Supporting Materials

Supporting materials

Table S1. The Cartesian coordinates of all six complexes of alizarin with three alkali metal hydroxides with explicit methanol molecules a. First form of the alizarin complex with LiOH and three methanol molecules

Li 2.39905700 0.03190600 0.43273300 O 3.28110200 0.69048000 -1.28723200 H 2.79396600 1.51914700 -1.15185500 O 3.07088500 0.88272300 2.16013400 H 2.42135000 1.57804200 1.96221300 O 1.78923000 -2.59197000 -1.46248700 H 1.09462600 -2.10520000 -0.98447700 O 3.37634200 -1.74958600 0.54189600 H 2.95978700 -2.19561900 -0.22976900 C -1.51722100 -2.53214000 0.43103400 C -1.74172000 -1.17107800 0.20352700 C -0.58739400 -0.23707400 0.16818300 C -3.05683000 -0.71247700 0.02204000 C -3.33691100 0.72990500 -0.17955200 C -2.19444200 1.65243800 -0.12463600 C -0.85233700 1.17852000 0.05935500 C -2.58069100 -3.42622600 0.46030900 C -4.11935700 -1.61735500 0.04627600 C -2.45229600 3.00469800 -0.26227500 C 0.20987600 2.12135000 0.10582300 C -0.12763600 3.52372900 -0.03762100 C -1.42079300 3.95383000 -0.21875000 H -3.47938400 3.32242100 -0.40628000 H -1.62909400 5.01402700 -0.32423200 C -3.88488600 -2.96975500 0.26169800 H -0.50290200 -2.87939000 0.59562000 H -2.39464200 -4.48061900 0.64057000 H -5.12537200 -1.23872800 -0.10166400 H -4.71522700 -3.66900200 0.28176900 O 0.56560300 -0.72227800 0.23480400 O 1.46217200 1.87995000 0.27293500 O -4.49118900 1.11956200 -0.36798100 O 0.91282600 4.36447200 0.01777500 H 1.67940400 3.76565800 0.15407300 C 4.67054500 0.97191800 -1.39938500 H 5.19092000 0.01469000 -1.46518400 H 4.88705900 1.55270000 -2.30245700 H 5.04560000 1.51671500 -0.52528500 C 3.10756600 -2.54109700 1.69016800 H 3.60067200 -3.51804700 1.62741000 H 3.49906900 -2.01148300 2.56157100 H 2.03041000 -2.69667400 1.82973100 C 1.39149800 -3.94767200 -1.61365900 H 0.47599900 -4.02989000 -2.21022100 H 2.19671000 -4.46745300 -2.13675700 H 1.22851700 -4.43760600 -0.64630300 H 2.76777700 0.47467500 2.97935400 b. Second form of the alizarin complex with LiOH and three methanol molecules

