FOX7 and Trans-FOX7

(Last updated 16 January 2025)

Embedded image

Figure . The molecular diagram of (left) 1,1-diamino-2,2-dinitroethene and (right) (Z)-1,2-diamino-1,2-dinitroethene.

There are phase transitions at 389 and 446 K.

CSP studies

REFCODE	SEDTUQ
Formula	C2 H4 N4 O4
Common Name	FOX-7
IUPAC Systematic Name	1,1-diamino-2,2-dinitroethene
CSD Refcodes	SEDTUQ30, SEDTUQ26, SEDTUQ25, SEDTUQ33
Scientist	Sally Price
Date	2008
Publication	No publication planned.

Search Identifier	A
Energy Model	1
Study_ID	0
Programs	MOLPAK, DMAREL (4.1.1)
Location on S Drive	\\CHEMISTRY_CPOSS\\FOX7\\ConOpt
Potential Description	GDMA2(MP2 6-31G(d,p)) + FIT
Search Identifier	B
Energy Model	1
Study_ID	1
Programs	MOLPAK, DMACRYS (2.0.1)
Location on S Drive	\\CHEMISTRY_CPOSS\\FOX7\\Opt
Potential Description	GDMA2(MP2 6-31G(d,p)) + FIT

REFCODE	TRFOXS
Formula	C2 H4 N4 O4
Common Name	TransFOX-7
IUPAC Systematic Name	(Z)-1,2-diamino-1,2-dinitroethene
CSD Refcodes	N/A
Scientist	Sally Price
Date	2008
Publication	No publication planned.

Search Identifier	A
Energy Model	1
Study_ID	0
Programs	MOLPAK, DMACRYS (2.0.1)
Location on S Drive	\\CHEMISTRY_CPOSS\\FOX7\\TransSearch
Potential Description	GDMA2(MP2 6-31G(d,p)) + FIT

Embedded image

Figure . Crystal energy landscape of FOX7 with the unconstrained optimized conformation, Trans-FOX7 with the unconstrained optimized conformation and FOX7 with the conformation constrained to have planar NH₂ groups.

CSD structures (CSD version 5.43 with Mar, Jun, Sep and Nov 2022 updates)

Table . Crystallographic information for CSD entries for XXX. Different polymorphs are coloured differently.

