Single crystals of the aluminium and gallium complexes of 6,6′-{(1
E,1′
E)-[1,2-phenylenebis(azanylylidene)]bis(methanylylidene)}bis(2-methoxyphenol), namely diaqua(6,6′-{(1
E,1′
E)-[1,2-phenylenebis(azanylylidene)]bis(methanylylidene)}bis(2-methoxyphenolato)-κ
4O1,
N,
N′,
O1′)aluminium(III) nitrate ethanol monosolvate, [Al(C
22H
18N
2O
4)(H
2O)
2]NO
3·C
2H
5OH,
1, and diaqua(6,6′-{(1
E,1′
E)-[1,2-phenylenebis(azanylylidene)]bis(methanylylidene)}bis(2-methoxyphenolato)-κ
4O1,
N,
N′,
O1′)gallium(III) nitrate ethanol monosolvate, [Ga(C
22H
18N
2O
4)(H
2O)
2]NO
3·C
2H
5OH,
2, were obtained after successful synthesis in ethanol. Both complexes crystallized in the triclinic space group
P
, 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
CCDC references: 1935699; 1935698
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'-{(1
E,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·C2H6O | Z = 4 |
Mr = 545.47 | F(000) = 1144 |
Triclinic, P1 | Dx = 1.476 Mg m−3 |
a = 12.413 (5) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 13.394 (5) Å | Cell parameters from 9867 reflections |
c = 16.368 (5) Å | θ = 1.0–1.0° |
α = 87.899 (5)° | µ = 0.15 mm−1 |
β = 79.578 (5)° | T = 100 K |
γ = 66.635 (5)° | Cuboid, yellow |
V = 2455.1 (15) Å3 | 0.30 × 0.27 × 0.13 mm |
Data collection top
Bruker APEXII CCD diffractometer | Rint = 0.062 |
φ and ω scans | θmax = 28.0°, θmin = 1.7° |
64029 measured reflections | h = −16→12 |
11817 independent reflections | k = −17→17 |
7331 reflections with I > 2σ(I) | l = −21→21 |
Refinement top
Refinement on F2 | 19 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.056 | H 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 reflections | Δρmax = 0.80 e Å−3 |
718 parameters | Δρmin = −0.76 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.5080 (2) | 0.3196 (2) | 0.35492 (16) | 0.0242 (6) | |
C5A | 0.9140 (2) | 0.1954 (2) | 0.08411 (17) | 0.0224 (6) | |
C1T | 0.0336 (4) | 0.2269 (4) | 0.5388 (3) | 0.0752 (14) | |
H1T1 | 0.1042 | 0.1691 | 0.5528 | 0.090* | |
H1T2 | 0.0057 | 0.1971 | 0.4979 | 0.090* | |
C4A | 0.8417 (3) | 0.1404 (2) | 0.07802 (19) | 0.0297 (6) | |
H4A | 0.8370 | 0.1180 | 0.0262 | 0.036* | |
C2 | 0.5570 (3) | 0.3951 (2) | 0.32735 (18) | 0.0309 (7) | |
H2 | 0.5862 | 0.4250 | 0.3640 | 0.037* | |
C2T | −0.0622 (4) | 0.2631 (4) | 0.6162 (3) | 0.0695 (12) | |
H2TA | −0.0398 | 0.3009 | 0.6544 | 0.104* | |
H2TB | −0.0709 | 0.2005 | 0.6420 | 0.104* | |
H2TC | −0.1366 | 0.3107 | 0.6013 | 0.104* | |
C3 | 0.5619 (3) | 0.4253 (2) | 0.24553 (19) | 0.0345 (7) | |
H3 | 0.5935 | 0.4763 | 0.2276 | 0.041* | |
C3A | 0.7767 (3) | 0.1189 (2) | 0.1491 (2) | 0.0351 (7) | |
H3A | 0.7283 | 0.0818 | 0.1451 | 0.042* | |
C4 | 0.5199 (3) | 0.3800 (2) | 0.18989 (18) | 0.0343 (7) | |
H4 | 0.5256 | 0.3993 | 0.1346 | 0.041* | |
C2A | 0.7835 (3) | 0.1526 (2) | 0.2262 (2) | 0.0349 (7) | |
H2A | 0.7404 | 0.1369 | 0.2738 | 0.042* | |
C1A | 0.8534 (3) | 0.2090 (2) | 0.23351 (18) | 0.0282 (6) | |
H1A | 0.8564 | 0.2322 | 0.2856 | 0.034* | |
C5 | 0.4696 (3) | 0.3064 (2) | 0.21672 (18) | 0.0319 (7) | |
