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Single crystals of the aluminium and gallium com­plexes of 6,6′-{(1E,1′E)-[1,2-phenyl­enebis(aza­nylyl­idene)]bis­(methanylyl­idene)}bis­(2-meth­oxy­phenol), namely di­aqua­(6,6′-{(1E,1′E)-[1,2-phenyl­enebis(aza­nylyl­idene)]bis­(methanylyl­idene)}bis­(2-meth­oxy­phenolato)-κ4O1,N,N′,O1′)aluminium(III) nitrate ethanol monosolvate, [Al(C22H18N2O4)(H2O)2]NO3·C2H5OH, 1, and di­aqua­(6,6′-{(1E,1′E)-[1,2-phenyl­enebis(aza­nylyl­idene)]bis­(methanylyl­idene)}bis­(2-meth­oxy­phenolato)-κ4O1,N,N′,O1′)gallium(III) nitrate ethanol monosolvate, [Ga(C22H18N2O4)(H2O)2]NO3·C2H5OH, 2, were obtained after successful synthesis in ethanol. Both com­plexes crystallized in the triclinic space group P\overline{1}, with two mol­ecules in the asymmetric unit. In both structures, in one of the independent molecules the tetradentate ligand is almost planar while in the other independent molecule the ligand shows significant distortions from planarity, as illustrated by the largest distance from the plane constructed through the central metal atom and the O,N,N′,O′-coordinating atoms of the ligand in 1 of 1.155 (3) Å and a distance of 1.1707 (3) Å in 2. The possible reason for this is that there are various strong π-inter­actions in the structures. This was confirmed by density functional theory (DFT) calculations, as were the other crystallographic data. DFT was also used to predict the outcome of cyclic voltammetry experiments. Ligand oxidation is more stabilized in the gallium complex. Solid-state photoluminescence gave an 80 nm red-shifted spectrum for the gallium com­plex, whereas the aluminium complex maintains the ligand curve with a smaller red shift of 40 nm.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619008805/qf3029sup1.cif
Contains datablocks shelx, 16rjt1_0m, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619008805/qf3029shelxsup2.hkl
Contains datablock shelx

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619008805/qf302916rjt1_0msup3.hkl
Contains datablock 16rjt1_0m

CCDC references: 1935699; 1935698

Computing details top

For both structures, data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXTL (Bruker, 2010); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015).

Diaqua(6,6'-{(1E,1'E)-[1,2-phenylenebis(azanylylidene)]bis(methanylylidene)}bis(2-methoxyphenolato)-κ4O1,N,N',O1')aluminium(III) nitrate ethanol monosolvate (shelx) top
Crystal data top
[Al(C22H18N2O4)(H2O)2]NO3·C2H6OZ = 4
Mr = 545.47F(000) = 1144
Triclinic, P1Dx = 1.476 Mg m3
a = 12.413 (5) ÅMo Kα radiation, λ = 0.71069 Å
b = 13.394 (5) ÅCell parameters from 9867 reflections
c = 16.368 (5) Åθ = 1.0–1.0°
α = 87.899 (5)°µ = 0.15 mm1
β = 79.578 (5)°T = 100 K
γ = 66.635 (5)°Cuboid, yellow
V = 2455.1 (15) Å30.30 × 0.27 × 0.13 mm
Data collection top
Bruker APEXII CCD
diffractometer
Rint = 0.062
φ and ω scansθmax = 28.0°, θmin = 1.7°
64029 measured reflectionsh = 1612
11817 independent reflectionsk = 1717
7331 reflections with I > 2σ(I)l = 2121
Refinement top
Refinement on F219 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.056H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.163 w = 1/[σ2(Fo2) + (0.0684P)2 + 2.3877P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
11817 reflectionsΔρmax = 0.80 e Å3
718 parametersΔρmin = 0.76 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.5080 (2)0.3196 (2)0.35492 (16)0.0242 (6)
C5A0.9140 (2)0.1954 (2)0.08411 (17)0.0224 (6)
C1T0.0336 (4)0.2269 (4)0.5388 (3)0.0752 (14)
H1T10.10420.16910.55280.090*
H1T20.00570.19710.49790.090*
C4A0.8417 (3)0.1404 (2)0.07802 (19)0.0297 (6)
H4A0.83700.11800.02620.036*
C20.5570 (3)0.3951 (2)0.32735 (18)0.0309 (7)
H20.58620.42500.36400.037*
C2T0.0622 (4)0.2631 (4)0.6162 (3)0.0695 (12)
H2TA0.03980.30090.65440.104*
H2TB0.07090.20050.64200.104*
H2TC0.13660.31070.60130.104*
C30.5619 (3)0.4253 (2)0.24553 (19)0.0345 (7)
H30.59350.47630.22760.041*
C3A0.7767 (3)0.1189 (2)0.1491 (2)0.0351 (7)
H3A0.72830.08180.14510.042*
C40.5199 (3)0.3800 (2)0.18989 (18)0.0343 (7)
H40.52560.39930.13460.041*
C2A0.7835 (3)0.1526 (2)0.2262 (2)0.0349 (7)
H2A0.74040.13690.27380.042*
C1A0.8534 (3)0.2090 (2)0.23351 (18)0.0282 (6)
H1A0.85640.23220.28560.034*
C50.4696 (3)0.3064 (2)0.21672 (18)0.0319 (7)
H50.44200.27580.17940.038*
C20A0.9197 (2)0.2309 (2)0.16182 (17)0.0226 (6)
C60.4603 (2)0.2781 (2)0.29950 (17)0.0255 (6)
C70.3410 (3)0.1778 (2)0.29453 (17)0.0265 (6)
H70.33400.20310.24130.032*
C19A1.0190 (2)0.3174 (2)0.22613 (16)0.0228 (6)
H19A0.99330.29170.27620.027*
C18A1.0854 (2)0.3842 (2)0.22816 (16)0.0223 (6)
C80.2809 (2)0.1087 (2)0.32543 (17)0.0243 (6)
C17A1.1076 (3)0.4048 (2)0.30642 (18)0.0320 (7)
H17A1.08370.37190.35310.038*
C90.2189 (3)0.0800 (2)0.27187 (18)0.0280 (6)
H90.21800.10700.21870.034*
C16A1.1634 (3)0.4719 (3)0.31399 (19)0.0375 (7)
H16A1.17950.48310.36540.045*
C100.1608 (3)0.0138 (2)0.29680 (19)0.0319 (7)
H100.12010.00390.26110.038*
C110.1625 (3)0.0279 (2)0.37686 (18)0.0304 (6)
H110.12260.07300.39410.036*
C15A1.1970 (3)0.5246 (2)0.24454 (18)0.0312 (7)
H15A1.23400.57160.25030.037*
C14A1.1755 (2)0.5069 (2)0.16792 (16)0.0232 (6)
C120.2228 (2)0.0021 (2)0.42984 (17)0.0264 (6)
C13A1.1224 (2)0.4335 (2)0.15751 (15)0.0189 (5)
C130.2825 (2)0.0675 (2)0.40557 (16)0.0226 (6)
C140.4968 (2)0.1922 (2)0.60431 (16)0.0224 (6)
C12A1.1073 (2)0.2922 (2)0.13148 (16)0.0206 (5)
C11A1.1604 (2)0.3190 (2)0.20851 (16)0.0230 (6)
C150.5028 (2)0.1578 (2)0.68710 (16)0.0227 (6)
C10A1.1856 (3)0.2562 (2)0.27980 (18)0.0341 (7)
H10A1.22330.27340.32940.041*
C160.5523 (3)0.1992 (2)0.73854 (17)0.0276 (6)
H160.55590.17530.79240.033*
C9A1.1544 (3)0.1664 (3)0.2774 (2)0.0429 (8)
H9A1.17380.12270.32510.051*
C170.5973 (3)0.2776 (2)0.70969 (18)0.0307 (6)
H170.63060.30570.74460.037*
C8A1.0957 (3)0.1423 (2)0.20543 (19)0.0370 (7)
H8A1.07150.08480.20530.044*