REFCODE	space group	Z’	a / Å	b / Å	c / Å	α / °	β / °	γ / °	density / g cm^-3	Form
SEDTUQ	P21/n	1	6.941	6.569	11.315	90	90.55	90	1.907	alpha
SEDTUQ01	P21/n	1	6.9396	6.6374	11.3406	90	90.611	90	1.883	alpha
SEDTUQ02	P21/n	1	6.9209	6.5515	11.2741	90	90.06	90	1.924	alpha
SEDTUQ03	P21/n	1	6.934	6.6228	11.3119	90	90.065	90	1.893	alpha
SEDTUQ04	P21/n	1	6.9414	6.6534	11.3316	90	90.082	90	1.879	alpha
SEDTUQ05	P21/n	1	6.9467	6.6887	11.35	90	90.143	90	1.865	alpha
SEDTUQ06	P212121	1	6.9738	6.635	11.6475	90	90	90	1.825	beta
SEDTUQ07	P212121	1	6.972	6.663	11.666	90	90	90	1.815	beta
SEDTUQ08	P212121	1	6.974	6.675	11.673	90	90	90	1.81	beta
SEDTUQ09	P21/n	1	6.922	6.501	11.262	90	90.485	90	1.941	alpha
SEDTUQ10	P212121	1	6.66	6.985	11.672	90	90	90	1.811	beta
SEDTUQ11	P21/n	1	6.922	6.501	11.262	90	90.485	90	1.941	alpha
SEDTUQ12	P21/n	1	6.9295	6.5301	11.275	90	90.53	90	1.928	alpha
SEDTUQ13	P21/n	1	6.7118	6.0361	10.9581	90	90.077	90	2.215	a'
SEDTUQ15	P21/n	1	6.9129	6.4872	11.2465	90	90.4816	90	1.95	alpha
SEDTUQ16	P21/n	1	6.9146	6.4963	11.252	90	90.49	90	1.946	alpha
SEDTUQ17	P21/n	1	6.9165	6.5072	11.2575	90	90.4987	90	1.941	alpha
SEDTUQ18	P21/n	1	6.9184	6.5187	11.2646	90	90.5108	90	1.936	alpha
SEDTUQ19	P21/n	1	6.9209	6.5336	11.2726	90	90.5215	90	1.93	alpha
SEDTUQ20	P21/n	1	6.9254	6.5582	11.2866	90	90.5441	90	1.919	alpha
SEDTUQ21	P21/n	1	6.9303	6.5873	11.3017	90	90.5672	90	1.906	alpha
SEDTUQ22	P21/n	1	6.935	6.619	11.3172	90	90.5886	90	1.893	alpha
SEDTUQ23	P21/n	1	6.9413	6.6532	11.3353	90	90.608	90	1.879	alpha
SEDTUQ24	P21/n	1	6.9484	6.6942	11.3547	90	90.618	90	1.862	alpha
SEDTUQ25	P21/n	2	13.354	6.895	12.05	90	111.102	90	1.9	gamma
SEDTUQ26	P212121	1	6.986	6.686	11.687	90	90	90	1.802	beta
SEDTUQ27	P21/n	1	6.922	6.501	11.262	90	90.485	90	1.941	alpha
SEDTUQ28	P21/n	1	6.922	6.501	11.262	90	90.485	90	1.941	alpha
SEDTUQ29	P21/n	1	6.922	6.501	11.262	90	90.485	90	1.941	alpha
SEDTUQ30	P21/n	1	6.922	6.501	11.262	90	90.485	90	1.941	alpha
SEDTUQ31	P212121	1	6.986	6.671	11.681	90	90	90	1.807	gamma
SEDTUQ32	P212121	1	6.986	6.66	11.674	90	90	90	1.811	beta
SEDTUQ33	P1	2	6.0745	6.6924	6.6972	119.505	93.913	110.042	2.308	polymorph
SEDTUQ34	P1	2	6.0745	6.6924	6.6972	119.505	93.913	110.042	2.308	polymorph
SEDTUQ35	P21/n	1	6.948	6.6364	11.3413	90	90.569	90	1.881
SEDTUQ36	P21/n	1	6.8931	6.5058	11.2567	90	90.48	90	1.948
SEDTUQ37	P21/n	1	6.8358	6.3591	11.163	90	90.314	90	2.027
SEDTUQ38	P21/n	1	6.822	6.3249	11.1378	90	90.263	90	2.047
SEDTUQ39	P21/n	1	6.8011	6.2779	11.1042	90	90.249	90	2.075
SEDTUQ40	P21/n	1	6.7982	6.2473	11.1067	90	90.215	90	2.085
SEDTUQ41	P21/n	1	6.7789	6.7789	11.0632	90	90.2	90	1.935
SEDTUQ42	P21/n	1	6.7562	6.1435	11.0371	90	90.166	90	2.147
SEDTUQ43	P21/n	1	6.7472	6.1083	11.0236	90	90.141	90	2.165
SEDTUQ44	P21/n	1	6.7111	6.0339	10.9621	90	90.086	90	2.216
SEDTUQ45	P1	2	5.9859	6.6716	6.6854	119.463	94.11	110.145	2.358
SEDTUQ46	P1	2	5.8965	6.6394	6.6545	119.395	94.308	110.262	2.421
SEDTUQ47	P1	2	5.8695	6.6197	6.6343	119.409	94.338	110.317	2.449
SEDTUQ48	P1	2	5.7268	6.603	6.6195	119.381	94.429	110.739	2.534
SEDTUQ49	P1	2	5.6947	6.5793	6.5961	119.356	94.461	110.881	2.57

Table . Experimental information for CSD entries for XXX.