H5 | 0.4420 | 0.2758 | 0.1794 | 0.038* | |
C20A | 0.9197 (2) | 0.2309 (2) | 0.16182 (17) | 0.0226 (6) | |
C6 | 0.4603 (2) | 0.2781 (2) | 0.29950 (17) | 0.0255 (6) | |
C7 | 0.3410 (3) | 0.1778 (2) | 0.29453 (17) | 0.0265 (6) | |
H7 | 0.3340 | 0.2031 | 0.2413 | 0.032* | |
C19A | 1.0190 (2) | 0.3174 (2) | 0.22613 (16) | 0.0228 (6) | |
H19A | 0.9933 | 0.2917 | 0.2762 | 0.027* | |
C18A | 1.0854 (2) | 0.3842 (2) | 0.22816 (16) | 0.0223 (6) | |
C8 | 0.2809 (2) | 0.1087 (2) | 0.32543 (17) | 0.0243 (6) | |
C17A | 1.1076 (3) | 0.4048 (2) | 0.30642 (18) | 0.0320 (7) | |
H17A | 1.0837 | 0.3719 | 0.3531 | 0.038* | |
C9 | 0.2189 (3) | 0.0800 (2) | 0.27187 (18) | 0.0280 (6) | |
H9 | 0.2180 | 0.1070 | 0.2187 | 0.034* | |
C16A | 1.1634 (3) | 0.4719 (3) | 0.31399 (19) | 0.0375 (7) | |
H16A | 1.1795 | 0.4831 | 0.3654 | 0.045* | |
C10 | 0.1608 (3) | 0.0138 (2) | 0.29680 (19) | 0.0319 (7) | |
H10 | 0.1201 | −0.0039 | 0.2611 | 0.038* | |
C11 | 0.1625 (3) | −0.0279 (2) | 0.37686 (18) | 0.0304 (6) | |
H11 | 0.1226 | −0.0730 | 0.3941 | 0.036* | |
C15A | 1.1970 (3) | 0.5246 (2) | 0.24454 (18) | 0.0312 (7) | |
H15A | 1.2340 | 0.5716 | 0.2503 | 0.037* | |
C14A | 1.1755 (2) | 0.5069 (2) | 0.16792 (16) | 0.0232 (6) | |
C12 | 0.2228 (2) | −0.0021 (2) | 0.42984 (17) | 0.0264 (6) | |
C13A | 1.1224 (2) | 0.4335 (2) | 0.15751 (15) | 0.0189 (5) | |
C13 | 0.2825 (2) | 0.0675 (2) | 0.40557 (16) | 0.0226 (6) | |
C14 | 0.4968 (2) | 0.1922 (2) | 0.60431 (16) | 0.0224 (6) | |
C12A | 1.1073 (2) | 0.2922 (2) | −0.13148 (16) | 0.0206 (5) | |
C11A | 1.1604 (2) | 0.3190 (2) | −0.20851 (16) | 0.0230 (6) | |
C15 | 0.5028 (2) | 0.1578 (2) | 0.68710 (16) | 0.0227 (6) | |
C10A | 1.1856 (3) | 0.2562 (2) | −0.27980 (18) | 0.0341 (7) | |
H10A | 1.2233 | 0.2734 | −0.3294 | 0.041* | |
C16 | 0.5523 (3) | 0.1992 (2) | 0.73854 (17) | 0.0276 (6) | |
H16 | 0.5559 | 0.1753 | 0.7924 | 0.033* | |
C9A | 1.1544 (3) | 0.1664 (3) | −0.2774 (2) | 0.0429 (8) | |
H9A | 1.1738 | 0.1227 | −0.3251 | 0.051* | |
C17 | 0.5973 (3) | 0.2776 (2) | 0.70969 (18) | 0.0307 (6) | |
H17 | 0.6306 | 0.3057 | 0.7446 | 0.037* | |
C8A | 1.0957 (3) | 0.1423 (2) | −0.20543 (19) | 0.0370 (7) | |
H8A | 1.0715 | 0.0848 | −0.2053 | 0.044* | |
C18 | 0.5923 (3) | 0.3129 (2) | 0.63031 (17) | 0.0279 (6) | |
H18 | 0.6225 | 0.3648 | 0.6118 | 0.034* | |
C7A | 1.0715 (2) | 0.2045 (2) | −0.13123 (17) | 0.0254 (6) | |
C19 | 0.5422 (2) | 0.2716 (2) | 0.57628 (16) | 0.0229 (6) | |
C6A | 1.0075 (2) | 0.1765 (2) | −0.05780 (17) | 0.0236 (6) | |
H6A | 0.9814 | 0.1212 | −0.0630 | 0.028* | |
C20 | 0.5427 (2) | 0.3105 (2) | 0.49339 (17) | 0.0242 (6) | |
H20 | 0.5748 | 0.3623 | 0.4796 | 0.029* | |
C021 | 1.2292 (3) | 0.4467 (2) | −0.28041 (17) | 0.0296 (6) | |
H02A | 1.3074 | 0.3945 | −0.3033 | 0.044* | |
H02B | 1.2332 | 0.5154 | −0.2708 | 0.044* | |
H02C | 1.1764 | 0.4554 | −0.3188 | 0.044* | |
C21 | 0.1731 (3) | −0.1105 (3) | 0.5381 (2) | 0.0380 (7) | |
H21A | 0.0886 | −0.0724 | 0.5411 | 0.057* | |
H21B | 0.1892 | −0.1341 | 0.5923 | 0.057* | |
H21C | 0.2023 | −0.1726 | 0.5004 | 0.057* | |