C180.5923 (3)0.3129 (2)0.63031 (17)0.0279 (6)
H180.62250.36480.61180.034*
C7A1.0715 (2)0.2045 (2)0.13123 (17)0.0254 (6)
C190.5422 (2)0.2716 (2)0.57628 (16)0.0229 (6)
C6A1.0075 (2)0.1765 (2)0.05780 (17)0.0236 (6)
H6A0.98140.12120.06300.028*
C200.5427 (2)0.3105 (2)0.49339 (17)0.0242 (6)
H200.57480.36230.47960.029*
C0211.2292 (3)0.4467 (2)0.28041 (17)0.0296 (6)
H02A1.30740.39450.30330.044*
H02B1.23320.51540.27080.044*
H02C1.17640.45540.31880.044*
C210.1731 (3)0.1105 (3)0.5381 (2)0.0380 (7)
H21A0.08860.07240.54110.057*
H21B0.18920.13410.59230.057*
H21C0.20230.17260.50040.057*
C220.4375 (3)0.0573 (3)0.79402 (17)0.0331 (7)
H22A0.51260.02590.81270.050*
H22B0.39930.00690.80150.050*
H22C0.38740.12350.82570.050*
C0221.2547 (3)0.6319 (2)0.10115 (19)0.0314 (7)
H02D1.20200.68980.14030.047*
H02E1.26690.66110.04750.047*
H02F1.32990.59660.11920.047*
N010.99260 (19)0.29061 (16)0.15943 (13)0.0201 (5)
N020.98374 (19)0.22294 (16)0.01499 (13)0.0201 (5)
N030.5016 (2)0.27866 (17)0.43608 (13)0.0225 (5)
N040.4048 (2)0.20796 (17)0.33505 (14)0.0242 (5)
N071.2872 (2)0.06382 (18)0.07667 (15)0.0290 (5)
N080.7856 (2)0.43557 (19)0.45715 (14)0.0286 (5)
O11.09202 (16)0.35187 (13)0.06456 (11)0.0204 (4)
O1A0.0628 (2)0.3039 (3)0.5058 (2)0.0765 (9)
H1AA0.00250.35650.49950.115*
O21.10899 (16)0.41676 (14)0.08147 (10)0.0203 (4)
O31.20306 (17)0.55492 (14)0.09594 (11)0.0249 (4)
O41.18555 (16)0.40955 (14)0.20349 (11)0.0238 (4)
O51.20062 (17)0.20279 (15)0.04417 (13)0.0256 (4)
O60.89451 (16)0.44340 (14)0.05168 (11)0.0199 (4)
O70.33834 (17)0.08916 (14)0.46022 (11)0.0245 (4)
O80.44928 (17)0.14838 (14)0.55821 (11)0.0248 (4)
O90.45715 (17)0.08044 (15)0.70789 (11)0.0259 (4)
O100.23163 (18)0.03909 (15)0.50890 (12)0.0295 (4)
O110.2739 (2)0.30139 (17)0.48967 (13)0.0324 (5)
O120.57291 (18)0.05570 (15)0.40929 (12)0.0251 (4)
O130.6790 (2)0.49714 (18)0.47098 (16)0.0496 (6)
O140.8200 (2)0.34409 (16)0.42420 (13)0.0372 (5)
O150.8595 (2)0.4692 (2)0.47657 (15)0.0478 (6)
O161.18516 (17)0.01059 (15)0.07687 (13)0.0325 (5)
O181.2986 (2)0.15766 (16)0.09207 (15)0.0413 (6)
Al11.05248 (7)0.32514 (6)0.04415 (5)0.01802 (17)
Al20.41964 (7)0.17640 (6)0.45372 (5)0.02215 (19)
C4R1.4110 (4)0.3722 (3)0.0676 (2)0.0651 (12)
H4R11.42610.43380.05340.098*
H4R21.33240.39680.08060.098*
H4R31.46890.33300.11490.098*
O4T1.4043 (5)0.2113 (3)0.0212 (3)0.0478 (6)0.5
H4T1.46490.16960.05120.072*0.5
C4T1.4190 (11)0.3067 (5)0.0030 (6)0.0478 (6)0.5
H4T11.35850.34600.04400.057*0.5
H4T21.49640.28680.01270.057*0.5
O4U1.4144 (5)0.2145 (3)0.0158 (3)0.0496 (6)0.5
H4U1.44710.17960.02830.074*0.5
C4U1.4270 (10)0.3121 (6)0.0117 (6)0.0496 (6)0.5
H4U11.50610.29890.02190.059*0.5
H4U21.37000.35980.05680.059*0.5
O171.37647 (19)0.04004 (17)0.06044 (16)0.0444 (6)
H521.203 (3)0.1372 (18)0.049 (2)0.048 (10)*
H511.269 (2)0.200 (4)0.021 (3)0.097 (18)*
H610.879 (3)0.461 (3)0.0022 (14)0.056 (12)*
H620.891 (3)0.500 (2)0.077 (2)0.049 (11)*
H11B0.205 (2)0.301 (3)0.494 (2)0.061 (13)*
H11A0.269 (4)0.364 (2)0.496 (3)0.071 (14)*
H12B0.563 (3)0.003 (2)0.389 (2)0.045 (10)*
H12A0.620 (3)0.028 (3)0.443 (2)0.081 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0277 (14)0.0180 (13)0.0214 (14)0.0039 (11)0.0039 (11)0.0037 (10)
C5A0.0218 (13)0.0152 (12)0.0275 (14)0.0058 (10)0.0028 (11)0.0080 (10)
C1T0.057 (3)0.085 (3)0.057 (3)0.001 (3)0.009 (2)0.007 (3)
C4A0.0304 (16)0.0283 (15)0.0336 (16)0.0148 (13)0.0068 (12)0.0061 (12)
C20.0418 (18)0.0234 (14)0.0290 (15)0.0134 (13)0.0101 (13)0.0061 (12)
C2T0.065 (3)0.061 (3)0.075 (3)0.020 (2)0.006 (2)0.003 (2)
C30.0456 (19)0.0253 (15)0.0347 (17)0.0170 (14)0.0075 (14)0.0119 (13)
C3A0.0359 (17)0.0332 (16)0.0422 (18)0.0223 (14)0.0028 (14)0.0085 (14)
C40.0455 (19)0.0335 (16)0.0252 (15)0.0163 (14)0.0107 (13)0.0143 (13)
C2A0.0341 (17)0.0338 (16)0.0363 (17)0.0180 (14)0.0033 (13)0.0104 (13)
C1A0.0313 (16)0.0252 (14)0.0271 (15)0.0125 (12)0.0011 (12)0.0086 (12)
C50.0401 (17)0.0335 (16)0.0250 (15)0.0161 (14)0.0110 (13)0.0091 (12)
C20A0.0211 (13)0.0165 (12)0.0266 (14)0.0048 (10)0.0030 (11)0.0084 (11)
C60.0301 (15)0.0207 (13)0.0232 (14)0.0075 (11)0.0056 (11)0.0063 (11)
C70.0319 (15)0.0221 (13)0.0203 (14)0.0049 (12)0.0068 (11)0.0060 (11)
C19A0.0203 (13)0.0210 (13)0.0200 (13)0.0019 (11)0.0023 (10)0.0086 (10)
C18A0.0242 (14)0.0213 (13)0.0185 (13)0.0056 (11)0.0059 (10)0.0055 (10)
C80.0256 (14)0.0208 (13)0.0224 (14)0.0046 (11)0.0050 (11)0.0014 (11)
C17A0.0365 (17)0.0397 (17)0.0225 (15)0.0173 (14)0.0087 (12)0.0107 (13)
C90.0314 (16)0.0261 (14)0.0238 (14)0.0067 (12)0.0094 (12)0.0026 (11)
C16A0.0474 (19)0.0491 (19)0.0236 (15)0.0240 (16)0.0143 (14)0.0062 (14)
C100.0317 (16)0.0328 (16)0.0325 (16)0.0114 (13)0.0125 (13)0.0018 (13)
C110.0281 (15)0.0285 (15)0.0339 (16)0.0114 (12)0.0040 (12)0.0022 (12)
C15A0.0342 (16)0.0380 (17)0.0287 (16)0.0192 (14)0.0121 (13)0.0024 (13)
C14A0.0200 (13)0.0227 (13)0.0239 (14)0.0053 (11)0.0043 (11)0.0035 (11)
C120.0283 (15)0.0221 (13)0.0235 (14)0.0055 (12)0.0030 (11)0.0023 (11)
C13A0.0162 (12)0.0159 (12)0.0200 (13)0.0011 (10)0.0047 (10)0.0026 (10)
C130.0228 (14)0.0187 (13)0.0220 (14)0.0033 (11)0.0050 (11)0.0008 (10)
C140.0231 (14)0.0173 (12)0.0203 (13)0.0017 (11)0.0026 (10)0.0024 (10)
C12A0.0189 (13)0.0167 (12)0.0206 (13)0.0014 (10)0.0034 (10)0.0018 (10)
C11A0.0236 (14)0.0193 (13)0.0232 (14)0.0059 (11)0.0040 (11)0.0036 (11)
C150.0252 (14)0.0177 (12)0.0196 (13)0.0035 (11)0.0021 (11)0.0000 (10)
C10A0.0394 (18)0.0361 (17)0.0220 (15)0.0144 (14)0.0055 (13)0.0032 (12)
C160.0302 (15)0.0302 (15)0.0192 (14)0.0085 (12)0.0047 (11)0.0008 (11)
C9A0.063 (2)0.0401 (18)0.0267 (16)0.0267 (17)0.0068 (15)0.0143 (14)
C170.0367 (17)0.0340 (16)0.0249 (15)0.0166 (13)0.0075 (12)0.0011 (12)
C8A0.051 (2)0.0291 (16)0.0327 (17)0.0210 (15)0.0010 (14)0.0082 (13)
C180.0316 (16)0.0280 (14)0.0250 (15)0.0136 (12)0.0027 (12)0.0006 (12)
C7A0.0295 (15)0.0187 (13)0.0252 (14)0.0080 (11)0.0021 (11)0.0012 (11)
C190.0227 (14)0.0188 (13)0.0224 (14)0.0042 (11)0.0016 (11)0.0005 (10)