REFCODE	space group	R factor	T / K	Year	Comments
SEDTUQ	P21/n	3.12	173	1998	Crystallized from cold N,N-dimethylformamide¹
SEDTUQ01	P21/n	3.02	295	1999	Private communication
SEDTUQ02	P21/n	3.61	200	2006	Slow cooling from DMF or DMSO; Oxford Cryosystems temperature controller on diffractometer²
SEDTUQ03	P21/n	4.02	298	2006	Slow cooling from DMF or DMSO; Oxford Cryosystems temperature controller on diffractometer²
SEDTUQ04	P21/n	4.1	333	2006	Slow cooling from DMF or DMSO; Oxford Cryosystems temperature controller on diffractometer²
SEDTUQ05	P21/n	5.42	373	2006	Slow cooling from DMF or DMSO; Oxford Cryosystems temperature controller on diffractometer²
SEDTUQ06	P212121	3.59	393	2006	Slow cooling from DMF or DMSO; Oxford Cryosystems temperature controller on diffractometer²
SEDTUQ07	P212121	12.3	403	2006	Powder data; finely ground²
SEDTUQ08	P212121	12.4	423	2006	Powder data; finely ground²
SEDTUQ09	P21/n	2.1	100	2008	Synchrotron radiation; recrystallized from 2-propanol³
SEDTUQ10	P212121	4.08	400	2012	Private communication
SEDTUQ11	P21/n	2.14	100	2016	Re-refinement of data collected in SEDTUQ09⁴
SEDTUQ12	P21/n	3.92	153	2018	Crystallized concomitantly with phenanthroline cocrystal⁵
SEDTUQ13	P21/n	11.04	293	2016	Synchrotron; Grown from DMSO solution⁶
SEDTUQ15	P21/n	2.67	80	2022	Synchrotron; Slow evaporation from DMSO⁷
SEDTUQ16	P21/n	2.61	100	2022	Synchrotron; Slow evaporation from DMSO⁷
SEDTUQ17	P21/n	2.79	120	2022	Synchrotron; Slow evaporation from DMSO⁷
SEDTUQ18	P21/n	2.99	140	2022	Synchrotron; Slow evaporation from DMSO⁷
SEDTUQ19	P21/n	3.09	164	2022	Synchrotron; Slow evaporation from DMSO⁷
SEDTUQ20	P21/n	3.34	200	2022	Synchrotron; Slow evaporation from DMSO⁷
SEDTUQ21	P21/n	3.87	240	2022	Synchrotron; Slow evaporation from DMSO⁷
SEDTUQ22	P21/n	5.74	280	2022	Synchrotron; Slow evaporation from DMSO⁷
SEDTUQ23	P21/n	7.74	320	2022	Synchrotron; Slow evaporation from DMSO⁷
SEDTUQ24	P21/n	9.49	360	2022	Synchrotron; Slow evaporation from DMSO⁷
SEDTUQ25	P21/n	6.02	200	2007	Slow heating on diffractometer of crystal prepared for SEDTUQ26⁸ (does not revert to other phases on cooling carefully)
SEDTUQ26	P212121	2.82	423	2007	Slow cooling of DMF or DMSO solutions⁸
SEDTUQ27	P21/n	2.49	100	2020	Re-refinement of data collected in SEDTUQ09⁹
SEDTUQ28	P21/n	2.64	100	2020	Re-refinement of data collected in SEDTUQ09⁹
SEDTUQ29	P21/n	1.95	100	2020	Re-refinement of data collected in SEDTUQ09⁹
SEDTUQ30	P21/n	1.38	100	2020	Re-refinement of data collected in SEDTUQ09⁹
SEDTUQ31	P212121	2.96	413	2007	Intermediate data collections between SEDTUQ26 and SEDTUQ25⁸
SEDTUQ32	P212121	2.89	403	2007	Intermediate data collections between SEDTUQ26 and SEDTUQ25⁸
SEDTUQ33	P1	14.9	293	2016	Synchrotron data, 5.9 GPa⁶ According to a different reference, this is called epsilon
SEDTUQ34	P1	14.9	293	2016	Synchrotron data, 5.9 GPa⁶
SEDTUQ35	P21/n	0	298	2016	Synchrotron data, I don’t understand the publication reference⁶
SEDTUQ36	P21/n	0	298	2016	Synchrotron data, I don’t understand the publication reference⁶
SEDTUQ37	P21/n	0	298	2016	Synchrotron data, I don’t understand the publication reference⁶
SEDTUQ38	P21/n	0	298	2016	Synchrotron data, I don’t understand the publication reference⁶
SEDTUQ39	P21/n	0	298	2016	Synchrotron data, I don’t understand the publication reference⁶
SEDTUQ40	P21/n	0	298	2016	Synchrotron data, I don’t understand the publication reference⁶
SEDTUQ41	P21/n	0	298	2016	Synchrotron data, I don’t understand the publication reference⁶
SEDTUQ42	P21/n	0	298	2016	Synchrotron data, I don’t understand the publication reference⁶
SEDTUQ43	P21/n	0	298	2016	Synchrotron data, I don’t understand the publication reference⁶
SEDTUQ44	P21/n	0	298	2016	Synchrotron data, I don’t understand the publication reference⁶
SEDTUQ45	P1	0	298	2016	Synchrotron data, I don’t understand the publication reference⁶
SEDTUQ46	P1	0	298	2016	Synchrotron data, I don’t understand the publication reference⁶
SEDTUQ47	P1	0	298	2016	Synchrotron data, I don’t understand the publication reference⁶
SEDTUQ48	P1	0	298	2016	Synchrotron data, I don’t understand the publication reference⁶
SEDTUQ49	P1	0	298	2016	Synchrotron data, I don’t understand the publication reference⁶

