# Oxalate chloride

An oxalate chloride or oxalato chloride is a mixed anion compound contains both oxalate and chloride anions.
Related compounds include oxalate fluorides and oxalate bromides.

## Production

Oxalate chlorides may be produced by treating an oxalate salt with concentrated hydrochloric acid, or with a metal oxide dissolved in oxalic acid and hydrochloric acid solutions that are evaporated.

## List

| name | formula | crystal | space group | cell | volume | density | comment |
| Novgorodovaite | Ca$_2$(C$_2$O$_4$)Cl$_2$•2H$_2$O | monoclinic | I2/m | a=6.936 b=7.382 c=7.443 β=94.3° | | | loses water over 205°C; refract: α=1.500 β=1.545 γ=1.568 2V=71° (−) |
| | Ca$_2$(C$_2$O$_4$)Cl$_2$•7H$_2$O | triclinic | P1 | a = 7.3928 b = 8.9925 c = 10.484 α = 84.070 β = 70.95 γ = 88.545° | 655.3 | | looses water at 25°C to 2H$_2$O; refract: α=1.571 β=1.648 γ=1.718 2V=87° (−) |
| | Ca$_4$(C$_2$O$_4$)$_3$Cl$_2$•8H$_2$O | | | | | | dubious |
| octakis(ethyl(dimethyl)ammonium) dodecakis(μ-oxalato)-tetrachloro-tetra-chromium-tetra-manganese | [NH(CH$_3$)$_2$(C$_2$H$_5$)]$_8$[Mn$_4$Cl$_4$Cr$_4$(C$_2$O$_4$)$_{12}$] | monoclinic | P2$_1$ | a=13.8321 b=17.1042 c=20.4209 β=91.874° | | | |
| octakis(diethyl(methyl)ammonium) dodecakis(μ-oxalato)-tetrachloro-tetra-chromium-tetra-manganese | [NH(CH$_3$)(C$_2$H$_5$)$_2$]$_8$[Mn$_4$Cl$_4$Cr$_4$(C$_2$O$_4$)$_{12}$] | monoclinic | P2$_1$ | a=14.1863 b=17.3479 c=20.4140 β=91.937° | | | |
| DABCO=1,4-diazabicyclo[2.2.2]octane; | (DABCO-H$^+$)$_2$(DABCO-2H$^{2+}$)[Mn$^{II}$(CH$_3$OH)(Cl$^−$)Cr$^{III}$(oxalate)$_3$]$^{2−}$$_2$(CH$_3$OH) | triclinic | P1 | a=8.093 b=9.070 c=19.574 α=83.471° β=89.875° γ=86.765° | | | |
| tetrakis(methylammonium) tetrakis(μ-oxalato)-octachloro-tetra-iron(iii) pentahydrate | (MeNH$_3$)$_2$[Fe$_2$(ox)$_2$Cl$_4$]·2.5H$_2$O | monoclinic | P2$_1$/c | a 10.7832 b 13.913 c 13.0578 β 104.060° | | | |
| methylammonium (μ-hydroxo)-bis(μ-oxalato)-dichloro-di-iron(iii) trihydrate | MeNH$_3$[Fe$_2$(OH)(ox)$_2$Cl$_2$]·2H$_2$O | monoclinic | Cc | a=8.945 b=14.936 c=12.408 β=108.531° | | | |