C6A0.0268 (14)0.0149 (12)0.0271 (15)0.0066 (11)0.0041 (11)0.0029 (11)
C200.0231 (14)0.0186 (13)0.0260 (14)0.0041 (11)0.0022 (11)0.0009 (11)
C0210.0285 (15)0.0305 (15)0.0244 (15)0.0102 (12)0.0033 (11)0.0082 (12)
C210.0372 (18)0.0424 (18)0.0384 (18)0.0217 (15)0.0055 (14)0.0159 (15)
C220.0419 (18)0.0403 (17)0.0208 (14)0.0205 (15)0.0063 (13)0.0084 (13)
C0220.0359 (17)0.0281 (15)0.0387 (17)0.0190 (13)0.0145 (13)0.0076 (13)
N010.0203 (11)0.0157 (10)0.0215 (11)0.0047 (9)0.0038 (9)0.0078 (9)
N020.0206 (11)0.0158 (10)0.0219 (11)0.0055 (9)0.0037 (9)0.0055 (9)
N030.0255 (12)0.0188 (11)0.0177 (11)0.0036 (9)0.0033 (9)0.0038 (9)
N040.0294 (13)0.0185 (11)0.0226 (12)0.0069 (10)0.0065 (10)0.0045 (9)
N070.0304 (13)0.0187 (12)0.0391 (14)0.0074 (10)0.0150 (11)0.0034 (10)
N080.0384 (15)0.0236 (12)0.0237 (12)0.0130 (11)0.0049 (10)0.0067 (10)
O10.0237 (9)0.0173 (9)0.0188 (9)0.0069 (7)0.0034 (7)0.0028 (7)
O1A0.0380 (16)0.099 (3)0.084 (2)0.0208 (16)0.0100 (15)0.024 (2)
O20.0246 (10)0.0196 (9)0.0167 (9)0.0086 (8)0.0054 (7)0.0059 (7)
O30.0308 (11)0.0233 (9)0.0254 (10)0.0155 (8)0.0068 (8)0.0058 (8)
O40.0267 (10)0.0231 (9)0.0206 (10)0.0103 (8)0.0013 (8)0.0059 (7)
O50.0206 (10)0.0169 (9)0.0363 (11)0.0057 (8)0.0033 (8)0.0077 (8)
O60.0209 (9)0.0172 (9)0.0189 (10)0.0052 (7)0.0030 (7)0.0040 (8)
O70.0310 (10)0.0226 (9)0.0201 (10)0.0097 (8)0.0082 (8)0.0055 (7)
O80.0340 (11)0.0217 (9)0.0194 (9)0.0107 (8)0.0078 (8)0.0024 (7)
O90.0349 (11)0.0256 (10)0.0179 (9)0.0131 (9)0.0043 (8)0.0037 (8)
O100.0362 (11)0.0295 (10)0.0247 (10)0.0154 (9)0.0061 (8)0.0084 (8)
O110.0342 (13)0.0217 (11)0.0334 (12)0.0043 (10)0.0028 (9)0.0033 (9)
O120.0319 (11)0.0190 (10)0.0229 (10)0.0078 (8)0.0066 (9)0.0017 (8)
O130.0346 (11)0.0331 (10)0.0604 (15)0.0043 (9)0.0002 (10)0.0015 (10)
O140.0487 (14)0.0199 (10)0.0402 (13)0.0102 (9)0.0085 (10)0.0024 (9)
O150.0620 (14)0.0528 (13)0.0459 (13)0.0404 (11)0.0113 (11)0.0024 (10)
O160.0244 (11)0.0204 (10)0.0500 (13)0.0040 (8)0.0126 (9)0.0052 (9)
O180.0480 (14)0.0181 (10)0.0614 (15)0.0122 (10)0.0224 (11)0.0103 (10)
Al10.0185 (4)0.0146 (4)0.0191 (4)0.0051 (3)0.0031 (3)0.0054 (3)
Al20.0274 (4)0.0183 (4)0.0188 (4)0.0069 (3)0.0051 (3)0.0040 (3)
C4R0.052 (2)0.065 (3)0.045 (2)0.006 (2)0.0040 (18)0.0008 (19)
O4T0.0620 (14)0.0528 (13)0.0459 (13)0.0404 (11)0.0113 (11)0.0024 (10)
C4T0.0620 (14)0.0528 (13)0.0459 (13)0.0404 (11)0.0113 (11)0.0024 (10)
O4U0.0346 (11)0.0331 (10)0.0604 (15)0.0043 (9)0.0002 (10)0.0015 (10)
C4U0.0346 (11)0.0331 (10)0.0604 (15)0.0043 (9)0.0002 (10)0.0015 (10)
O170.0264 (12)0.0281 (11)0.0793 (18)0.0105 (9)0.0118 (11)0.0024 (11)
Geometric parameters (Å, º) top
C1—C21.396 (4)C16—H160.9300
C1—C61.405 (4)C9A—C8A1.367 (4)
C1—N031.419 (3)C9A—H9A0.9300
C5A—C4A1.385 (4)C17—C181.370 (4)
C5A—C20A1.398 (4)C17—H170.9300
C5A—N021.426 (3)C8A—C7A1.415 (4)
C1T—O1A1.293 (6)C8A—H8A0.9300
C1T—C2T1.517 (6)C18—C191.409 (4)
C1T—H1T10.9700C18—H180.9300
C1T—H1T20.9700C7A—C6A1.441 (4)
C4A—C3A1.381 (4)C19—C201.435 (4)
C4A—H4A0.9300C6A—N021.294 (3)
C2—C31.382 (4)C6A—H6A0.9300
C2—H20.9300C20—N031.303 (4)
C2T—H2TA0.9600C20—H200.9300
C2T—H2TB0.9600C021—O41.431 (3)
C2T—H2TC0.9600C021—H02A0.9600
C3—C41.390 (4)C021—H02B0.9600
C3—H30.9300C021—H02C0.9600
C3A—C2A1.384 (5)C21—O101.436 (3)
C3A—H3A0.9300C21—H21A0.9600
C4—C51.383 (4)C21—H21B0.9600
C4—H40.9300C21—H21C0.9600
C2A—C1A1.379 (4)C22—O91.431 (3)
C2A—H2A0.9300C22—H22A0.9600
C1A—C20A1.399 (4)C22—H22B0.9600
C1A—H1A0.9300C22—H22C0.9600
C5—C61.390 (4)C022—O31.425 (3)
C5—H50.9300C022—H02D0.9600
C20A—N011.420 (3)C022—H02E0.9600
C6—N041.423 (3)C022—H02F0.9600
C7—N041.301 (4)N01—Al12.007 (2)
C7—C81.430 (4)N02—Al11.988 (2)
C7—H70.9300N03—Al21.991 (2)
C19A—N011.296 (3)N04—Al21.998 (2)
C19A—C18A1.442 (4)N07—O181.229 (3)
C19A—H19A0.9300N07—O171.252 (3)
C18A—C13A1.406 (4)N07—O161.263 (3)
C18A—C17A1.417 (4)N08—O131.233 (3)
C8—C131.405 (4)N08—O141.235 (3)
C8—C91.418 (4)N08—O151.261 (3)
C17A—C16A1.354 (4)O1—Al11.8197 (19)
C17A—H17A0.9300O1A—H1AA0.8200
C9—C101.360 (4)O2—Al11.8066 (19)
C9—H90.9300O5—Al11.918 (2)
C16A—C15A1.403 (4)O5—H520.870 (18)
C16A—H16A0.9300O5—H510.845 (19)
C10—C111.406 (4)O6—Al11.958 (2)
C10—H100.9300O6—H610.871 (18)
C11—C121.376 (4)O6—H620.860 (18)
C11—H110.9300O7—Al21.812 (2)
C15A—C14A1.376 (4)O8—Al21.809 (2)
C15A—H15A0.9300O11—Al21.925 (2)
C14A—O31.376 (3)O11—H11B0.852 (19)
C14A—C13A1.413 (4)O11—H11A0.826 (19)
C12—O101.376 (3)O12—Al21.977 (2)
C12—C131.411 (4)O12—H12B0.852 (18)
C13A—O21.324 (3)O12—H12A0.848 (19)
C13—O71.330 (3)C4R—C4T1.340 (7)
C14—O81.316 (3)C4R—C4U1.504 (9)
C14—C191.415 (4)C4R—H4R10.9600
C14—C151.421 (4)C4R—H4R20.9600
C12A—O11.321 (3)C4R—H4R30.9600
C12A—C7A1.410 (4)O4T—C4T1.410 (4)
C12A—C11A1.417 (4)O4T—H4T0.8200
C11A—O41.375 (3)C4T—H4T10.9700
C11A—C10A1.378 (4)C4T—H4T20.9700
C15—O91.372 (3)O4U—C4U1.376 (9)
C15—C161.372 (4)O4U—H4U1.2082
C10A—C9A1.400 (4)C4U—H4U10.9700
C10A—H10A0.9300C4U—H4U20.9700
C16—C171.404 (4)
C2—C1—C6119.3 (2)C18—C19—C14119.5 (2)
C2—C1—N03125.6 (3)C18—C19—C20117.7 (2)
C6—C1—N03115.1 (2)C14—C19—C20122.8 (2)
C4A—C5A—C20A120.2 (2)N02—C6A—C7A124.5 (2)
C4A—C5A—N02124.6 (3)N02—C6A—H6A117.8
C20A—C5A—N02115.1 (2)C7A—C6A—H6A117.8
O1A—C1T—C2T113.9 (4)N03—C20—C19124.8 (3)
O1A—C1T—H1T1108.8N03—C20—H20117.6
C2T—C1T—H1T1108.8C19—C20—H20117.6
O1A—C1T—H1T2108.8O4—C021—H02A109.5
C2T—C1T—H1T2108.8O4—C021—H02B109.5
H1T1—C1T—H1T2107.7H02A—C021—H02B109.5
C3A—C4A—C5A119.9 (3)O4—C021—H02C109.5
C3A—C4A—H4A120.0H02A—C021—H02C109.5
C5A—C4A—H4A120.0H02B—C021—H02C109.5
C3—C2—C1119.9 (3)O10—C21—H21A109.5
C3—C2—H2120.0O10—C21—H21B109.5
C1—C2—H2120.0H21A—C21—H21B109.5
C1T—C2T—H2TA109.5O10—C21—H21C109.5
C1T—C2T—H2TB109.5H21A—C21—H21C109.5
H2TA—C2T—H2TB109.5H21B—C21—H21C109.5
C1T—C2T—H2TC109.5O9—C22—H22A109.5
H2TA—C2T—H2TC109.5O9—C22—H22B109.5
H2TB—C2T—H2TC109.5H22A—C22—H22B109.5
C2—C3—C4120.6 (3)O9—C22—H22C109.5
C2—C3—H3119.7H22A—C22—H22C109.5
C4—C3—H3119.7H22B—C22—H22C109.5
