3LYP/6-31G(d,p)

Search Identifier	B
Scientist	Louise Price
Date	2005-7
Publication	Barnett SA, Hulme AT, Issa N, Lewis TC, Price LS, Tocher DA, Price SL 2008. New J Chem 32, 1761-1775. DOI: Open paper (10.1039/b806763e)
Energy model	1
Study_ID	1
Programs	MOLPAK, DMAREL (4.1.1)
Location on S Drive	\\CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\isobarbituric_acid_revisited
Potential Description	DMA + FIT
Intramolecular Description	MP2/6-31G(d,p)

REFCODE	THYMIN
Formula	C5 H6 N2 O2
Common Name	Thymine
IUPAC Systematic Name	5-methyl-2,4(1H,3H)-pyrimidinedione
Other Names	2,4-dihydroxy-5-methylpyrimidine, 5-methyluracil
CSD Refcodes	THYMIN01, THYMIN03

Search Identifier	A
Scientist	Tom Lewis
Date	2005
Publication	See Study_ID=1
Energy model	1
Study_ID	0
Programs	MOLPAK, DMAREL (4.1.1)
Location on S Drive	\\CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\thymine
Potential Description	MP2 6-31G(d,p) DMA + 25% reduced Carbon repulsion FIT
Intramolecular Description	MP2/6-31G(d,p)

Search Identifier	B
Scientist	Louise Price
Date	2005-7
Publication	Barnett SA, Hulme AT, Issa N, Lewis TC, Price LS, Tocher DA, Price SL 2008. New J Chem 32, 1761-1775. DOI: Open paper (10.1039/b806763e)
Energy model	1
Study_ID	1
Programs	MOLPAK, DMAREL (4.1.1)
Location on S Drive	\\CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\thymine_revisited
Potential Description	DMA + FIT
Intramolecular Description	MP2/6-31G(d,p)

REFCODE	NIMFOE
Formula	C4 H3 N3 O4
Common Name	5-nitrouracil
IUPAC Systematic Name	5-nitro-1H-pyrimidine-2,4-dione
Other Names
CSD Refcodes	NIMFOE, NIMFOE01, NIMFOE02, many solvates

Search Identifier	A
Scientist	Nizar Issa
Date	2005-7
Publication	Barnett SA, Hulme AT, Issa N, Lewis TC, Price LS, Tocher DA, Price SL 2008. New J Chem 32, 1761-1775. DOI: Open paper (10.1039/b806763e)
Energy model	1
Study_ID	0
Programs	MOLPAK, DMAREL (4.1.1)
Location on S Drive	\\CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\5-nitrouracil\\OptSearch
Potential Description	DMA + FIT
Intramolecular Description	MP2/6-31G(d,p)

Search Identifier	B
Scientist	Nizar Issa
Date	2005-7
Publication	Barnett SA, Hulme AT, Issa N, Lewis TC, Price LS, Tocher DA, Price SL 2008. New J Chem 32, 1761-1775. DOI: Open paper (10.1039/b806763e)
Energy model	1
Study_ID	1
Programs	MOLPAK, DMAREL (4.1.1)
Location on S Drive	\\CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\5-nitrouracil\\PlanSearch
Potential Description	DMA + FIT
Intramolecular Description	MP2/6-31G(d,p)

REFCODE	UCLVUR
Formula	C6 H6 N2 O2
Common Name	5-vinyluracil
IUPAC Systematic Name	5-vinyl-1H-pyrimidine-2,4-dione
Other Names
CSD Refcodes

Search Identifier	A
Scientist	Tom Lewis
Date	2005-7
Publication	Barnett SA, Hulme AT, Issa N, Lewis TC, Price LS, Tocher DA, Price SL 2008. New J Chem 32, 1761-1775. DOI: Open paper (10.1039/b806763e)
Energy model	1
Study_ID	0
Programs	MOLPAK, DMAREL (4.1.1)
Location on S Drive	\\CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\5-vinyluracil
Potential Description	DMA + FIT
Intramolecular Description	MP2/6-31G(d,p)

REFCODE	URACIL
Formula	C4 H4 N2 O2
Common Name	Uracil
IUPAC Systematic Name	2,4-pyrimidine dione
Other Names
CSD Refcodes	URACIL

Search Identifier	A
Scientist	Tom Lewis
Date	2005-7
Publication	Barnett SA, Hulme AT, Issa N, Lewis TC, Price LS, Tocher DA, Price SL 2008. New J Chem 32, 1761-1775. DOI: Open paper (10.1039/b806763e)
Energy model	1
Study_ID	0
Programs	MOLPAK, DMAREL (4.1.1)
Location on S Drive	\\CHEMISTRY_CPOSS\\0-EarlySearches\\home\\louise_price.eminerals\\uracil
Potential Description	DMA + FIT
Intramolecular Description	MP2/6-31G(d,p)

Embedded image

Figure 2. Crystal energy landscape of 5-substituted uracils from previous work. From top left to bottom right, 5-aminouracil, 5-chlorouracil, 5-cyanouracil, 5-ethyluracil, 5-ethynyluracil_B1 (eniluracil), 5-hydroxyuracil_B1 (isobarbituric acid), 5-methyluracil_B1 (thymine), 5-nitrouracil_A1 and _B1, 5-vinyluracil, uracil.