| methylammonium oxonium bis(μ-oxalato)-(μ-oxo)-dichloro-di-iron(iii) dihydrate | (H$_3$O)(MeNH$_3$)[Fe$_2$O(ox)$_2$Cl$_2$]·3H$_2$O | orthorhombic | Fdd2 | a=14.914 b=23.507 c=9.261 | | | |
| DMF = dimethylformamide | Fe$_2$(C$_2$O$_4$)Cl$_4$(DMF)$_4$ | triclinic | P1 | a=8.3919 b=8.7834 c=11.2881 α=70.248° β=71.993° γ=64.423° | | | |
| | (dimim)$_2$[Fe$_2$Cl$_4$(μ-ox)] | | | ionic liquid | | | |
| L$_2$=1,4-bis(imidazol-1-ylmethyl)benzene bis(1,1'-(1,4-Phenylenebis(methylene))bis-1H-imidazol-3-ium) (μ$_2$-oxalato)-tetrachloro-bis(oxalato)-di-iron(iii) | (H$_2$-L$_2$)$_2${Fe$_2$(C$_2$O$_4$)$_3$Cl$_4$} | triclinic | P1 | a=10.6758 b=10.7457 c=10.8774 α=113.219° β=109.138° γ=99.294° Z=1 | 1020.8 | 1.624 | emerald |
| tetramelaminium trioxalatoferrate(III) chloride dihydrate | (C$_3$H$_7$N$_6$)$_4${Fe(C$_2$O$_4$)$_3$}Cl·2H$_2$O | monoclinic | P2$_1$/c | a=11.597 b=22.299 c=13.655 β=94.344° Z=4 | 3521 | 1.698 | green |
| methylammonium (μ-aqua)-tris(μ-chloro)-(μ-oxalato)-iron(iii)-potassium | K(MeNH$_3$)[Fe(ox)Cl$_3$(H$_2$O) | monoclinic | P2$_1$/m | a=8.725 b=7.508 c=9.026 β=112.421° | | | |
| diethylmethylammonium | [NH(CH$_3$)(C$_2$H$_5$)$_2$][FeCl$_2$(C$_2$O$_4$)] | monoclinic | P2$_1$/c | a=8.5125 b=10.775 c=14.9703 β=104.798° Z=4 | 1327.6 | 1.516 | yellow; proton conductor |
| bis(Tetramethylammonium) bis(μ$_2$-oxalato)-tetrachloro-di-iron(iii) | Me$_4$N[Fe$^{III}$(ox)Cl$_2$] | monoclinic | P2$_1$/c | a=7.9441 b=8.6093 c=17.8251 β=91.869 | | | |
| hexakis(Triethylammonium) hexakis(μ$_2$-oxalato)-dodecachloro-hexa-iron(iii) | Et$_3$NH[Fe$^{III}$(ox)Cl$_2$] | triclinic | P1 | a=10.9609 b=14.4602 c=14.5780 α=85.006° β=78.845° γ=83.0191 | | | |
| Triethylammonium (μ$_2$-oxalato)-dichloro-iron(iii) | Et$_3$NH[Fe$^{III}$(ox)Cl$_2$] | orthorhombic | Fdd2 | a=13.5878 b=37.972 c=10.8210 | | | |
| bis(Tetra-n-butylammonium) bis(μ$_2$-oxalato)-tetrachloro-di-iron(iii) | n-Bu$_4$N[Fe$^{III}$(ox)Cl$_2$] | monoclinic | P2$_1$/c | a=8.8836 b=15.1939 c=17.968 β=91.556° | | | |
| | [Fe(oxalato)Cl$_2$]$_3$(3,5-dimethylpyrazole)$_2$(3,5- dimethylpyrazolium)$_2$ | monoclinic | C2/c | a=19.527 b=11.867 c=19.429 β=115.66° Z=4 | 4058.20 | 1.684 | green |
| BETS = Bis(ethylenedithio)tetraselenafulvalene | κ-BETS$_2$[Fe$^{III}$(C$_2$O$_4$)Cl$_2$] | | | | | | black; metallic; |