C4A—C3A—C2A120.0 (3)O3—C022—H02D109.5
C4A—C3A—H3A120.0O3—C022—H02E109.5
C2A—C3A—H3A120.0H02D—C022—H02E109.5
C5—C4—C3120.0 (3)O3—C022—H02F109.5
C5—C4—H4120.0H02D—C022—H02F109.5
C3—C4—H4120.0H02E—C022—H02F109.5
C1A—C2A—C3A121.0 (3)C19A—N01—C20A122.2 (2)
C1A—C2A—H2A119.5C19A—N01—Al1124.05 (18)
C3A—C2A—H2A119.5C20A—N01—Al1113.73 (17)
C2A—C1A—C20A119.3 (3)C6A—N02—C5A121.5 (2)
C2A—C1A—H1A120.3C6A—N02—Al1124.28 (18)
C20A—C1A—H1A120.3C5A—N02—Al1113.89 (17)
C4—C5—C6120.0 (3)C20—N03—C1121.2 (2)
C4—C5—H5120.0C20—N03—Al2124.53 (19)
C6—C5—H5120.0C1—N03—Al2114.18 (18)
C5A—C20A—C1A119.5 (3)C7—N04—C6121.2 (2)
C5A—C20A—N01114.8 (2)C7—N04—Al2124.68 (19)
C1A—C20A—N01125.7 (3)C6—N04—Al2113.82 (18)
C5—C6—C1120.0 (3)O18—N07—O17120.7 (2)
C5—C6—N04125.0 (3)O18—N07—O16120.7 (2)
C1—C6—N04115.0 (2)O17—N07—O16118.6 (2)
N04—C7—C8125.1 (2)O13—N08—O14121.5 (3)
N04—C7—H7117.4O13—N08—O15118.1 (3)
C8—C7—H7117.4O14—N08—O15120.4 (3)
N01—C19A—C18A124.6 (2)C12A—O1—Al1128.82 (16)
N01—C19A—H19A117.7C1T—O1A—H1AA109.5
C18A—C19A—H19A117.7C13A—O2—Al1129.86 (16)
C13A—C18A—C17A119.5 (3)C14A—O3—C022117.7 (2)
C13A—C18A—C19A123.0 (2)C11A—O4—C021116.4 (2)
C17A—C18A—C19A117.4 (2)Al1—O5—H52121 (2)
C13—C8—C9119.2 (3)Al1—O5—H51126 (3)
C13—C8—C7122.7 (3)H52—O5—H51109 (4)
C9—C8—C7118.0 (2)Al1—O6—H61110 (3)
C16A—C17A—C18A120.8 (3)Al1—O6—H62111 (2)
C16A—C17A—H17A119.6H61—O6—H62108 (3)
C18A—C17A—H17A119.6C13—O7—Al2130.62 (17)
C10—C9—C8121.2 (3)C14—O8—Al2130.45 (17)
C10—C9—H9119.4C15—O9—C22117.1 (2)
C8—C9—H9119.4C12—O10—C21117.0 (2)
C17A—C16A—C15A120.3 (3)Al2—O11—H11B124 (3)
C17A—C16A—H16A119.9Al2—O11—H11A125 (3)
C15A—C16A—H16A119.9H11B—O11—H11A111 (4)
C9—C10—C11119.7 (3)Al2—O12—H12B112 (2)
C9—C10—H10120.2Al2—O12—H12A116 (3)
C11—C10—H10120.2H12B—O12—H12A106 (4)
C12—C11—C10120.3 (3)O2—Al1—O193.64 (8)
C12—C11—H11119.8O2—Al1—O591.91 (9)
C10—C11—H11119.8O1—Al1—O593.74 (9)
C14A—C15A—C16A120.2 (3)O2—Al1—O690.49 (9)
C14A—C15A—H15A119.9O1—Al1—O690.72 (8)
C16A—C15A—H15A119.9O5—Al1—O6174.80 (9)
O3—C14A—C15A125.2 (3)O2—Al1—N02174.22 (9)
O3—C14A—C13A114.0 (2)O1—Al1—N0292.09 (9)
C15A—C14A—C13A120.7 (2)O5—Al1—N0288.49 (10)
C11—C12—O10125.3 (3)O6—Al1—N0288.67 (9)
C11—C12—C13120.9 (3)O2—Al1—N0193.08 (9)
O10—C12—C13113.8 (2)O1—Al1—N01172.56 (10)
O2—C13A—C18A124.0 (2)O5—Al1—N0189.23 (9)
O2—C13A—C14A117.5 (2)O6—Al1—N0186.03 (8)
C18A—C13A—C14A118.4 (2)N02—Al1—N0181.16 (9)
O7—C13—C8123.8 (2)O8—Al2—O792.64 (9)
O7—C13—C12117.5 (2)O8—Al2—O1193.25 (9)
C8—C13—C12118.6 (2)O7—Al2—O1190.98 (10)
O8—C14—C19123.9 (2)O8—Al2—O1290.12 (9)
O8—C14—C15118.0 (2)O7—Al2—O1292.38 (9)
C19—C14—C15118.2 (2)O11—Al2—O12175.12 (10)
O1—C12A—C7A123.9 (2)O8—Al2—N0393.18 (9)
O1—C12A—C11A118.2 (2)O7—Al2—N03173.99 (9)
C7A—C12A—C11A117.9 (2)O11—Al2—N0387.18 (10)
O4—C11A—C10A125.1 (2)O12—Al2—N0389.12 (10)
O4—C11A—C12A113.7 (2)O8—Al2—N04173.64 (10)
C10A—C11A—C12A121.2 (3)O7—Al2—N0492.57 (9)
O9—C15—C16125.2 (2)O11—Al2—N0490.32 (10)
O9—C15—C14113.5 (2)O12—Al2—N0486.01 (9)
C16—C15—C14121.2 (3)N03—Al2—N0481.73 (9)
C11A—C10A—C9A119.8 (3)C4T—C4R—H4R1109.5
C11A—C10A—H10A120.1C4T—C4R—H4R2109.5
C9A—C10A—H10A120.1H4R1—C4R—H4R2109.5
C15—C16—C17119.9 (3)C4T—C4R—H4R3109.5
C15—C16—H16120.0H4R1—C4R—H4R3109.5
C17—C16—H16120.0H4R2—C4R—H4R3109.5
C8A—C9A—C10A120.6 (3)C4T—O4T—H4T109.5
C8A—C9A—H9A119.7C4R—C4T—O4T112.5 (6)
C10A—C9A—H9A119.7C4R—C4T—H4T1109.1
C18—C17—C16120.3 (3)O4T—C4T—H4T1109.1
C18—C17—H17119.8C4R—C4T—H4T2109.1
C16—C17—H17119.8O4T—C4T—H4T2109.1
C9A—C8A—C7A120.2 (3)H4T1—C4T—H4T2107.8
C9A—C8A—H8A119.9C4U—O4U—H4U104.5
C7A—C8A—H8A119.9O4U—C4U—C4R117.6 (7)
C17—C18—C19120.9 (3)O4U—C4U—H4U1107.9
C17—C18—H18119.6C4R—C4U—H4U1107.9
C19—C18—H18119.6O4U—C4U—H4U2107.9
C12A—C7A—C8A120.0 (2)C4R—C4U—H4U2107.9
C12A—C7A—C6A122.3 (2)H4U1—C4U—H4U2107.2
C8A—C7A—C6A117.7 (3)
C20A—C5A—C4A—C3A1.1 (4)O1—C12A—C7A—C6A4.1 (4)
N02—C5A—C4A—C3A179.3 (3)C11A—C12A—C7A—C6A174.5 (2)
C6—C1—C2—C32.3 (4)C9A—C8A—C7A—C12A0.5 (5)
N03—C1—C2—C3177.5 (3)C9A—C8A—C7A—C6A178.9 (3)
C1—C2—C3—C40.9 (5)C17—C18—C19—C140.3 (4)
C5A—C4A—C3A—C2A0.2 (4)C17—C18—C19—C20178.5 (3)
C2—C3—C4—C51.8 (5)O8—C14—C19—C18179.4 (2)
C4A—C3A—C2A—C1A0.9 (5)C15—C14—C19—C180.6 (4)
C3A—C2A—C1A—C20A1.0 (4)O8—C14—C19—C201.3 (4)
C3—C4—C5—C60.4 (5)C15—C14—C19—C20178.7 (2)
C4A—C5A—C20A—C1A1.0 (4)C12A—C7A—C6A—N024.8 (4)
N02—C5A—C20A—C1A179.3 (2)C8A—C7A—C6A—N02176.9 (3)
C4A—C5A—C20A—N01177.2 (2)C18—C19—C20—N03178.8 (3)
N02—C5A—C20A—N011.1 (3)C14—C19—C20—N030.6 (4)
C2A—C1A—C20A—C5A0.0 (4)C18A—C19A—N01—C20A175.4 (2)
C2A—C1A—C20A—N01178.1 (2)C18A—C19A—N01—Al16.1 (3)
C4—C5—C6—C13.6 (4)C5A—C20A—N01—C19A171.3 (2)
C4—C5—C6—N04176.5 (3)C1A—C20A—N01—C19A10.6 (4)
C2—C1—C6—C54.5 (4)C5A—C20A—N01—Al17.3 (3)
N03—C1—C6—C5175.3 (2)C1A—C20A—N01—Al1170.8 (2)
C2—C1—C6—N04175.6 (2)C7A—C6A—N02—C5A176.4 (2)
N03—C1—C6—N044.6 (3)C7A—C6A—N02—Al110.2 (4)
N01—C19A—C18A—C13A4.1 (4)C4A—C5A—N02—C6A16.8 (4)
N01—C19A—C18A—C17A179.3 (3)C20A—C5A—N02—C6A164.9 (2)
N04—C7—C8—C131.6 (4)C4A—C5A—N02—Al1169.2 (2)
N04—C7—C8—C9177.5 (3)C20A—C5A—N02—Al19.1 (3)
C13A—C18A—C17A—C16A0.4 (4)C19—C20—N03—C1178.6 (2)
C19A—C18A—C17A—C16A176.2 (3)C19—C20—N03—Al24.2 (4)
C13—C8—C9—C100.3 (4)C2—C1—N03—C200.2 (4)
C7—C8—C9—C10179.4 (3)C6—C1—N03—C20180.0 (2)
C18A—C17A—C16A—C15A1.8 (5)C2—C1—N03—Al2177.7 (2)
C8—C9—C10—C110.4 (4)C6—C1—N03—Al22.6 (3)
C9—C10—C11—C120.1 (4)C8—C7—N04—C6179.3 (2)
C17A—C16A—C15A—C14A1.2 (5)C8—C7—N04—Al26.4 (4)
C16A—C15A—C14A—O3179.2 (3)C5—C6—N04—C711.0 (4)
C16A—C15A—C14A—C13A1.8 (4)C1—C6—N04—C7169.1 (2)
C10—C11—C12—O10179.2 (3)C5—C6—N04—Al2175.4 (2)
C10—C11—C12—C130.9 (4)C1—C6—N04—Al24.5 (3)
C17A—C18A—C13A—O2177.9 (2)C7A—C12A—O1—Al113.5 (4)
C19A—C18A—C13A—O25.7 (4)C11A—C12A—O1—Al1167.85 (18)
C17A—C18A—C13A—C14A3.3 (4)C18A—C13A—O2—Al14.5 (3)
C19A—C18A—C13A—C14A173.2 (2)C14A—C13A—O2—Al1176.65 (17)
O3—C14A—C13A—O22.1 (3)C15A—C14A—O3—C0222.1 (4)
C15A—C14A—C13A—O2177.1 (2)C13A—C14A—O3—C022178.7 (2)
O3—C14A—C13A—C18A176.9 (2)C10A—C11A—O4—C0217.1 (4)