C22 | 0.4375 (3) | 0.0573 (3) | 0.79402 (17) | 0.0331 (7) | |
H22A | 0.5126 | 0.0259 | 0.8127 | 0.050* | |
H22B | 0.3993 | 0.0069 | 0.8015 | 0.050* | |
H22C | 0.3874 | 0.1235 | 0.8257 | 0.050* | |
C022 | 1.2547 (3) | 0.6319 (2) | 0.10115 (19) | 0.0314 (7) | |
H02D | 1.2020 | 0.6898 | 0.1403 | 0.047* | |
H02E | 1.2669 | 0.6611 | 0.0475 | 0.047* | |
H02F | 1.3299 | 0.5966 | 0.1192 | 0.047* | |
N01 | 0.99260 (19) | 0.29061 (16) | 0.15943 (13) | 0.0201 (5) | |
N02 | 0.98374 (19) | 0.22294 (16) | 0.01499 (13) | 0.0201 (5) | |
N03 | 0.5016 (2) | 0.27866 (17) | 0.43608 (13) | 0.0225 (5) | |
N04 | 0.4048 (2) | 0.20796 (17) | 0.33505 (14) | 0.0242 (5) | |
N07 | 1.2872 (2) | −0.06382 (18) | 0.07667 (15) | 0.0290 (5) | |
N08 | 0.7856 (2) | 0.43557 (19) | 0.45715 (14) | 0.0286 (5) | |
O1 | 1.09202 (16) | 0.35187 (13) | −0.06456 (11) | 0.0204 (4) | |
O1A | 0.0628 (2) | 0.3039 (3) | 0.5058 (2) | 0.0765 (9) | |
H1AA | 0.0025 | 0.3565 | 0.4995 | 0.115* | |
O2 | 1.10899 (16) | 0.41676 (14) | 0.08147 (10) | 0.0203 (4) | |
O3 | 1.20306 (17) | 0.55492 (14) | 0.09594 (11) | 0.0249 (4) | |
O4 | 1.18555 (16) | 0.40955 (14) | −0.20349 (11) | 0.0238 (4) | |
O5 | 1.20062 (17) | 0.20279 (15) | 0.04417 (13) | 0.0256 (4) | |
O6 | 0.89451 (16) | 0.44340 (14) | 0.05168 (11) | 0.0199 (4) | |
O7 | 0.33834 (17) | 0.08916 (14) | 0.46022 (11) | 0.0245 (4) | |
O8 | 0.44928 (17) | 0.14838 (14) | 0.55821 (11) | 0.0248 (4) | |
O9 | 0.45715 (17) | 0.08044 (15) | 0.70789 (11) | 0.0259 (4) | |
O10 | 0.23163 (18) | −0.03909 (15) | 0.50890 (12) | 0.0295 (4) | |
O11 | 0.2739 (2) | 0.30139 (17) | 0.48967 (13) | 0.0324 (5) | |
O12 | 0.57291 (18) | 0.05570 (15) | 0.40929 (12) | 0.0251 (4) | |
O13 | 0.6790 (2) | 0.49714 (18) | 0.47098 (16) | 0.0496 (6) | |
O14 | 0.8200 (2) | 0.34409 (16) | 0.42420 (13) | 0.0372 (5) | |
O15 | 0.8595 (2) | 0.4692 (2) | 0.47657 (15) | 0.0478 (6) | |
O16 | 1.18516 (17) | 0.01059 (15) | 0.07687 (13) | 0.0325 (5) | |
O18 | 1.2986 (2) | −0.15766 (16) | 0.09207 (15) | 0.0413 (6) | |
Al1 | 1.05248 (7) | 0.32514 (6) | 0.04415 (5) | 0.01802 (17) | |
Al2 | 0.41964 (7) | 0.17640 (6) | 0.45372 (5) | 0.02215 (19) | |
C4R | 1.4110 (4) | 0.3722 (3) | −0.0676 (2) | 0.0651 (12) | |
H4R1 | 1.4261 | 0.4338 | −0.0534 | 0.098* | |
H4R2 | 1.3324 | 0.3968 | −0.0806 | 0.098* | |
H4R3 | 1.4689 | 0.3330 | −0.1149 | 0.098* | |
O4T | 1.4043 (5) | 0.2113 (3) | −0.0212 (3) | 0.0478 (6) | 0.5 |
H4T | 1.4649 | 0.1696 | −0.0512 | 0.072* | 0.5 |
C4T | 1.4190 (11) | 0.3067 (5) | −0.0030 (6) | 0.0478 (6) | 0.5 |
H4T1 | 1.3585 | 0.3460 | 0.0440 | 0.057* | 0.5 |
H4T2 | 1.4964 | 0.2868 | 0.0127 | 0.057* | 0.5 |
O4U | 1.4144 (5) | 0.2145 (3) | 0.0158 (3) | 0.0496 (6) | 0.5 |
H4U | 1.4471 | 0.1796 | −0.0283 | 0.074* | 0.5 |
C4U | 1.4270 (10) | 0.3121 (6) | 0.0117 (6) | 0.0496 (6) | 0.5 |
H4U1 | 1.5061 | 0.2989 | 0.0219 | 0.059* | 0.5 |
H4U2 | 1.3700 | 0.3598 | 0.0568 | 0.059* | 0.5 |
O17 | 1.37647 (19) | −0.04004 (17) | 0.06044 (16) | 0.0444 (6) | |
H52 | 1.203 (3) | 0.1372 (18) | 0.049 (2) | 0.048 (10)* | |
H51 | 1.269 (2) | 0.200 (4) | 0.021 (3) | 0.097 (18)* | |