Li -3.68179600 0.09828600 -0.73600100 O -4.49094400 1.89610300 -1.11464200 H -3.73193300 2.19437700 -0.58180100 O -2.84254000 -0.82692000 -2.23828200 H -2.01038500 -1.04408100 -1.77824700 O -2.54547400 -2.15995900 1.51840100 H -1.88548700 -1.80859100 0.89220200 O -4.71419900 -1.07833700 0.41316500 H -3.98533500 -1.54720800 0.89249200 C 4.33346600 -1.91167800 -0.57720900 C 3.52371200 -0.80798400 -0.29740700 C 2.05781100 -0.95383300 -0.34155900 C 4.10714400 0.43078300 0.02313800 C 3.27190100 1.62858600 0.32612900 C 1.82526800 1.46593800 0.27722000 C 1.23234300 0.21376000 -0.04581500 C 5.71695500 -1.78805600 -0.53932500 C 5.49657000 0.54259600 0.05843900 C 0.98713700 2.54737300 0.54844500 C -0.15703500 0.09009900 -0.08626400 C -1.03396100 1.20088700 0.19300700 C -0.39290500 2.42187500 0.50889500 H 1.44162300 3.50247000 0.79401400 H -1.02858700 3.27643100 0.72491700 C 6.29809000 -0.55943200 -0.22099100 H 3.86404400 -2.85864000 -0.82254800 H 6.34399000 -2.64700600 -0.75720500 H 5.93354800 1.50393300 0.30779200 H 7.37918600 -0.46256600 -0.19113300 O 1.54383500 -2.05433700 -0.62717700 O -0.74190300 -1.09311500 -0.39166500 O 3.81256200 2.70355000 0.60422200 O -2.30851000 1.05979500 0.15746000 C -5.69341000 2.36093300 -0.51212500 H -6.52593400 1.94584500 -1.08337300 H -5.77949400 2.02831600 0.52867200 H -5.75546800 3.45377500 -0.54491800 C -2.25830500 -1.61617200 2.80120300 H -1.27291400 -1.93924400 3.15519900 H -2.29282200 -0.52068000 2.79417800 H -3.01661200 -1.98728700 3.49359900 C -5.58817000 -2.04548500 -0.15266500 H -6.02962100 -2.68172200 0.62203000 H -6.39311200 -1.51168400 -0.66300000 H -5.07242300 -2.68210100 -0.88255000 H -3.22451000 -1.67615400 -2.48863800 H 0.02535900 -1.72842000 -0.55423400 c. First form of the alizarin complex with NaOH and three methanol molecules

Na -2.27592700 -0.55326300 -0.28634700 O -3.83590200 1.26731000 -0.61443100 H -3.01271700 1.76115600 -0.48348400 O -1.94897500 -0.82184800 -2.63690100 H -1.12264100 -1.21808800 -2.92913900 O -2.99515300 -1.03891200 2.09110200 H -2.23158400 -1.12550800 2.66943600 O -3.46147600 -2.66486100 -0.06023700 H -3.42417700 -2.46408800 0.88757100 C 2.14359400 -2.66341900 0.03943000 C 2.25961800 -1.27234300 0.03974200 C 1.01864600 -0.44546300 0.08146600 C 3.53266400 -0.69060600 -0.00707400 C 3.68640700 0.78205400 -0.00454000 C 2.46309600 1.59377100 0.06685000 C 1.15900800 0.99931600 0.09884200 C 3.27577400 -3.46421200 -0.00468300 C 4.66799600 -1.50151500 -0.05410300 C 2.61790500 2.96748700 0.10658100 C 0.01173900 1.84428900 0.16372600 C 0.25351900 3.27273700 0.22552500 C 1.51098900 3.81876200 0.19143300 H 3.61881600 3.38145900 0.07788000 H 1.63520100 4.89600600 0.23385400 C 4.54251200 -2.88249600 -0.05250400 H 1.15445500 -3.10528000 0.07491600 H 3.17417100 -4.54454200 -0.00307000 H 5.64485200 -1.03269000 -0.09078200 H 5.42804000 -3.50834500 -0.08824900 O -0.06905900 -1.03407800 0.10349900 O -1.21668500 1.49343000 0.18675400 O 4.80719700 1.28741300 -0.05604000 O -0.84750500 4.03376500 0.31763700 H -1.57847600 3.38412400 0.34178300 C -4.46960900 1.72119400 -1.80081800 H -5.37003900 1.12085300 -1.94100200 H -4.76058500 2.77433600 -1.72200400 H -3.82419600 1.59449200 -2.67687600 C -2.95036200 -3.97006600 -0.28519600 H -3.56511300 -4.73189600 0.20639600 H -2.96922100 -4.14896200 -1.36153500 H -1.91683400 -4.06551900 0.06666600 C -4.02189700 -0.33872500 2.79093400 H -3.70221000 0.67633600 3.04420200 H -4.88289700 -0.28361000 2.12452200 H -4.30997600 -0.86913600 3.70322200 H -2.61880000 -1.20753700 -3.20923600 d. Second form of the alizarin complex with NaOH and three methanol molecules