CSD structures (CSD version 6.01)

Table 1. Crystallographic information for CSD entries for 5-substituted uracils. Different polymorphs are coloured differently.

REFCODE	space group	Z’	a / Å	b / Å	c / Å	α / °	β / °	γ / °	density / g cm^-3	Form
CLURAC10	P21/c	1.0	8.45	6.84200	11.0720	90.0	123.53	90.0	1.6122	P21/c polymorph
CLURAC11	P21/n	1.0	8.43930	6.84120	9.3679	90.0	104.20100	90.0	1.8562	P21/n polymorph
CLURAC12	P21/m	0.5	5.532	6.841	7.152	90.0	97.31	90.0	1.8002	P21/m polymorph
CLURAC14	P21/m	0.5	5.51500	6.8639	7.126	90.0	96.92	90.0	1.8110	P21/m polymorph
BOLLOE	P21/n	1.0	9.0098	6.6035	9.1805	90.0	98.124	90.0	1.6840	None
BOLLIY	P-1	1.0	3.91930	5.75400	14.366	100.027	96.109000	92.374	1.4699	None
DOHFEM	P21/n	1.0	9.0169	6.8086	9.3777	90.0	101.2085	90.0	1.6008	None
DOHFEM01	P21	2.0	9.0188	6.8105	9.3622	90.0	101.18870	90.0	1.6025	None
QARWAI	P-1	1.0	4.6195	7.04930	7.3452	88.169000	81.504	86.245	1.8024	None
THYMIN	P21/c	1.0	12.8700	6.83	6.7	90.0	105.00000	90.0	1.4724	None
THYMIN01	P21/c	1.0	12.8890	6.852	6.784	90.0	104.92	90.0	1.4469	None
THYMIN02	C2/c	1.0	25.107	6.84620	6.715	90.0	90.529	90.0	1.4515	None
THYMIN03	C2/c	1.0	24.919	6.83850	6.6132	90.0	90.081	90.0	1.4866	None
NIMFOE	P21/n	1.0	5.873	9.693	10.4561	90.0	104.07000	90.0	1.8070	monoclinic polymorph
NIMFOE01	Pbca	1.0	8.308	10.426	13.363	90.0	90.0	90.0	1.8028	centrosymmetric orthorhombic polymorph
NIMFOE02	P212121	1.0	5.43420	9.8406	10.3659	90.0	90.0	90.0	1.8822	noncentrosymmetric orthorhombic polymorph
URACIL	P21/a	1.0	11.938	12.3760	3.65520	90.0	120.9	90.0	1.6066	None

Table 2. Experimental information for CSD entries for 5-substituted uracils.

REFCODE	space group	R factor	T / K	Year	Comments
CLURAC10	P21/c	5.8	None	1975	10.1016/0005-2787(75)90130-6
CLURAC11	P21/n	3.300	at 150 K	2008	10.1039/b806763e
CLURAC12	P21/m	4.100	296 K	2014	None
CLURAC14	P21/m	3.500	298 K	2019	10.3390/cryst9090467
BOLLOE	P21/n	3.98	at 150 K	2008	10.1039/b806763e
BOLLIY	P-1	6.09	at 150 K	2008	10.1039/b806763e
DOHFEM	P21/n	4.55	at 150 K	2008	10.1021/cg800517h
DOHFEM01	P21	3.67	at 150 K	2008	10.1021/cg800517h
QARWAI	P-1	4.09	at 150 K	2005	10.1039/b504756k
THYMIN	P21/c	14.9	None	1969	10.1107/S0567740869003505
THYMIN01	P21/c	4.58	None	1999	10.3891/acta.chem.scand.53-0057
THYMIN02	C2/c	8.82	293 K	2016	10.1016/j.molstruc.2016.05.014
THYMIN03	C2/c	4.24	183 K	2016	10.1021/acs.cgd.6b00459
NIMFOE	P21/n	3.63	None	1998	10.1107/S0108270197016521
NIMFOE01	Pbca	7.810	at 130 K	2000	10.1002/1439-7641(20001103)1:3<127::AID-CPHC127>3.3.CO;2-T
NIMFOE02	P212121	7.59	at 130 K	2000	10.1002/1439-7641(20001103)1:3<127::AID-CPHC127>3.3.CO;2-TVinil
URACIL	P21/a	4.5	None	1967	10.1107/S0365110X67004360

Make this table include whether polymorphs are solution-grown, sublimation grown, templated or otherwise. Add references.

5-substituted uracils

CSP studies

CSD structures (CSD version 6.01)

Other notes

Dataset downloads