| bis(2-(5,6-dihydro[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)-5,6-dihydro[1,3]dithiolo[4,5-b][1,4]dithiin-1-ium) bis(μ-oxalato)-tetrachloro-di-iron(iii) | [BEDT-TTF][Fe(C$_2$O$_4$)Cl$_2$] | triclinic | P1 | a=8.896 b=11.401 c=11.427 α=112.062° β=103.775° γ=100.328° | | | |
| BEDT-TTF = Bis(ethylenedithio)tetrathiafulvalene | (BEDT-TTF)[Fe(C$_2$O$_4$)Cl$_2$](CH$_2$Cl$_2$) | monoclinic | P2$_1$/c | a=8.858 b=11.012 c=14.932 β=103.39° | | | |
| tris(ethylenediamine)cobalt(III)chloride oxalate trihydrate | [Co(en)$_3$]Cl(C$_2$O$_4$)·3H$_2$O | monoclinic | C2/c | a = 19.932 b = 9.3344 c = 19.088 β = 96.846° Z = 8 | | | |
| dpyam=di-2-pyridylamine; (μ$_2$-Oxalato)-bis(di-2-pyridylamine)-dichloro-di-copper(ii) | Cu$_2$(dpyam)$_2$(μ-C$_2$O$_4$)(Cl)$_2$ | triclinic | P1 | a=7.4122 b=8.6586 c=9.8002 α=87.900° β=72.022° γ=71.845° | | | |
| L = 3,5-dimethyl-1H-pyrazole | Cu$_2$(C$_2$O$_4$)(L)$_2$Cl$_2$(MeOH)$_2$ | triclinic | P1 | a=7.244 b=8.039 c=8.848 α=92.16° β=92.73° γ=96.21° | | | |
| bpy=bipyridine | [Fe(bpy)$_3$]$_2$[NbO(C$_2$O$_4$)$_3$]Cl·11H$_2$O | | | | | | |
| | [Fe(bpy)$_3$]$_2$[NbO($_2$O$_4$)$_3$]Cl·12H$_2$O | orthorhombic | P2$_1$2$_1$2$_1$ | a=14.975 b=21.708 c=22.351 Z=4 | 7266 | 1.530 | dark red |
| | [Co(bpy)$_3$]$_2$[NbO(C$_2$O$_4$)$_3$]Cl·11H$_2$O | monoclinic | P2$_1$/c | a=23.548 b=13.631 c=22.812 β=101.04 | 7187 | 1.536 | orange red |
| | [Co(bpy)$_3$]$_2$[NbO(C$_2$O$_4$)$_3$]Cl·12H$_2$O | orthorhombic | P2$_1$2$_1$2$_1$ | a=15.103 b=22.075 c=22.386 Z=4 | 7463 | 1.495 | brown |
| | [Ni(bpy)$_3$]$_2$[NbO(C$_2$O$_4$)$_3$]Cl·11H$_2$O | monoclinic | P2$_1$/c | a=23.875 b=13.265 c=23.115 β=101.69 Z=4 | 7169 | 1.539 | pink |
| | [Ni(bpy)$_3$]$_2$[NbO(C$_2$O$_4$)$_3$]Cl·12H$_2$O | orthorhombic | P2$_1$2$_1$2$_1$ | 15.058 b=22.039 c=22.398 Z=4 | 7433 | 1.500 | dark pink |
| | [Cu(bpy)$_3$]$_2$[NbO(C$_2$O$_4$)$_3$]Cl·12H$_2$O | orthorhombic | P2$_1$2$_1$2$_1$ | a=15.035 b=22.267 c=22.538 Z=4 | 7545 | 1.487 | blue |
| | [Zn(bpy)$_3$]$_2$[NbO(C$_2$O$_4$)$_3$]Cl·11H$_2$O | monoclinic | P2$_1$/c | 24.070 b=13.332 c=23.168 β=102.19 Z=4 | 7267 | 1.530 | pink |