C15A—C14A—C13A—C18A3.9 (4)C12A—C11A—O4—C021174.5 (2)
C9—C8—C13—O7179.7 (2)C8—C13—O7—Al22.8 (4)
C7—C8—C13—O70.7 (4)C12—C13—O7—Al2177.91 (18)
C9—C8—C13—C120.5 (4)C19—C14—O8—Al23.6 (4)
C7—C8—C13—C12178.6 (2)C15—C14—O8—Al2176.38 (17)
C11—C12—C13—O7179.6 (2)C16—C15—O9—C2213.3 (4)
O10—C12—C13—O70.3 (3)C14—C15—O9—C22167.7 (2)
C11—C12—C13—C81.1 (4)C11—C12—O10—C210.1 (4)
O10—C12—C13—C8179.0 (2)C13—C12—O10—C21180.0 (2)
O1—C12A—C11A—O42.5 (3)C13A—O2—Al1—O1172.4 (2)
C7A—C12A—C11A—O4176.2 (2)C13A—O2—Al1—O578.5 (2)
O1—C12A—C11A—C10A176.0 (2)C13A—O2—Al1—O696.9 (2)
C7A—C12A—C11A—C10A5.3 (4)C13A—O2—Al1—N0110.8 (2)
O8—C14—C15—O90.3 (3)C12A—O1—Al1—O2159.5 (2)
C19—C14—C15—O9179.7 (2)C12A—O1—Al1—O567.4 (2)
O8—C14—C15—C16179.3 (2)C12A—O1—Al1—O6109.9 (2)
C19—C14—C15—C160.6 (4)C12A—O1—Al1—N0221.2 (2)
O4—C11A—C10A—C9A179.2 (3)C14—O8—Al2—O7172.2 (2)
C12A—C11A—C10A—C9A2.4 (5)C14—O8—Al2—O1181.1 (2)
O9—C15—C16—C17179.3 (2)C14—O8—Al2—O1295.4 (2)
C14—C15—C16—C170.4 (4)C14—O8—Al2—N036.3 (2)
C11A—C10A—C9A—C8A2.1 (5)C13—O7—Al2—O8178.1 (2)
C15—C16—C17—C180.1 (4)C13—O7—Al2—O1184.8 (2)
C10A—C9A—C8A—C7A3.5 (5)C13—O7—Al2—O1291.7 (2)
C16—C17—C18—C190.1 (4)C13—O7—Al2—N045.6 (2)
O1—C12A—C7A—C8A177.5 (3)C4U—C4R—C4T—O4T171 (6)
C11A—C12A—C7A—C8A3.8 (4)C4T—C4R—C4U—O4U7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H52···O160.87 (2)1.83 (3)2.684 (3)169 (3)
O11—H11B···O1A0.85 (3)1.73 (3)2.573 (4)178 (7)
Diaqua(6,6'-{(1E,1'E)-[1,2-phenylenebis(azanylylidene)]bis(methanylylidene)}bis(2-methoxyphenolato)-κ4O1,N,N',O1')gallium(III) nitrate ethanol monosolvate (16rjt1_0m) top
Crystal data top
[Ga(C22H18N2O4)(H2O)2]NO3·C2H6OZ = 4
Mr = 588.21F(000) = 1216
Triclinic, P1Dx = 1.576 Mg m3
a = 12.399 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.580 (5) ÅCell parameters from 11972 reflections
c = 16.419 (5) Åθ = 1.0–1.0°
α = 86.818 (5)°µ = 1.17 mm1
β = 78.871 (5)°T = 100 K
γ = 66.124 (5)°Cuboid, yellow
V = 2479.7 (16) Å30.57 × 0.24 × 0.23 mm
Data collection top
Bruker APEXII CCD
diffractometer
Rint = 0.027
φ and ω scansθmax = 28.0°, θmin = 1.6°
47407 measured reflectionsh = 1616
11972 independent reflectionsk = 1617
10426 reflections with I > 2σ(I)l = 2120
Refinement top
Refinement on F220 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0422P)2 + 5.8146P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.002
11886 reflectionsΔρmax = 1.84 e Å3
682 parametersΔρmin = 2.07 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ga010.45155 (2)0.17569 (2)0.95269 (2)0.01661 (6)
Ga020.08156 (2)0.32174 (2)0.54724 (2)0.01661 (6)
O60.29643 (18)0.05042 (15)0.90092 (12)0.0244 (4)
N2A0.0987 (2)0.28745 (17)0.66651 (13)0.0206 (4)
C7A0.0959 (3)0.2234 (2)0.29245 (18)0.0292 (5)
H7A0.12860.19510.25840.035*
O40.39050 (16)0.08262 (14)0.91687 (10)0.0185 (3)
C15A0.2812 (2)0.4138 (2)0.72964 (17)0.0247 (5)
H15A0.28120.38580.78260.030*
C12A0.2796 (2)0.4998 (2)0.57193 (16)0.0224 (5)
O30.40813 (16)0.14689 (14)1.06566 (10)0.0187 (3)
O50.31225 (16)0.09519 (14)1.20518 (11)0.0213 (4)
C40.4966 (2)0.3212 (2)1.05411 (17)0.0225 (5)
H40.52270.37551.05930.027*
C210.2664 (3)0.0603 (2)1.28266 (17)0.0263 (6)
H21A0.25090.00151.27340.039*
H21B0.19320.11741.30840.039*
H21C0.32430.04171.31840.039*
C180.5848 (2)0.26915 (19)0.83385 (16)0.0199 (5)
O250.2711 (2)0.53867 (18)0.49337 (14)0.0349 (3)
O6A0.04001 (17)0.42112 (15)0.28984 (11)0.0231 (4)
O10.61681 (16)0.04865 (14)0.94634 (11)0.0188 (3)
C170.4886 (2)0.1814 (2)0.77038 (15)0.0210 (5)
H170.51520.20610.71980.025*
O160.32134 (19)0.49178 (16)0.92363 (15)0.0351 (5)
C220.2458 (3)0.1268 (2)0.8949 (2)0.0314 (6)
H22A0.22770.15310.94900.047*
H22B0.30230.18580.85880.047*
H22C0.17350.09270.87280.047*
O2A0.08101 (17)0.44875 (14)0.59385 (11)0.0209 (4)
C2A0.0556 (3)0.1040 (2)0.67441 (18)0.0274 (6)
H2AC0.08520.07550.63810.033*
O5A0.16622 (17)0.41135 (14)0.53847 (11)0.0216 (4)
C150.4045 (3)0.0944 (2)0.69046 (17)0.0293 (6)
H150.43090.12620.64370.035*
O4A0.04988 (17)0.35558 (14)0.43888 (11)0.0208 (4)
O100.3168 (2)0.84316 (16)0.42534 (14)0.0324 (4)
C22A0.3271 (3)0.6109 (3)0.4661 (2)0.0349 (3)
H22D0.31540.63270.41070.052*
H22E0.41150.57560.46660.052*
H22F0.29210.67320.50260.052*
C11A0.2196 (2)0.42986 (19)0.59469 (16)0.0198 (5)
O20.29328 (17)0.30294 (15)0.95132 (13)0.0265 (4)
O110.3445 (2)0.9705 (2)0.48120 (15)0.0409 (5)
C3A0.0052 (2)0.1777 (2)0.64648 (16)0.0217 (5)
O120.1678 (2)0.99308 (18)0.46706 (17)0.0440 (6)
C160.4232 (2)0.1152 (2)0.76905 (15)0.0210 (5)
C5A0.0401 (2)0.2303 (2)0.42517 (15)0.0196 (5)
C16A0.2210 (2)0.3868 (2)0.67492 (16)0.0214 (5)
O70.1295 (2)0.54519 (18)0.93591 (18)0.0443 (6)
C6A0.0894 (2)0.1882 (2)0.37179 (17)0.0245 (5)
H6A0.11780.13580.39100.029*
N10.52160 (19)0.27638 (16)0.98134 (13)0.0180 (4)
C140.3483 (3)0.0283 (3)0.68225 (18)0.0339 (7)
H140.33520.01680.63040.041*
C110.3817 (2)0.06723 (19)0.84022 (15)0.0181 (5)
N1A0.00006 (19)0.21935 (16)0.56512 (13)0.0197 (4)
N30.2764 (2)0.93433 (18)0.45785 (13)0.0235 (5)
C21A0.0575 (3)0.4449 (2)0.20350 (16)0.0287 (6)
H21D0.08850.49970.19530.043*
H21E0.01780.46990.18490.043*
H21F0.11350.38100.17230.043*
N40.2209 (2)0.56655 (18)0.92205 (16)0.0278 (5)
O90.2115 (2)0.65943 (17)0.90632 (17)0.0430 (6)
C4A0.0400 (2)0.1895 (2)0.50775 (16)0.0217 (5)
H4A0.07110.13760.52120.026*
N20.51356 (18)0.20938 (16)0.83601 (13)0.0177 (4)
C10A0.0034 (2)0.30990 (19)0.39546 (15)0.0181 (5)
C190.6505 (3)0.2923 (2)0.76180 (18)0.0270 (6)
H190.64800.26930.71010.032*
C18A0.0431 (2)0.2177 (2)0.70141 (16)0.0219 (5)
C120.3280 (2)0.0041 (2)0.82891 (16)0.0210 (5)
C130.3104 (3)0.0219 (2)0.75171 (18)0.0292 (6)
H130.27320.06760.74570.035*
C80.3146 (3)0.2457 (2)1.27768 (17)0.0310 (6)
H80.27640.22981.32800.037*
C100.3942 (2)0.20751 (19)1.12989 (15)0.0181 (5)
C50.4317 (2)0.2934 (2)1.12719 (16)0.0230 (5)
C90.3389 (2)0.1830 (2)1.20792 (16)0.0206 (5)
C8A0.0531 (2)0.3023 (2)0.26230 (16)0.0246 (5)
H8A0.05790.32630.20840.030*
C19A0.0328 (3)0.1886 (2)0.78431 (17)0.0280 (6)