Na -3.17895200 -0.12758100 -0.81486900 O -4.07958400 2.06484900 -1.23399900 H -3.40297600 2.25991600 -0.55930200 O -3.19078300 -0.98973400 -2.95565100 H -3.24637600 -0.43844200 -3.74204800 O -2.15609400 -2.04545500 2.12418900 H -1.55810100 -1.60174200 1.50616800 O -4.33988600 -1.57182600 0.56369400 H -3.67690400 -1.84820900 1.22838300 C 4.12223600 -2.04790900 -0.76934900 C 3.44844700 -0.88469500 -0.39430000 C 1.97539800 -0.88416600 -0.34483400 C 4.17292500 0.27324800 -0.06881300 C 3.48543500 1.53266200 0.33586300 C 2.03428700 1.51817600 0.37751000 C 1.29767000 0.34341500 0.05600500 C 5.50840800 -2.06475100 -0.82260000 C 5.56493100 0.24410700 -0.12631600 C 1.32959100 2.66606600 0.73916600 C -0.09317000 0.36551600 0.11061500 C -0.83254100 1.55248800 0.46736400 C -0.05387800 2.68874100 0.78312500 H 1.89167800 3.56072000 0.98601200 H -0.57880900 3.59779500 1.06122200 C 6.22976500 -0.91634400 -0.50061900 H 3.54771300 -2.93314800 -1.01698600 H 6.02858400 -2.97069900 -1.11455700 H 6.11710900 1.14221700 0.12563700 H 7.31385800 -0.92765200 -0.54239700 O 1.33458300 -1.90606300 -0.64318600 O -0.83864600 -0.72390500 -0.17314700 O 4.15236300 2.53171300 0.61815000 O -2.10999600 1.52098500 0.47715300 C -5.29802200 2.69963500 -0.87904000 H -6.04374800 2.42696800 -1.62785600 H -5.65365800 2.37034100 0.10392700 H -5.19388800 3.79019400 -0.87117900 C -2.04131000 -1.42045200 3.39911700 H -1.02718900 -1.52381100 3.79699000 H -2.30295000 -0.35865300 3.34812600 H -2.73678300 -1.92471700 4.07101200 C -5.13794400 -2.68890400 0.20154200 H -5.70007300 -3.07146000 1.06023000 H -5.84758500 -2.35870500 -0.55912600 H -4.53065300 -3.50015100 -0.21529100 H -2.69170900 -1.76405100 -3.23221000 H -0.18810100 -1.42883700 -0.44741200 e. First form of the alizarin complex with KOH and three methanol molecules