| | [Zn(bpy)$_3$]$_2$[NbO(C$_2$O$_4$)$_3$]Cl·12H$_2$O | | | | | | |
| tris(Tetraethylammonium) tetrakis(μ$_3$-sulfido)-(oxalato-O,O')-trichloro-cyano-tri-iron-molybdenum | (Et$_4$N)$_5${[C$_2$O$_4$)MoFe$_3$S$_4$Cl$_2$]$_2$(μ-CN)(μ-S)} | monoclinic | P2$_1$/n | a=10.331 b=22.580 c=19.083 β=91.97° | | | double cubane structure |
| (μ$_2$-Oxalato)-dichloro-bis(η$^6$-p-cymene)-di-ruthenium | [Ru$_2$(μ-η$^4$-C$_2$O$_4$)Cl$_2$(η$^6$-p-Pr$^i$C$_6$H$_4$Me)$_2$] | monoclinic | P2$_1$/n | a=7.571 b=8.998 c=16.528 β=95.52° Z=2 | 1120.73 | | yellow |
| chloro-(oxalato)-tris(pyridine)-rhodium | mer-[Rh(C$_2$O$_4$)Cl(py)$_3$] | orthorhombic | P2$_1$2$_1$2$_1$ | a=9.9999 b=12.0930 c=14.9368 Z=4 | 1806.2 | 1.705 | yellow |
| CHLOROPENTAAMMINECHROMIUM(III) BIS(OXALATO)PALLADATE | [Cr(NH$_3$)$_5$Cl][Pd(C$_2$O$_4$)$_2$] | triclinic | | a = 3.225 b = 10.290 c = 11.390 α = 116.5° β = 97.9° γ = 91.2° | 334.5 | | |
| | C(NH$_2$)$_3$Cd(C$_2$O$_4$)Cl(H$_2$O)·H$_2$O | triclinic | P1 | a=6.8136 b=7.4890 c=10.0515 α=84.082° β=77.806° γ=88.813° | | | band gap 3.76 eV |
| | SnC$_2$O$_4$Cl$_2$ | | | | | | |
| | SnC$_2$O$_4$Cl$_2$ . CuBr$_2$ 1/4EtOH | | | | | | green |
| | SnC$_2$O$_4$Cl$_2$ . CuCl$_2$ . H$_2$O | | | | | | green |
| | SnC$_2$O$_4$Cl$_2$ . CoBr2 1/8EtOH | | | | | | rose colour |
| | (Et$_4$N)$_2$C$_2$O$_4$ . SnCl$_2$F$_2$ . 2H$_2$O: | | | | | | white |
| | (Me$_4$N)$_2$Sn(C$_2$O$_4$)Cl$_2$ | | | | | | white |
| | (Et$_4$N)$_2$Sn(C$_2$O$_4$)Cl$_2$ .(Et$_4$N)$_2$C$_2$O$_4$(SnCl$_4$)$_2$ . EtOH | | | | | | white |
| | Sn(C$_2$O$_4$)$_2$ . 2[SnCl$_4$ . (Pyridine)$_2$] | | | | | | white |
| | (Et$_4$N)$_2$SnCl$_6$ . (Et$_4$N)$_2$C$_2$O$_4$ . 2SnC$_2$O$_4$(OH)$_2$ | | | | | | white |
| | (NH$_4$)$_2$Sb(C$_2$O$_4$)Cl$_3$ | orthorhombic | P2$_1$2$_1$2$_1$ | a=8.6961 b=8.7844 c=13.5956 Z=4 | 1038.57 | 2.253 | |
| | K$_2$Sb(C$_2$O$_4$)Cl$_3$ | orthorhombic | P2$_1$2$_1$2$_1$ | a=8.3966 b=8.6023 c=13,6342 Z=4 | 984.80 | 2.660 | |
| | Rb$_2$Sb(C$_2$O$_4$)Cl$_3$ | orthorhombic | P2$_1$2$_1$2$_1$ | a=8.6769 b=8.8485 c=13.8014 Z=4 | 1059.64 | 3.053 | birefringence 0.22@546 nm;NLO 2.1 × KH$_2$PO$_4$ |
| | Ba$_2$Mn$_2$Cl$_2$(C$_2$O$_4$)$_3$·4H$_2$O | monoclinic | C2/c | a=22.916 b=8.248 c=9.904 β=99.53° | | | |