H19A0.06090.21750.82150.034*
C1A0.0613 (3)0.0734 (2)0.75655 (19)0.0317 (6)
H1AA0.09360.02340.77500.038*
C9A0.0041 (2)0.3440 (2)0.31235 (15)0.0196 (5)
C17A0.1613 (2)0.3171 (2)0.70624 (16)0.0222 (5)
H17A0.16830.29140.75950.027*
C13A0.3384 (2)0.5236 (2)0.62578 (18)0.0264 (6)
H13A0.37810.56870.60930.032*
C14A0.3390 (3)0.4803 (2)0.70562 (18)0.0280 (6)
H14A0.37860.49690.74190.034*
C20A0.0192 (3)0.1167 (2)0.81145 (18)0.0315 (6)
H20A0.02590.09730.86680.038*
C30.5900 (2)0.30404 (19)0.91141 (16)0.0203 (5)
C20.6618 (3)0.3594 (2)0.91662 (19)0.0285 (6)
H20.66660.38100.96810.034*
C200.7193 (3)0.3496 (2)0.7677 (2)0.0325 (6)
H200.76150.36660.71970.039*
C10.7257 (3)0.3818 (3)0.8447 (2)0.0341 (7)
H10.77360.41880.84800.041*
C60.4077 (3)0.3553 (2)1.2003 (2)0.0354 (7)
H60.43330.41111.19880.042*
C70.3474 (3)0.3337 (3)1.2728 (2)0.0417 (8)
H70.32780.37761.31950.050*
C6B0.5687 (4)0.2399 (3)0.3791 (3)0.0535 (9)
H6BA0.58480.30000.35560.080*
H6BB0.54050.21100.33960.080*
H6BC0.64100.18530.39250.080*
C5B0.4736 (3)0.2769 (3)0.4573 (2)0.0349 (3)
H5BA0.50190.30740.49640.042*
H5BB0.40140.33320.44360.042*
C2B0.0900 (6)0.1407 (6)0.0735 (4)0.0292 (5)0.492 (6)
H2BA0.15680.13760.09660.044*0.492 (6)
H2BB0.10020.06890.06070.044*0.492 (6)
H2BC0.01700.17460.11300.044*0.492 (6)
O130.0912 (4)0.2902 (3)0.0223 (4)0.0324 (4)0.492 (6)
H13B0.10640.29090.06860.049*0.492 (6)
C4B0.0849 (8)0.1940 (6)0.0085 (5)0.0349 (3)0.492 (6)
H4BA0.01030.20760.00970.042*0.492 (6)
H4BB0.15080.15290.03510.042*0.492 (6)
C3B0.0713 (5)0.1925 (5)0.0128 (4)0.0217 (5)0.508 (6)
H3BA0.13630.14540.05420.026*0.508 (6)
H3BB0.00190.20480.03260.026*0.508 (6)
C1B0.0688 (9)0.1200 (7)0.0651 (6)0.0535 (9)0.508 (6)
H1BA0.06060.05660.04950.080*0.508 (6)
H1BB0.00200.15970.10770.080*0.508 (6)
H1BC0.14210.09940.08570.080*0.508 (6)
O150.0815 (5)0.2894 (4)0.0210 (4)0.0409 (5)0.508 (6)
H15B0.04100.32830.01970.061*0.508 (6)
O140.4471 (2)0.1992 (3)0.4926 (2)0.0653 (9)
H14B0.50910.14780.49850.098*
H1A0.614 (5)0.004 (3)0.922 (3)0.098*
H1B0.626 (5)0.033 (4)0.9960 (16)0.098*
H2A0.223 (3)0.304 (4)0.971 (4)0.098*
H2B0.289 (5)0.367 (2)0.952 (4)0.098*
H2AA0.070 (5)0.498 (3)0.613 (3)0.098*
H2AB0.122 (5)0.468 (4)0.556 (3)0.098*
O0AA0.23809 (18)0.19361 (15)0.50397 (13)0.0288 (4)
H0AA0.23780.13550.52780.043*
H0AB0.29740.20110.51880.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ga010.02039 (10)0.01428 (10)0.01347 (10)0.00593 (7)0.00250 (7)0.00317 (7)
Ga020.02039 (10)0.01428 (10)0.01347 (10)0.00593 (7)0.00250 (7)0.00317 (7)
O60.0307 (10)0.0245 (9)0.0236 (9)0.0170 (8)0.0055 (8)0.0036 (7)
N2A0.0242 (11)0.0177 (10)0.0166 (10)0.0055 (8)0.0040 (8)0.0040 (8)
C7A0.0301 (13)0.0338 (14)0.0239 (12)0.0119 (11)0.0061 (10)0.0046 (10)
O40.0250 (9)0.0179 (8)0.0142 (8)0.0104 (7)0.0046 (7)0.0041 (6)
C15A0.0257 (13)0.0247 (13)0.0198 (12)0.0056 (11)0.0060 (10)0.0026 (10)
C12A0.0210 (12)0.0186 (12)0.0214 (12)0.0032 (10)0.0002 (9)0.0007 (9)
O30.0258 (9)0.0160 (8)0.0140 (8)0.0096 (7)0.0004 (7)0.0015 (6)
O50.0249 (9)0.0218 (9)0.0151 (8)0.0098 (7)0.0012 (7)0.0035 (7)
C40.0256 (13)0.0138 (11)0.0274 (13)0.0075 (10)0.0044 (10)0.0012 (9)
C210.0255 (13)0.0271 (13)0.0198 (12)0.0080 (11)0.0033 (10)0.0065 (10)
C180.0194 (11)0.0144 (11)0.0225 (12)0.0052 (9)0.0012 (9)0.0068 (9)
O250.0359 (8)0.0359 (8)0.0299 (8)0.0133 (7)0.0031 (6)0.0044 (6)
O6A0.0306 (10)0.0239 (9)0.0153 (8)0.0117 (8)0.0042 (7)0.0029 (7)
O10.0202 (8)0.0159 (8)0.0170 (8)0.0049 (7)0.0022 (7)0.0030 (6)
C170.0214 (12)0.0198 (12)0.0155 (11)0.0036 (10)0.0013 (9)0.0065 (9)
O160.0285 (11)0.0205 (10)0.0529 (14)0.0028 (8)0.0160 (10)0.0012 (9)
C220.0360 (16)0.0267 (14)0.0392 (17)0.0183 (12)0.0135 (13)0.0051 (12)
O2A0.0253 (9)0.0169 (8)0.0174 (9)0.0055 (7)0.0034 (7)0.0006 (7)
C2A0.0365 (15)0.0216 (13)0.0245 (13)0.0122 (11)0.0072 (11)0.0051 (10)
O5A0.0266 (9)0.0206 (9)0.0166 (8)0.0081 (7)0.0058 (7)0.0038 (7)
C150.0347 (15)0.0346 (15)0.0170 (12)0.0117 (12)0.0079 (11)0.0058 (11)
O4A0.0291 (10)0.0182 (8)0.0145 (8)0.0087 (7)0.0048 (7)0.0012 (6)
O100.0352 (10)0.0208 (9)0.0377 (11)0.0085 (8)0.0035 (8)0.0055 (8)
C22A0.0359 (8)0.0359 (8)0.0299 (8)0.0133 (7)0.0031 (6)0.0044 (6)
C11A0.0184 (11)0.0165 (11)0.0191 (12)0.0025 (9)0.0010 (9)0.0001 (9)
O20.0202 (9)0.0159 (8)0.0388 (11)0.0048 (7)0.0026 (8)0.0068 (8)
O110.0513 (13)0.0439 (12)0.0392 (12)0.0288 (11)0.0124 (10)0.0003 (9)
C3A0.0250 (13)0.0161 (11)0.0186 (12)0.0043 (10)0.0018 (9)0.0038 (9)
O120.0339 (12)0.0271 (11)0.0552 (15)0.0013 (9)0.0029 (11)0.0004 (10)
C160.0222 (12)0.0196 (12)0.0163 (11)0.0032 (10)0.0048 (9)0.0037 (9)
C5A0.0174 (11)0.0174 (11)0.0184 (12)0.0024 (9)0.0002 (9)0.0011 (9)
C16A0.0211 (12)0.0187 (11)0.0203 (12)0.0039 (10)0.0040 (9)0.0025 (9)
O70.0298 (12)0.0285 (11)0.0762 (18)0.0123 (9)0.0111 (11)0.0031 (11)
C6A0.0239 (13)0.0249 (13)0.0239 (13)0.0100 (11)0.0012 (10)0.0018 (10)
N10.0192 (10)0.0142 (9)0.0199 (10)0.0068 (8)0.0031 (8)0.0042 (8)
C140.0410 (17)0.0439 (17)0.0203 (13)0.0174 (14)0.0131 (12)0.0019 (12)
C110.0176 (11)0.0162 (11)0.0166 (11)0.0025 (9)0.0047 (9)0.0020 (9)
N1A0.0219 (10)0.0153 (9)0.0168 (10)0.0036 (8)0.0012 (8)0.0019 (8)
N30.0350 (13)0.0196 (10)0.0160 (10)0.0122 (9)0.0036 (9)0.0042 (8)
C21A0.0353 (15)0.0369 (15)0.0167 (12)0.0184 (13)0.0041 (11)0.0060 (11)
N40.0312 (12)0.0172 (10)0.0353 (13)0.0069 (9)0.0136 (10)0.0012 (9)
O90.0496 (14)0.0171 (10)0.0662 (17)0.0134 (10)0.0217 (12)0.0076 (10)
C4A0.0210 (11)0.0203 (10)0.0191 (11)0.0044 (9)0.0017 (9)0.0001 (9)
N20.0176 (10)0.0151 (9)0.0172 (10)0.0049 (8)0.0011 (8)0.0054 (7)
C10A0.0168 (11)0.0154 (11)0.0160 (11)0.0010 (9)0.0006 (9)0.0023 (9)
C190.0273 (14)0.0251 (13)0.0239 (13)0.0098 (11)0.0025 (11)0.0062 (10)
C18A0.0245 (12)0.0177 (11)0.0196 (12)0.0054 (10)0.0032 (10)0.0049 (9)
C120.0202 (12)0.0202 (12)0.0207 (12)0.0057 (10)0.0050 (9)0.0023 (9)
C130.0301 (14)0.0345 (15)0.0272 (14)0.0150 (12)0.0098 (11)0.0012 (11)
C80.0369 (16)0.0331 (15)0.0179 (13)0.0128 (13)0.0054 (11)0.0049 (11)