H61 | 0.879 (3) | 0.461 (3) | 0.0022 (14) | 0.056 (12)* | |
H62 | 0.891 (3) | 0.500 (2) | 0.077 (2) | 0.049 (11)* | |
H11B | 0.205 (2) | 0.301 (3) | 0.494 (2) | 0.061 (13)* | |
H11A | 0.269 (4) | 0.364 (2) | 0.496 (3) | 0.071 (14)* | |
H12B | 0.563 (3) | 0.003 (2) | 0.389 (2) | 0.045 (10)* | |
H12A | 0.620 (3) | 0.028 (3) | 0.443 (2) | 0.081 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0277 (14) | 0.0180 (13) | 0.0214 (14) | −0.0039 (11) | −0.0039 (11) | 0.0037 (10) |
C5A | 0.0218 (13) | 0.0152 (12) | 0.0275 (14) | −0.0058 (10) | −0.0028 (11) | 0.0080 (10) |
C1T | 0.057 (3) | 0.085 (3) | 0.057 (3) | 0.001 (3) | −0.009 (2) | −0.007 (3) |
C4A | 0.0304 (16) | 0.0283 (15) | 0.0336 (16) | −0.0148 (13) | −0.0068 (12) | 0.0061 (12) |
C2 | 0.0418 (18) | 0.0234 (14) | 0.0290 (15) | −0.0134 (13) | −0.0101 (13) | 0.0061 (12) |
C2T | 0.065 (3) | 0.061 (3) | 0.075 (3) | −0.020 (2) | −0.006 (2) | 0.003 (2) |
C3 | 0.0456 (19) | 0.0253 (15) | 0.0347 (17) | −0.0170 (14) | −0.0075 (14) | 0.0119 (13) |
C3A | 0.0359 (17) | 0.0332 (16) | 0.0422 (18) | −0.0223 (14) | −0.0028 (14) | 0.0085 (14) |
C4 | 0.0455 (19) | 0.0335 (16) | 0.0252 (15) | −0.0163 (14) | −0.0107 (13) | 0.0143 (13) |
C2A | 0.0341 (17) | 0.0338 (16) | 0.0363 (17) | −0.0180 (14) | 0.0033 (13) | 0.0104 (13) |
C1A | 0.0313 (16) | 0.0252 (14) | 0.0271 (15) | −0.0125 (12) | −0.0011 (12) | 0.0086 (12) |
C5 | 0.0401 (17) | 0.0335 (16) | 0.0250 (15) | −0.0161 (14) | −0.0110 (13) | 0.0091 (12) |
C20A | 0.0211 (13) | 0.0165 (12) | 0.0266 (14) | −0.0048 (10) | −0.0030 (11) | 0.0084 (11) |
C6 | 0.0301 (15) | 0.0207 (13) | 0.0232 (14) | −0.0075 (11) | −0.0056 (11) | 0.0063 (11) |
C7 | 0.0319 (15) | 0.0221 (13) | 0.0203 (14) | −0.0049 (12) | −0.0068 (11) | 0.0060 (11) |
C19A | 0.0203 (13) | 0.0210 (13) | 0.0200 (13) | −0.0019 (11) | −0.0023 (10) | 0.0086 (10) |
C18A | 0.0242 (14) | 0.0213 (13) | 0.0185 (13) | −0.0056 (11) | −0.0059 (10) | 0.0055 (10) |
C8 | 0.0256 (14) | 0.0208 (13) | 0.0224 (14) | −0.0046 (11) | −0.0050 (11) | 0.0014 (11) |
C17A | 0.0365 (17) | 0.0397 (17) | 0.0225 (15) | −0.0173 (14) | −0.0087 (12) | 0.0107 (13) |
C9 | 0.0314 (16) | 0.0261 (14) | 0.0238 (14) | −0.0067 (12) | −0.0094 (12) | 0.0026 (11) |
C16A | 0.0474 (19) | 0.0491 (19) | 0.0236 (15) | −0.0240 (16) | −0.0143 (14) | 0.0062 (14) |
C10 | 0.0317 (16) | 0.0328 (16) | 0.0325 (16) | −0.0114 (13) | −0.0125 (13) | 0.0018 (13) |
C11 | 0.0281 (15) | 0.0285 (15) | 0.0339 (16) | −0.0114 (12) | −0.0040 (12) | 0.0022 (12) |
C15A | 0.0342 (16) | 0.0380 (17) | 0.0287 (16) | −0.0192 (14) | −0.0121 (13) | 0.0024 (13) |
C14A | 0.0200 (13) | 0.0227 (13) | 0.0239 (14) | −0.0053 (11) | −0.0043 (11) | 0.0035 (11) |
C12 | 0.0283 (15) | 0.0221 (13) | 0.0235 (14) | −0.0055 (12) | −0.0030 (11) | 0.0023 (11) |
C13A | 0.0162 (12) | 0.0159 (12) | 0.0200 (13) | −0.0011 (10) | −0.0047 (10) | 0.0026 (10) |
C13 | 0.0228 (14) | 0.0187 (13) | 0.0220 (14) | −0.0033 (11) | −0.0050 (11) | 0.0008 (10) |
C14 | 0.0231 (14) | 0.0173 (12) | 0.0203 (13) | −0.0017 (11) | −0.0026 (10) | −0.0024 (10) |