| | Ba$_2$Fe$_2$Cl$_2$(C$_2$O$_4$)$_3$·4H$_2$O | monoclinic | C2/c | a=22.798 b=8.297 c=9.849 β=99.90° | | | |
| | Ba$_2$Co$_2$Cl$_2$(C$_2$O$_4$)$_3$·4H$_2$O | monoclinic | C2/c | a=22.675 b=8.230 c=9.757 β=100.00° | | | purple |
| | BaCd(C$_2$O$_4$)$_{1.5}$Cl(H$_2$O)$_2$ | monoclinic | C2/c | a=23.101 b=8.253 c=10.040 β 99.14° | | | band gap 4.53 eV |
| | La(C$_2$O$_4$)Cl | monoclinic | P2$_1$/n | a=8.489 b=16.19 c=5.880 β=104.14° | | | |
| | La(C$_2$O$_4$)Cl·3H$_2$O | | | | | | |
| | Ce(C$_2$O$_4$)Cl | | | | | | |
| | Ce(C$_2$O$_4$)Cl·3H$_2$O | | | | | | |
| | Pr(C$_2$O$_4$)Cl·3H$_2$O | | | | | | stable to 163°C |
| | Nd(C$_2$O$_4$)Cl·3H$_2$O | | | | | | stable to 167°C; dec 510° to NdOCl |
| | Sm(C$_2$O$_4$)Cl·3H$_2$O | | | | | | stable to 174°C; dec at 347° to EuC$_2$O$_4$ |
| | Eu(C$_2$O$_4$)Cl·3H$_2$O | | | | | | stable to 178°C |
| | Gd(C$_2$O$_4$)Cl·3H$_2$O | | | | | | |
| | (Et$_4$N)$_2$Sn(C$_2$O$_4$)Cl$_2$ . (Et$_4$N)$_2$C$_2$O$_4$(SnCl$_4$)$_2$ . EtOH | | | | | | |
| | [(Me$_4$N)$_2$C$_2$O$_4$SnCl$_4$]$_2$ . [(Me$_4$N)$_2$Sn(C$_2$O$_4$)$_2$Cl$_2$]$_2$ . Sn(WO$_4$)$_2$ | | | | | | |
| | [Pt(HC$_2$O$_4$)Cl$_3$]$^{2−}$ | | | | | | |
| | [Pt(HC$_2$O$_4$)(C$_2$O$_4$)Cl]$^{2−}$ | | | | | | |
| | K$_2$[Pt(C$_2$O$_4$)Cl$_2$]·H$_2$O | triclinic | P1 | a=7.136 b=7.308 c=10.130 α=86.75° β=74.58° γ=54.28° Z=2 | 457.7 | 3.27 | |
| | [Pt(NH$_3$)$_5$Cl][Cr(C$_2$O$_4$)$_3$] · 4H$_2$O | orthorhombic | Pccn | a=38.901 b=13.7267 c=14.9141 | | | |
| | [Pt(NH$_3$)$_5$Cl][Fe(C$_2$O$_4$)$_3$] · 4H$_2$O | orthorhombic | Pccn | a=39.0123 b=13.7232 c=14.8990 | | | |
| | [Pt(NH$_3$)$_5$Cl][Co(C$_2$O$_4$)$_3$] · 2H$_2$O | monoclinic | P2$_1$ | a=8.5158 b=12.6409 c=8.5726 β=105.000° | | | |
| lead chloride oxalate | Pb$_2$Cl$_2$(C$_2$O$_4$) | monoclinic | C2/m | a=5.9411 b=5.8714 c=9.4212 β=95.232° Z=2 | 327.26 | 5.82 | dec 350°C to Pb, Pb$_5$O$_2$Cl$_6$ and Pb$_3$O$_2$Cl$_2$ |
| | Th$_4$Cl$_4$(C$_2$O$_4$)$_6$•20H$_2$O | | | | | | |
| Plutonium(III) oxalato chloride | ?Pu(C$_2$O$_4$)Cl·3H$_2$O | | | | | | blue; biaxial (−) |
| | Am(C$_2$O$_4$)Cl·3H$_2$O | monoclinic | P2$_1$/n | a=5.852 b=15.823 c=8.351 β=104.243° | | | |