C100.0187 (11)0.0142 (10)0.0157 (11)0.0019 (9)0.0008 (9)0.0007 (8)
C50.0277 (13)0.0174 (11)0.0207 (12)0.0071 (10)0.0009 (10)0.0017 (9)
C90.0199 (12)0.0192 (11)0.0177 (12)0.0040 (9)0.0008 (9)0.0001 (9)
C8A0.0271 (13)0.0281 (13)0.0158 (12)0.0085 (11)0.0033 (10)0.0004 (10)
C19A0.0354 (15)0.0293 (14)0.0195 (13)0.0131 (12)0.0072 (11)0.0062 (10)
C1A0.0424 (17)0.0262 (14)0.0288 (15)0.0172 (13)0.0071 (12)0.0120 (11)
C9A0.0196 (11)0.0187 (11)0.0160 (11)0.0042 (9)0.0008 (9)0.0005 (9)
C17A0.0252 (13)0.0208 (12)0.0161 (11)0.0054 (10)0.0037 (9)0.0046 (9)
C13A0.0230 (13)0.0244 (13)0.0291 (14)0.0082 (11)0.0018 (10)0.0012 (11)
C14A0.0257 (14)0.0306 (14)0.0272 (14)0.0099 (11)0.0071 (11)0.0003 (11)
C20A0.0431 (17)0.0305 (15)0.0202 (13)0.0151 (13)0.0075 (12)0.0121 (11)
C30.0202 (12)0.0150 (11)0.0234 (12)0.0062 (9)0.0023 (9)0.0056 (9)
C20.0300 (14)0.0283 (14)0.0313 (15)0.0169 (12)0.0048 (11)0.0043 (11)
C200.0313 (15)0.0313 (15)0.0333 (16)0.0165 (12)0.0042 (12)0.0093 (12)
C10.0322 (15)0.0346 (16)0.0412 (17)0.0225 (13)0.0016 (13)0.0076 (13)
C60.0493 (19)0.0254 (14)0.0317 (16)0.0184 (14)0.0024 (13)0.0095 (12)
C70.060 (2)0.0389 (18)0.0242 (15)0.0228 (16)0.0069 (14)0.0146 (13)
C6B0.050 (2)0.047 (2)0.064 (2)0.0221 (16)0.0032 (17)0.0032 (17)
C5B0.0359 (8)0.0359 (8)0.0299 (8)0.0133 (7)0.0031 (6)0.0044 (6)
C2B0.0301 (13)0.0338 (14)0.0239 (12)0.0119 (11)0.0061 (10)0.0046 (10)
O130.0352 (10)0.0208 (9)0.0377 (11)0.0085 (8)0.0035 (8)0.0055 (8)
C4B0.0359 (8)0.0359 (8)0.0299 (8)0.0133 (7)0.0031 (6)0.0044 (6)
C3B0.0210 (11)0.0203 (10)0.0191 (11)0.0044 (9)0.0017 (9)0.0001 (9)
C1B0.050 (2)0.047 (2)0.064 (2)0.0221 (16)0.0032 (17)0.0032 (17)
O150.0513 (13)0.0439 (12)0.0392 (12)0.0288 (11)0.0124 (10)0.0003 (9)
O140.0270 (13)0.092 (2)0.0654 (19)0.0124 (14)0.0095 (13)0.0062 (17)
O0AA0.0275 (10)0.0191 (9)0.0322 (11)0.0039 (8)0.0013 (8)0.0030 (8)
Geometric parameters (Å, º) top
Ga01—O41.8829 (18)C5A—C6A1.419 (4)
Ga01—O31.8941 (18)C5A—C4A1.436 (3)
Ga01—N12.009 (2)C16A—C17A1.441 (4)
Ga01—N22.022 (2)O7—N41.257 (3)
Ga01—O22.0262 (19)C6A—H6A0.9300
Ga01—O12.0644 (19)N1—C31.419 (3)
Ga02—O5A1.887 (2)C14—C131.397 (4)
Ga02—O4A1.8878 (18)C14—H140.9300
Ga02—N1A2.005 (2)C11—C121.417 (4)
Ga02—N2A2.019 (2)N1A—C4A1.298 (3)
Ga02—O0AA2.042 (2)C21A—H21D0.9600
Ga02—O2A2.0881 (19)C21A—H21E0.9600
O6—C121.373 (3)C21A—H21F0.9600
O6—C221.428 (3)N4—O91.236 (3)
N2A—C17A1.291 (4)C4A—H4A0.9300
N2A—C18A1.420 (3)C10A—C9A1.425 (3)
C7A—C6A1.368 (4)C19—C201.386 (4)
C7A—C8A1.405 (4)C19—H190.9300
C7A—H7A0.9300C18A—C19A1.393 (4)
O4—C111.319 (3)C12—C131.376 (4)
C15A—C14A1.363 (4)C13—H130.9300
C15A—C16A1.419 (4)C8—C91.377 (4)
C15A—H15A0.9300C8—C71.403 (5)
C12A—O251.373 (3)C8—H80.9300
C12A—C13A1.375 (4)C10—C51.415 (4)
C12A—C11A1.421 (4)C10—C91.422 (3)
O3—C101.315 (3)C5—C61.417 (4)
O5—C91.365 (3)C8A—C9A1.374 (4)
O5—C211.427 (3)C8A—H8A0.9300
C4—N11.296 (3)C19A—C20A1.386 (4)
C4—C51.433 (4)C19A—H19A0.9300
C4—H40.9300C1A—C20A1.385 (4)
C21—H21A0.9600C1A—H1AA0.9300
C21—H21B0.9600C17A—H17A0.9300
C21—H21C0.9600C13A—C14A1.407 (4)
C18—C191.398 (3)C13A—H13A0.9300
C18—C31.405 (4)C14A—H14A0.9300
C18—N21.417 (3)C20A—H20A0.9300
O25—C22A1.424 (4)C3—C21.393 (4)
O6A—C9A1.369 (3)C2—C11.382 (4)
O6A—C21A1.431 (3)C2—H20.9300
O1—H1A0.854 (19)C20—C11.388 (5)
O1—H1B0.850 (19)C20—H200.9300
C17—N21.293 (3)C1—H10.9300
C17—C161.437 (4)C6—C71.364 (5)
C17—H170.9300C6—H60.9300
O16—N41.253 (3)C7—H70.9300
C22—H22A0.9600C6B—C5B1.517 (5)
C22—H22B0.9600C6B—H6BA0.9600
C22—H22C0.9600C6B—H6BB0.9600
O2A—H2AA0.832 (19)C6B—H6BC0.9600
O2A—H2AB0.838 (19)C5B—O141.302 (5)
C2A—C1A1.386 (4)C5B—H5BA0.9700
C2A—C3A1.395 (4)C5B—H5BB0.9700
C2A—H2AC0.9300C2B—C4B1.252 (10)
O5A—C11A1.323 (3)C2B—H2BA0.9600
C15—C141.365 (4)C2B—H2BB0.9600
C15—C161.417 (4)C2B—H2BC0.9600
C15—H150.9300O13—C4B1.373 (8)
O4A—C10A1.313 (3)O13—H13B0.8200
O10—N31.240 (3)C4B—H4BA0.9700
C22A—H22D0.9600C4B—H4BB0.9700
C22A—H22E0.9600C3B—O151.369 (7)
C22A—H22F0.9600C3B—C1B1.575 (11)
C11A—C16A1.412 (3)C3B—H3BA0.9700
O2—H2A0.855 (19)C3B—H3BB0.9700
O2—H2B0.854 (19)C1B—H1BA0.9600
O11—N31.259 (3)C1B—H1BB0.9600
C3A—C18A1.412 (4)C1B—H1BC0.9600
C3A—N1A1.422 (3)O15—H15B0.8200
O12—N31.240 (3)O14—H14B0.8200
C16—C111.417 (3)O0AA—H0AA0.8624
C5A—C10A1.418 (4)O0AA—H0AB0.8623
O4—Ga01—O391.95 (8)O6A—C21A—H21E109.5
O4—Ga01—N1175.43 (8)H21D—C21A—H21E109.5
O3—Ga01—N192.60 (8)O6A—C21A—H21F109.5
O4—Ga01—N293.84 (8)H21D—C21A—H21F109.5
O3—Ga01—N2173.36 (8)H21E—C21A—H21F109.5
N1—Ga01—N281.59 (9)O9—N4—O16120.9 (3)
O4—Ga01—O290.60 (9)O9—N4—O7120.4 (2)
O3—Ga01—O293.72 (8)O16—N4—O7118.7 (2)
N1—Ga01—O289.56 (9)N1A—C4A—C5A125.2 (2)
N2—Ga01—O289.48 (8)N1A—C4A—H4A117.4
O4—Ga01—O189.74 (8)C5A—C4A—H4A117.4
O3—Ga01—O190.02 (7)C17—N2—C18123.5 (2)
N1—Ga01—O189.80 (8)C17—N2—Ga01123.54 (18)
N2—Ga01—O186.76 (8)C18—N2—Ga01112.92 (16)
O2—Ga01—O1176.23 (8)O4A—C10A—C5A125.0 (2)
O5A—Ga02—O4A91.11 (8)O4A—C10A—C9A117.0 (2)
O5A—Ga02—N1A174.56 (8)C5A—C10A—C9A118.0 (2)
O4A—Ga02—N1A93.96 (8)C20—C19—C18119.7 (3)
O5A—Ga02—N2A92.88 (8)C20—C19—H19120.1
O4A—Ga02—N2A174.46 (9)C18—C19—H19120.1
N1A—Ga02—N2A82.20 (9)C19A—C18A—C3A119.5 (2)
O5A—Ga02—O0AA89.90 (9)C19A—C18A—N2A124.5 (3)
O4A—Ga02—O0AA91.77 (8)C3A—C18A—N2A115.9 (2)
N1A—Ga02—O0AA87.98 (9)O6—C12—C13125.4 (2)
N2A—Ga02—O0AA92.08 (9)O6—C12—C11113.6 (2)
O5A—Ga02—O2A92.01 (8)C13—C12—C11121.0 (2)
O4A—Ga02—O2A89.17 (8)C12—C13—C14120.4 (3)
N1A—Ga02—O2A90.03 (9)C12—C13—H13119.8
N2A—Ga02—O2A86.84 (8)C14—C13—H13119.8
O0AA—Ga02—O2A177.85 (8)C9—C8—C7120.0 (3)
C12—O6—C22117.4 (2)C9—C8—H8120.0
C17A—N2A—C18A122.1 (2)C7—C8—H8120.0
C17A—N2A—Ga02124.87 (18)O3—C10—C5125.0 (2)
C18A—N2A—Ga02112.76 (17)O3—C10—C9116.9 (2)
C6A—C7A—C8A120.2 (3)C5—C10—C9118.0 (2)
C6A—C7A—H7A119.9C10—C5—C6119.7 (2)
C8A—C7A—H7A119.9C10—C5—C4123.7 (2)
C11—O4—Ga01127.10 (16)C6—C5—C4116.5 (2)
C14A—C15A—C16A120.9 (3)O5—C9—C8125.3 (2)
C14A—C15A—H15A119.5O5—C9—C10113.8 (2)
C16A—C15A—H15A119.5C8—C9—C10121.0 (2)
O25—C12A—C13A125.7 (3)C9A—C8A—C7A120.0 (2)