K -2.33100200 -0.00965400 -0.07572400 O -4.67978100 1.49176500 -0.15428300 H -4.73452200 2.40505200 -0.45591400 O -2.66869600 -0.24410600 -2.84560300 H -2.29608200 -1.02449200 -3.27072600 O -2.79879400 -0.19624000 2.66961500 H -2.39151400 -0.91746900 3.16147700 O -3.85734300 -2.30698400 -0.00526200 H -4.15772800 -2.76920300 0.78444600 C 2.11623200 -2.84572900 0.06751100 C 2.46677200 -1.49329200 0.03492200 C 1.38138600 -0.46572000 -0.00279800 C 3.82384200 -1.13708700 0.03873300 C 4.23139400 0.28777200 0.00495500 C 3.16419100 1.29633800 -0.03128200 C 1.77332100 0.93008400 -0.03480700 C 3.09741700 -3.82888700 0.10344200 C 4.80654400 -2.13030500 0.07477200 C 3.55441600 2.62496200 -0.06261900 C 0.79152400 1.96476400 -0.07066200 C 1.27824800 3.34116500 -0.10204400 C 2.61236900 3.66506300 -0.09862400 H 4.61594500 2.84904700 -0.05897700 H 2.92349600 4.70530100 -0.12305400 C 4.44788500 -3.47128500 0.10703900 H 1.06323500 -3.10766800 0.06453200 H 2.81304100 -4.87683500 0.12868500 H 5.84867500 -1.82744300 0.07675900 H 5.21497900 -4.23943900 0.13484800 O 0.20441800 -0.86080700 -0.00486900 O -0.47833500 1.86073500 -0.07952100 O 5.42943100 0.58940600 0.00805000 O 0.29433800 4.24802000 -0.13466300 H -0.50333200 3.65797700 -0.12557200 C -5.72138900 0.75877300 -0.78131600 H -5.61558100 -0.27955000 -0.45889400 H -6.71316700 1.12148400 -0.48508000 H -5.64660500 0.79274500 -1.87583700 C -4.22805400 -3.07512000 -1.13853700 H -5.31489700 -3.20630100 -1.20831100 H -3.88642400 -2.52321800 -2.01663300 H -3.75286000 -4.06380600 -1.13877300 C -4.17991100 -0.17119600 2.99675300 H -4.34615400 0.06958700 4.05398700 H -4.63785600 0.60661400 2.38196000 H -4.67373500 -1.12507700 2.77105000 H -3.57888700 -0.22000100 -3.16153300 f. Second form of the alizarin complex with KOH and three methanol molecules

K 3.08362100 0.08960700 -0.27345000 O 5.63320300 -0.96046500 -0.25097500 H 5.89949100 -1.88532800 -0.29153300 O 3.28709200 0.97318900 -2.88766500 H 2.89935200 1.81964900 -3.13625300 O 3.15420400 -0.71768000 2.42271000 H 2.30770900 -0.59560500 2.86679800 O 4.18647100 2.50920900 0.43030500 H 4.52879800 2.74620900 1.29897400 C -4.39123400 2.37310700 0.56423000 C -3.85672400 1.11821000 0.25793900 C -2.39413800 0.95695900 0.14920300 C -4.71157500 0.01954800 0.05615500 C -4.17980200 -1.33621300 -0.27085900 C -2.74484400 -1.47313200 -0.37897000 C -1.86898300 -0.36017800 -0.17443900 C -5.76608700 2.54041400 0.66958700 C -6.09109400 0.20065200 0.16464700 C -2.17503700 -2.71214000 -0.68976500 C -0.48671900 -0.52660600 -0.28394300 C 0.11800300 -1.81687000 -0.61130000 C -0.80667500 -2.88297500 -0.80269500 H -2.84298700 -3.55498000 -0.84485300 H -0.39268600 -3.85803800 -1.04764800 C -6.61689500 1.45117100 0.46881900 H -3.71441400 3.20745300 0.71675000 H -6.17750900 3.51660700 0.90743900 H -6.73716300 -0.65659800 0.00575700 H -7.69203500 1.58088500 0.55075400 O -1.64082600 1.93851900 0.33294600 O 0.36084700 0.49226000 -0.09635100 O -4.97017800 -2.27929600 -0.43544100 O 1.37398600 -1.93454800 -0.70674100 C 6.49491600 -0.29271800 0.65984800 H 6.13143600 0.73406500 0.74427100 H 6.47293700 -0.75293100 1.65526500 H 7.53124100 -0.27208300 0.30167800 C 3.40761100 -2.11515500 2.36234100 H 3.52322300 -2.55358900 3.36075300 H 2.61479900 -2.64910700 1.82470000 H 4.34226000 -2.24427900 1.81166900 C 4.84616000 3.31141400 -0.53806300 H 5.93459800 3.18068400 -0.50384400 H 4.48820800 2.98388200 -1.51644300 H 4.61268800 4.37581100 -0.41533300 H 4.16118300 0.99132400 -3.29295600 H -0.21962400 1.28099100 0.11289200