C12A | 0.0189 (13) | 0.0167 (12) | 0.0206 (13) | −0.0014 (10) | −0.0034 (10) | 0.0018 (10) |
C11A | 0.0236 (14) | 0.0193 (13) | 0.0232 (14) | −0.0059 (11) | −0.0040 (11) | 0.0036 (11) |
C15 | 0.0252 (14) | 0.0177 (12) | 0.0196 (13) | −0.0035 (11) | −0.0021 (11) | 0.0000 (10) |
C10A | 0.0394 (18) | 0.0361 (17) | 0.0220 (15) | −0.0144 (14) | 0.0055 (13) | −0.0032 (12) |
C16 | 0.0302 (15) | 0.0302 (15) | 0.0192 (14) | −0.0085 (12) | −0.0047 (11) | −0.0008 (11) |
C9A | 0.063 (2) | 0.0401 (18) | 0.0267 (16) | −0.0267 (17) | 0.0068 (15) | −0.0143 (14) |
C17 | 0.0367 (17) | 0.0340 (16) | 0.0249 (15) | −0.0166 (13) | −0.0075 (12) | −0.0011 (12) |
C8A | 0.051 (2) | 0.0291 (16) | 0.0327 (17) | −0.0210 (15) | 0.0010 (14) | −0.0082 (13) |
C18 | 0.0316 (16) | 0.0280 (14) | 0.0250 (15) | −0.0136 (12) | −0.0027 (12) | 0.0006 (12) |
C7A | 0.0295 (15) | 0.0187 (13) | 0.0252 (14) | −0.0080 (11) | −0.0021 (11) | 0.0012 (11) |
C19 | 0.0227 (14) | 0.0188 (13) | 0.0224 (14) | −0.0042 (11) | −0.0016 (11) | −0.0005 (10) |
C6A | 0.0268 (14) | 0.0149 (12) | 0.0271 (15) | −0.0066 (11) | −0.0041 (11) | 0.0029 (11) |
C20 | 0.0231 (14) | 0.0186 (13) | 0.0260 (14) | −0.0041 (11) | −0.0022 (11) | 0.0009 (11) |
C021 | 0.0285 (15) | 0.0305 (15) | 0.0244 (15) | −0.0102 (12) | 0.0033 (11) | 0.0082 (12) |
C21 | 0.0372 (18) | 0.0424 (18) | 0.0384 (18) | −0.0217 (15) | −0.0055 (14) | 0.0159 (15) |
C22 | 0.0419 (18) | 0.0403 (17) | 0.0208 (14) | −0.0205 (15) | −0.0063 (13) | 0.0084 (13) |
C022 | 0.0359 (17) | 0.0281 (15) | 0.0387 (17) | −0.0190 (13) | −0.0145 (13) | 0.0076 (13) |
N01 | 0.0203 (11) | 0.0157 (10) | 0.0215 (11) | −0.0047 (9) | −0.0038 (9) | 0.0078 (9) |
N02 | 0.0206 (11) | 0.0158 (10) | 0.0219 (11) | −0.0055 (9) | −0.0037 (9) | 0.0055 (9) |
N03 | 0.0255 (12) | 0.0188 (11) | 0.0177 (11) | −0.0036 (9) | −0.0033 (9) | 0.0038 (9) |
N04 | 0.0294 (13) | 0.0185 (11) | 0.0226 (12) | −0.0069 (10) | −0.0065 (10) | 0.0045 (9) |
N07 | 0.0304 (13) | 0.0187 (12) | 0.0391 (14) | −0.0074 (10) | −0.0150 (11) | 0.0034 (10) |
N08 | 0.0384 (15) | 0.0236 (12) | 0.0237 (12) | −0.0130 (11) | −0.0049 (10) | 0.0067 (10) |
O1 | 0.0237 (9) | 0.0173 (9) | 0.0188 (9) | −0.0069 (7) | −0.0034 (7) | 0.0028 (7) |
O1A | 0.0380 (16) | 0.099 (3) | 0.084 (2) | −0.0208 (16) | −0.0100 (15) | 0.024 (2) |
O2 | 0.0246 (10) | 0.0196 (9) | 0.0167 (9) | −0.0086 (8) | −0.0054 (7) | 0.0059 (7) |
O3 | 0.0308 (11) | 0.0233 (9) | 0.0254 (10) | −0.0155 (8) | −0.0068 (8) | 0.0058 (8) |
O4 | 0.0267 (10) | 0.0231 (9) | 0.0206 (10) | −0.0103 (8) | −0.0013 (8) | 0.0059 (7) |
O5 | 0.0206 (10) | 0.0169 (9) | 0.0363 (11) | −0.0057 (8) | −0.0033 (8) | 0.0077 (8) |
O6 | 0.0209 (9) | 0.0172 (9) | 0.0189 (10) | −0.0052 (7) | −0.0030 (7) | 0.0040 (8) |
O7 | 0.0310 (10) | 0.0226 (9) | 0.0201 (10) | −0.0097 (8) | −0.0082 (8) | 0.0055 (7) |
O8 | 0.0340 (11) | 0.0217 (9) | 0.0194 (9) | −0.0107 (8) | −0.0078 (8) | 0.0024 (7) |
O9 | 0.0349 (11) | 0.0256 (10) | 0.0179 (9) | −0.0131 (9) | −0.0043 (8) | 0.0037 (8) |
O10 | 0.0362 (11) | 0.0295 (10) | 0.0247 (10) | −0.0154 (9) | −0.0061 (8) | 0.0084 (8) |