O25—C12A—C11A113.2 (2)C9A—C8A—H8A120.0
C13A—C12A—C11A121.2 (2)C7A—C8A—H8A120.0
C10—O3—Ga01126.03 (15)C20A—C19A—C18A120.0 (3)
C9—O5—C21116.6 (2)C20A—C19A—H19A120.0
N1—C4—C5124.8 (2)C18A—C19A—H19A120.0
N1—C4—H4117.6C20A—C1A—C2A120.6 (3)
C5—C4—H4117.6C20A—C1A—H1AA119.7
O5—C21—H21A109.5C2A—C1A—H1AA119.7
O5—C21—H21B109.5O6A—C9A—C8A125.2 (2)
H21A—C21—H21B109.5O6A—C9A—C10A113.4 (2)
O5—C21—H21C109.5C8A—C9A—C10A121.4 (2)
H21A—C21—H21C109.5N2A—C17A—C16A125.4 (2)
H21B—C21—H21C109.5N2A—C17A—H17A117.3
C19—C18—C3119.4 (2)C16A—C17A—H17A117.3
C19—C18—N2125.0 (2)C12A—C13A—C14A120.5 (3)
C3—C18—N2115.6 (2)C12A—C13A—H13A119.8
C12A—O25—C22A116.8 (2)C14A—C13A—H13A119.8
C9A—O6A—C21A117.0 (2)C15A—C14A—C13A119.7 (3)
Ga01—O1—H1A107 (4)C15A—C14A—H14A120.1
Ga01—O1—H1B107 (4)C13A—C14A—H14A120.1
H1A—O1—H1B110 (3)C1A—C20A—C19A120.4 (3)
N2—C17—C16125.5 (2)C1A—C20A—H20A119.8
N2—C17—H17117.3C19A—C20A—H20A119.8
C16—C17—H17117.3C2—C3—C18120.3 (2)
O6—C22—H22A109.5C2—C3—N1123.9 (2)
O6—C22—H22B109.5C18—C3—N1115.8 (2)
H22A—C22—H22B109.5C1—C2—C3119.5 (3)
O6—C22—H22C109.5C1—C2—H2120.3
H22A—C22—H22C109.5C3—C2—H2120.3
H22B—C22—H22C109.5C19—C20—C1120.4 (3)
Ga02—O2A—H2AA111 (4)C19—C20—H20119.8
Ga02—O2A—H2AB109 (4)C1—C20—H20119.8
H2AA—O2A—H2AB113 (3)C2—C1—C20120.7 (3)
C1A—C2A—C3A119.7 (3)C2—C1—H1119.6
C1A—C2A—H2AC120.2C20—C1—H1119.6
C3A—C2A—H2AC120.2C7—C6—C5120.4 (3)
C11A—O5A—Ga02127.81 (16)C7—C6—H6119.8
C14—C15—C16121.1 (3)C5—C6—H6119.8
C14—C15—H15119.4C6—C7—C8120.6 (3)
C16—C15—H15119.4C6—C7—H7119.7
C10A—O4A—Ga02127.15 (16)C8—C7—H7119.7
O25—C22A—H22D109.5C5B—C6B—H6BA109.5
O25—C22A—H22E109.5C5B—C6B—H6BB109.5
H22D—C22A—H22E109.5H6BA—C6B—H6BB109.5
O25—C22A—H22F109.5C5B—C6B—H6BC109.5
H22D—C22A—H22F109.5H6BA—C6B—H6BC109.5
H22E—C22A—H22F109.5H6BB—C6B—H6BC109.5
O5A—C11A—C16A125.6 (2)O14—C5B—C6B112.8 (3)
O5A—C11A—C12A116.7 (2)O14—C5B—H5BA109.0
C16A—C11A—C12A117.8 (2)C6B—C5B—H5BA109.0
Ga01—O2—H2A126 (3)O14—C5B—H5BB109.0
Ga01—O2—H2B121 (3)C6B—C5B—H5BB109.0
H2A—O2—H2B108 (3)H5BA—C5B—H5BB107.8
C2A—C3A—C18A119.7 (2)C4B—C2B—H2BA109.5
C2A—C3A—N1A124.9 (3)C4B—C2B—H2BB109.5
C18A—C3A—N1A115.4 (2)H2BA—C2B—H2BB109.5
C15—C16—C11119.2 (3)C4B—C2B—H2BC109.5
C15—C16—C17116.7 (2)H2BA—C2B—H2BC109.5
C11—C16—C17124.0 (2)H2BB—C2B—H2BC109.5
C10A—C5A—C6A119.3 (2)C4B—O13—H13B109.5
C10A—C5A—C4A124.1 (2)C2B—C4B—O13110.5 (6)
C6A—C5A—C4A116.6 (2)C2B—C4B—H4BA109.5
C11A—C16A—C15A119.9 (2)O13—C4B—H4BA109.5
C11A—C16A—C17A123.2 (2)C2B—C4B—H4BB109.5
C15A—C16A—C17A116.9 (2)O13—C4B—H4BB109.5
C7A—C6A—C5A121.1 (3)H4BA—C4B—H4BB108.1
C7A—C6A—H6A119.5O15—C3B—C1B130.8 (6)
C5A—C6A—H6A119.5O15—C3B—H3BA104.6
C4—N1—C3122.7 (2)C1B—C3B—H3BA104.6
C4—N1—Ga01123.77 (18)O15—C3B—H3BB104.6
C3—N1—Ga01113.12 (17)C1B—C3B—H3BB104.6
C15—C14—C13120.0 (3)H3BA—C3B—H3BB105.7
C15—C14—H14120.0C3B—C1B—H1BA109.5
C13—C14—H14120.0C3B—C1B—H1BB109.5
O4—C11—C12116.8 (2)H1BA—C1B—H1BB109.5
O4—C11—C16125.0 (2)C3B—C1B—H1BC109.5
C12—C11—C16118.1 (2)H1BA—C1B—H1BC109.5
C4A—N1A—C3A122.4 (2)H1BB—C1B—H1BC109.5
C4A—N1A—Ga02124.02 (18)C3B—O15—H15B109.5
C3A—N1A—Ga02113.50 (17)C5B—O14—H14B109.5
O12—N3—O10120.8 (3)Ga02—O0AA—H0AA110.3
O12—N3—O11118.1 (2)Ga02—O0AA—H0AB110.0
O10—N3—O11121.0 (3)H0AA—O0AA—H0AB103.7
O6A—C21A—H21D109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1B···O4i0.85 (2)2.11 (4)2.800 (2)138 (4)
O1—H1A···O3i0.85 (2)2.06 (3)2.816 (3)147 (5)
O2A—H2AB···O5Aii0.84 (2)2.17 (4)2.872 (3)141 (5)
O2A—H2AA···O4Aii0.83 (2)2.20 (4)2.844 (3)134 (5)
O2—H2B···O160.85 (2)1.90 (2)2.727 (3)161 (5)
O2—H2A···O13iii0.86 (2)1.77 (2)2.620 (5)170 (6)
O2—H2A···O15iii0.86 (2)1.83 (3)2.656 (6)162 (6)
Symmetry codes: (i) x+1, y, z+2; (ii) x, y+1, z+1; (iii) x, y, z+1.
Selected intramolecular hydrogen (bonds (Å, °) for 1 and 2 top
Complex 1
O5—H52···O160.87 (2)1.83 (3)2.684 (3)169 (3)
O11—H11B···O1A0.83 (3)1.73 (3)2.573 (4)178 (7)
Complex 2
O2—H2B···O70.85 (3)2.47 (4)3.116 (3)134 (5)
O2—H2B···O160.85 (3)1.91 (4)2.727 (3)161 (6)
Geometrical parameters (Å, °) for ππ stacking for 1 and 2 top
ComplexCgia[Res]-CgjbRccR1vdR2veAfBgΓh
1Cg5[2]⋯Cg6iii3.654 (3)-3.3184 (10)-3.3995 (12)7.61 (15)24.7321.49
2Cg1[2]⋯Cg2i3.972 (5)3.7819 (11)3.1648 (11)19.59 (18)17.8137.18
Cg3[2]⋯Cg4ii3.703 (4)3.4169 (13)3.3194 (18)7.64 (13)22.6826.31
Symmetry codes (i) -x, -y+1, -z; (ii) x, y-1, z-1; (iii) -x+1, -y, -z+1.

For 1, Cg5 and Cg6 are the centroids of the C8–C13 and C14–C19 rings, respectively. For 2, Cg1, Cg2, Cg3 and Cg4 are the centroids of the C1–C3/C18–C20, C1A–C3A/C18A–C20A, C5A–C10A and C11A–C16A rings, respectively; (b) [Res] = Residue; (c) Residue–centroid distance between ring i and ring j; (d) vertical distance from ring centroid i to ring j; (e) vertical distance from ring centroid j to ring i; (f) dihedral angle between the first ring mean plane and the second ring mean plane of the partner molecule; (g) angle between the centroid of the first ring and the second ring; (h) angle between the centroid of the first ring and the normal to the mean plane of the second ring of the partner molecule.
Geometrical parameters (Å, °) for X—H···π interactions top
ComplexX—H(I)Res(I)Cg(J)H···CgX—H···CgY···Cg
1C021—H02Aii[1] Cg22.86 (8)1703.817 (3)
2C21—H21Bi[1] Cg112.80 (2)1623.729 (3)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x, y, z-1.
Selected experimental and DFT-calculated geometric parameters (Å, °) for the indicated complexes top
ComplexBondBond length via XRDBond length via DFTAngleBond angle via XRDBond angle via DFT
Complex 1N01—Al12.007 (2)2.007O2—Al1—O193.64 (8)94.5
N02—Al11.988 (2)1.987O2—Al1—N0193.08 (9)92.8
O1—Al11.8197 (19)1.820N02—Al1—N0181.16 (9)81.6
O2—Al11.8066 (19)1.807O1—Al1—N0292.09 (9)91.6
Complex 2O5A—Ga021.887 (2)1.891O4A—Ga02—O5A91.11 (8)91.5
O4A—Ga021.8878 (18)1.889O5A—Ga02—N2A92.88 (8)93.1
N2A—Ga022.019 (2)2.022N2A—Ga02—N1A82.20 (9)81.9
N1A—Ga022.005 (2)2.009N1A—Ga02—O4A93.96 (8)94.2
 

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