(1) Bemm, U.; Ostmark, H. 1,1-Diamino-2,2-dinitroethylene: a Novel Energetic Material with Infinite Layers in Two Dimensions. Acta Crystallographica Section C 1998, 54 (12), 1997-1999.

(2) Evers, J.; Klapötke, T. M.; Mayer, P.; Oehlinger, G.; Welch, J. α- and β-FOX-7, Polymorphs of a High Energy Density Material, Studied by X-ray Single Crystal and Powder Investigations in the Temperature Range from 200 to 423 K. Inorganic Chemistry 2006, 45 (13), 4996-5007. DOI: 10.1021/ic052150m.

(3) Meents, A.; Dittrich, B.; Johnas, S. K. J.; Thome, V.; Weckert, E. F. Charge-density studies of energetic materials: CL-20 and FOX-7. Acta Crystallographica Section B 2008, 64 (1), 42-49.

(4) Woińska, M.; Grabowsky, S.; Dominiak, P. M.; Woźniak, K.; Jayatilaka, D. Hydrogen atoms can be located accurately and precisely by x-ray crystallography. Science Advances 2016, 2 (5), e1600192. DOI: doi:10.1126/sciadv.1600192.

(5) Li, K.; Ren, X.; Fu, S.; Zhu, J. Cocrystal structure, thermal behavior, and DFT calculations between FOX–7 and 1,10–Phenanthroline. Journal of Molecular Structure 2018, 1173, 26-32. DOI: https://doi.org/10.1016/j.molstruc.2018.06.090.

(6) Dreger, Z. A.; Stash, A. I.; Yu, Z.-G.; Chen, Y.-S.; Tao, Y.; Gupta, Y. M. High-Pressure Crystal Structures of an Insensitive Energetic Crystal: 1,1-Diamino-2,2-dinitroethene. The Journal of Physical Chemistry C 2016, 120 (2), 1218-1224. DOI: 10.1021/acs.jpcc.5b10644.

(7) Aree, T.; McMonagle, C. J.; Michalchuk, A. A. L.; Chernyshov, D. Low-frequency lattice vibrations from atomic displacement parameters of [alpha]-FOX-7, a high energy density material. Acta Crystallographica Section B 2022, 78 (3 Part 1), 376-384. DOI: doi:10.1107/S2052520622002700.

(8) Crawford, M.-J.; Evers, J.; Göbel, M.; Klapötke, T. M.; Mayer, P.; Oehlinger, G.; Welch, J. M. γ-FOX-7: Structure of a High Energy Density Material Immediately Prior to Decomposition. Propellants, Explosives, Pyrotechnics 2007, 32 (6), 478-495. DOI: https://doi.org/10.1002/prep.200700240 (acccessed 2025/01/16).

(9) Jha, K. K.; Gruza, B.; Kumar, P.; Chodkiewicz, M. L.; Dominiak, P. M. TAAM: a reliable and user friendly tool for hydrogen-atom location using routine X-ray diffraction data. Acta Crystallographica Section B 2020, 76 (3), 296-306. DOI: doi:10.1107/S2052520620002917.

FOX7 and Trans-FOX7

CSP studies

CSD structures (CSD version 5.43 with Mar, Jun, Sep and Nov 2022 updates)

Dataset downloads