O11 | 0.0342 (13) | 0.0217 (11) | 0.0334 (12) | −0.0043 (10) | −0.0028 (9) | 0.0033 (9) |
O12 | 0.0319 (11) | 0.0190 (10) | 0.0229 (10) | −0.0078 (8) | −0.0066 (9) | 0.0017 (8) |
O13 | 0.0346 (11) | 0.0331 (10) | 0.0604 (15) | 0.0043 (9) | 0.0002 (10) | 0.0015 (10) |
O14 | 0.0487 (14) | 0.0199 (10) | 0.0402 (13) | −0.0102 (9) | −0.0085 (10) | −0.0024 (9) |
O15 | 0.0620 (14) | 0.0528 (13) | 0.0459 (13) | −0.0404 (11) | −0.0113 (11) | 0.0024 (10) |
O16 | 0.0244 (11) | 0.0204 (10) | 0.0500 (13) | −0.0040 (8) | −0.0126 (9) | 0.0052 (9) |
O18 | 0.0480 (14) | 0.0181 (10) | 0.0614 (15) | −0.0122 (10) | −0.0224 (11) | 0.0103 (10) |
Al1 | 0.0185 (4) | 0.0146 (4) | 0.0191 (4) | −0.0051 (3) | −0.0031 (3) | 0.0054 (3) |
Al2 | 0.0274 (4) | 0.0183 (4) | 0.0188 (4) | −0.0069 (3) | −0.0051 (3) | 0.0040 (3) |
C4R | 0.052 (2) | 0.065 (3) | 0.045 (2) | 0.006 (2) | 0.0040 (18) | −0.0008 (19) |
O4T | 0.0620 (14) | 0.0528 (13) | 0.0459 (13) | −0.0404 (11) | −0.0113 (11) | 0.0024 (10) |
C4T | 0.0620 (14) | 0.0528 (13) | 0.0459 (13) | −0.0404 (11) | −0.0113 (11) | 0.0024 (10) |
O4U | 0.0346 (11) | 0.0331 (10) | 0.0604 (15) | 0.0043 (9) | 0.0002 (10) | 0.0015 (10) |
C4U | 0.0346 (11) | 0.0331 (10) | 0.0604 (15) | 0.0043 (9) | 0.0002 (10) | 0.0015 (10) |
O17 | 0.0264 (12) | 0.0281 (11) | 0.0793 (18) | −0.0105 (9) | −0.0118 (11) | 0.0024 (11) |
Geometric parameters (Å, º) top
C1—C2 | 1.396 (4) | C16—H16 | 0.9300 |
C1—C6 | 1.405 (4) | C9A—C8A | 1.367 (4) |
C1—N03 | 1.419 (3) | C9A—H9A | 0.9300 |
C5A—C4A | 1.385 (4) | C17—C18 | 1.370 (4) |
C5A—C20A | 1.398 (4) | C17—H17 | 0.9300 |
C5A—N02 | 1.426 (3) | C8A—C7A | 1.415 (4) |
C1T—O1A | 1.293 (6) | C8A—H8A | 0.9300 |
C1T—C2T | 1.517 (6) | C18—C19 | 1.409 (4) |
C1T—H1T1 | 0.9700 | C18—H18 | 0.9300 |
C1T—H1T2 | 0.9700 | C7A—C6A | 1.441 (4) |
C4A—C3A | 1.381 (4) | C19—C20 | 1.435 (4) |
C4A—H4A | 0.9300 | C6A—N02 | 1.294 (3) |
C2—C3 | 1.382 (4) | C6A—H6A | 0.9300 |
C2—H2 | 0.9300 | C20—N03 | 1.303 (4) |
C2T—H2TA | 0.9600 | C20—H20 | 0.9300 |
C2T—H2TB | 0.9600 | C021—O4 | 1.431 (3) |
C2T—H2TC | 0.9600 | C021—H02A | 0.9600 |
C3—C4 | 1.390 (4) | C021—H02B | 0.9600 |
C3—H3 | 0.9300 | C021—H02C | 0.9600 |
C3A—C2A | 1.384 (5) | C21—O10 | 1.436 (3) |
C3A—H3A | 0.9300 | C21—H21A | 0.9600 |
C4—C5 | 1.383 (4) | C21—H21B | 0.9600 |
C4—H4 | 0.9300 | C21—H21C | 0.9600 |
C2A—C1A | 1.379 (4) | C22—O9 | 1.431 (3) |
C2A—H2A | 0.9300 | C22—H22A | 0.9600 |
C1A—C20A | 1.399 (4) | C22—H22B | 0.9600 |
C1A—H1A | 0.9300 | C22—H22C | 0.9600 |
C5—C6 | 1.390 (4) | C022—O3 | 1.425 (3) |
C5—H5 | 0.9300 | C022—H02D | 0.9600 |
C20A—N01 | 1.420 (3) | C022—H02E | 0.9600 |
C6—N04 | 1.423 (3) | C022—H02F | 0.9600 |
C7—N04 | 1.301 (4) | N01—Al1 | 2.007 (2) |
C7—C8 | 1.430 (4) | N02—Al1 | 1.988 (2) |
C7—H7 | 0.9300 | N03—Al2 | 1.991 (2) |
C19A—N01 | 1.296 (3) | N04—Al2 | 1.998 (2) |
C19A—C18A | 1.442 (4) | N07—O18 | 1.229 (3) |
C19A—H19A | 0.9300 | N07—O17 | 1.252 (3) |
C18A—C13A | 1.406 (4) | N07—O16 | 1.263 (3) |
C18A—C17A | 1.417 (4) | N08—O13 | 1.233 (3) |
C8—C13 | 1.405 (4) | N08—O14 | 1.235 (3) |
C8—C9 | 1.418 (4) | N08—O15 | 1.261 (3) |
C17A—C16A | 1.354 (4) | O1—Al1 | 1.8197 (19) |
C17A—H17A | 0.9300 | O1A—H1AA | 0.8200 |
C9—C10 | 1.360 (4) | O2—Al1 | 1.8066 (19) |
C9—H9 | 0.9300 | O5—Al1 | 1.918 (2) |
C16A—C15A | 1.403 (4) | O5—H52 | 0.870 (18) |
C16A—H16A | 0.9300 | O5—H51 | 0.845 (19) |
C10—C11 | 1.406 (4) | O6—Al1 | 1.958 (2) |
C10—H10 | 0.9300 | O6—H61 | 0.871 (18) |
C11—C12 | 1.376 (4) | O6—H62 | 0.860 (18) |
C11—H11 | 0.9300 | O7—Al2 | 1.812 (2) |
C15A—C14A | 1.376 (4) | O8—Al2 | 1.809 (2) |
C15A—H15A | 0.9300 | O11—Al2 | 1.925 (2) |
C14A—O3 | 1.376 (3) | O11—H11B | 0.852 (19) |
C14A—C13A | 1.413 (4) | O11—H11A | 0.826 (19) |
C12—O10 | 1.376 (3) | O12—Al2 | 1.977 (2) |
C12—C13 | 1.411 (4) | O12—H12B | 0.852 (18) |
C13A—O2 | 1.324 (3) | O12—H12A | 0.848 (19) |
C13—O7 | 1.330 (3) | C4R—C4T | 1.340 (7) |
C14—O8 | 1.316 (3) | C4R—C4U | 1.504 (9) |
C14—C19 | 1.415 (4) | C4R—H4R1 | 0.9600 |
C14—C15 | 1.421 (4) | C4R—H4R2 | 0.9600 |
C12A—O1 | 1.321 (3) | C4R—H4R3 | 0.9600 |
C12A—C7A | 1.410 (4) | O4T—C4T | 1.410 (4) |
C12A—C11A | 1.417 (4) | O4T—H4T | 0.8200 |
C11A—O4 | 1.375 (3) | C4T—H4T1 | 0.9700 |
C11A—C10A | 1.378 (4) | C4T—H4T2 | 0.9700 |
C15—O9 | 1.372 (3) | O4U—C4U | 1.376 (9) |
C15—C16 | 1.372 (4) | O4U—H4U | 1.2082 |
C10A—C9A | 1.400 (4) | C4U—H4U1 | 0.9700 |
C10A—H10A | 0.9300 | C4U—H4U2 | 0.9700 |
C16—C17 | 1.404 (4) | | |
| | | |
C2—C1—C6 | 119.3 (2) | C18—C19—C14 | 119.5 (2) |
C2—C1—N03 | 125.6 (3) | C18—C19—C20 | 117.7 (2) |
C6—C1—N03 | 115.1 (2) | C14—C19—C20 | 122.8 (2) |
C4A—C5A—C20A | 120.2 (2) | N02—C6A—C7A | 124.5 (2) |
C4A—C5A—N02 | 124.6 (3) | N02—C6A—H6A | 117.8 |
C20A—C5A—N02 | 115.1 (2) | C7A—C6A—H6A | 117.8 |
O1A—C1T—C2T | 113.9 (4) | N03—C20—C19 | 124.8 (3) |
O1A—C1T—H1T1 | 108.8 | N03—C20—H20 | 117.6 |
C2T—C1T—H1T1 | 108.8 | C19—C20—H20 | 117.6 |
O1A—C1T—H1T2 | 108.8 | O4—C021—H02A | 109.5 |
C2T—C1T—H1T2 | 108.8 | O4—C021—H02B | 109.5 |
H1T1—C1T—H1T2 | 107.7 | H02A—C021—H02B | 109.5 |
C3A—C4A—C5A | 119.9 (3) | O4—C021—H02C | 109.5 |
C3A—C4A—H4A | 120.0 | H02A—C021—H02C | 109.5 |
C5A—C4A—H4A | 120.0 | H02B—C021—H02C | 109.5 |
C3—C2—C1 | 119.9 (3) | O10—C21—H21A | 109.5 |
C3—C2—H2 | 120.0 | O10—C21—H21B | 109.5 |
C1—C2—H2 | 120.0 | H21A—C21—H21B | 109.5 |
C1T—C2T—H2TA | 109.5 | O10—C21—H21C | 109.5 |
C1T—C2T—H2TB | 109.5 | H21A—C21—H21C | 109.5 |
H2TA—C2T—H2TB | 109.5 | H21B—C21—H21C | 109.5 |
C1T—C2T—H2TC | 109.5 | O9—C22—H22A | 109.5 |
H2TA—C2T—H2TC | 109.5 | O9—C22—H22B | 109.5 |
H2TB—C2T—H2TC | 109.5 | H22A—C22—H22B | 109.5 |
C2—C3—C4 | 120.6 (3) | O9—C22—H22C | 109.5 |
C2—C3—H3 | 119.7 | H22A—C22—H22C | 109.5 |
C4—C3—H3 | 119.7 | H22B—C22—H22C | 109.5 |
C4A—C3A—C2A | 120.0 (3) | O3—C022—H02D | 109.5 |
C4A—C3A—H3A | 120.0 | O3—C022—H02E | 109.5 |
C2A—C3A—H3A | 120.0 | H02D—C022—H02E | 109.5 |
C5—C4—C3 | 120.0 (3) | O3—C022—H02F | 109.5 |
C5—C4—H4 | 120.0 | H02D—C022—H02F | 109.5 |
C3—C4—H4 | 120.0 | H02E—C022—H02F | 109.5 |
C1A—C2A—C3A | 121.0 (3) | C19A—N01—C20A | 122.2 (2) |
C1A—C2A—H2A | 119.5 | C19A—N01—Al1 | 124.05 (18) |
C3A—C2A—H2A | 119.5 | C20A—N01—Al1 | 113.73 (17) |
C2A—C1A—C20A | 119.3 (3) | C6A—N02—C5A | 121.5 (2) |
C2A—C1A—H1A | 120.3 | C6A—N02—Al1 | 124.28 (18) |
C20A—C1A—H1A | 120.3 | C5A—N02—Al1 | 113.89 (17) |
C4—C5—C6 | 120.0 (3) | C20—N03—C1 | 121.2 (2) |
C4—C5—H5 | 120.0 | C20—N03—Al2 | 124.53 (19) |
C6—C5—H5 | 120.0 | C1—N03—Al2 | 114.18 (18) |
C5A—C20A—C1A | 119.5 (3) | C7—N04—C6 | 121.2 (2) |
C5A—C20A—N01 | 114.8 (2) | C7—N04—Al2 | 124.68 (19) |
C1A—C20A—N01 | 125.7 (3) | C6—N04—Al2 | 113.82 (18) |
C5—C6—C1 | 120.0 (3) | O18—N07—O17 | 120.7 (2) |
C5—C6—N04 | 125.0 (3) | O18—N07—O16 | 120.7 (2) |
C1—C6—N04 | 115.0 (2) | O17—N07—O16 | 118.6 (2) |
N04—C7—C8 | 125.1 (2) | O13—N08—O14 | 121.5 (3) |
N04—C7—H7 | 117.4 | O13—N08—O15 | 118.1 (3) |
C8—C7—H7 | 117.4 | O14—N08—O15 | 120.4 (3) |
N01—C19A—C18A | 124.6 (2) | C12A—O1—Al1 | 128.82 (16) |
N01—C19A—H19A | 117.7 | C1T—O1A—H1AA | 109.5 |
C18A—C19A—H19A | 117.7 | C13A—O2—Al1 | 129.86 (16) |
C13A—C18A—C17A | 119.5 (3) | C14A—O3—C022 | 117.7 (2) |
C13A—C18A—C19A | 123.0 (2) | C11A—O4—C021 | 116.4 (2) |
C17A—C18A—C19A | 117.4 (2) | Al1—O5—H52 | 121 (2) |
C13—C8—C9 | 119.2 (3) | Al1—O5—H51 | 126 (3) |
C13—C8—C7 | 122.7 (3) | H52—O5—H51 | 109 (4) |
C9—C8—C7 | 118.0 (2) | Al1—O6—H61 | 110 (3) |
C16A—C17A—C18A | 120.8 (3) | Al1—O6—H62 | 111 (2) |
C16A—C17A—H17A | 119.6 | H61—O6—H62 | 108 (3) |
C18A—C17A—H17A | 119.6 | C13—O7—Al2 | 130.62 (17) |
C10—C9—C8 | 121.2 (3) | C14—O8—Al2 | 130.45 (17) |
C10—C9—H9 | 119.4 | C15—O9—C22 | 117.1 (2) |
C8—C9—H9 | 119.4 | C12—O10—C21 | 117.0 (2) |
C17A—C16A—C15A | 120.3 (3) | Al2—O11—H11B | 124 (3) |
C17A—C16A—H16A | 119.9 | Al2—O11—H11A | 125 (3) |
C15A—C16A—H16A | 119.9 | H11B—O11—H11A | 111 (4) |
C9—C10—C11 | 119.7 (3) | Al2—O12—H12B | 112 (2) |
C9—C10—H10 | 120.2 | Al2—O12—H12A | 116 (3) |
C11—C10—H10 | 120.2 | H12B—O12—H12A | 106 (4) |
C12—C11—C10 | 120.3 (3) | O2—Al1—O1 | 93.64 (8) |
C12—C11—H11 | 119.8 | O2—Al1—O5 | 91.91 (9) |
C10—C11—H11 | 119.8 | O1—Al1—O5 | 93.74 (9) |
C14A—C15A—C16A | 120.2 (3) | O2—Al1—O6 | 90.49 (9) |
C14A—C15A—H15A | 119.9 | O1—Al1—O6 | 90.72 (8) |
C16A—C15A—H15A | 119.9 | O5—Al1—O6 | 174.80 (9) |
O3—C14A—C15A | 125.2 (3) | O2—Al1—N02 | 174.22 (9) |
O3—C14A—C13A | 114.0 (2) | O1—Al1—N02 | 92.09 (9) |
C15A—C14A—C13A | 120.7 (2) | O5—Al1—N02 | 88.49 (10) |
C11—C12—O10 | 125.3 (3) | O6—Al1—N02 | 88.67 (9) |
C11—C12—C13 | 120.9 (3) | O2—Al1—N01 | 93.08 (9) |
O10—C12—C13 | 113.8 (2) | O1—Al1—N01 | 172.56 (10) |
O2—C13A—C18A | 124.0 (2) | O5—Al1—N01 | 89.23 (9) |
O2—C13A—C14A | 117.5 (2) | O6—Al1—N01 | 86.03 (8) |
C18A—C13A—C14A | 118.4 (2) | N02—Al1—N01 | 81.16 (9) |
O7—C13—C8 | 123.8 (2) | O8—Al2—O7 | 92.64 (9) |
O7—C13—C12 | 117.5 (2) | O8—Al2—O11 | 93.25 (9) |
C8—C13—C12 | 118.6 (2) | O7—Al2—O11 | 90.98 (10) |
O8—C14—C19 | 123.9 (2) | O8—Al2—O12 | 90.12 (9) |
O8—C14—C15 | 118.0 (2) | O7—Al2—O12 | 92.38 (9) |
C19—C14—C15 | 118.2 (2) | O11—Al2—O12 | 175.12 (10) |
O1—C12A—C7A | 123.9 (2) | O8—Al2—N03 | 93.18 (9) |
O1—C12A—C11A | 118.2 (2) | O7—Al2—N03 | 173.99 (9) |
C7A—C12A—C11A | 117.9 (2) | O11—Al2—N03 | 87.18 (10) |
O4—C11A—C10A | 125.1 (2) | O12—Al2—N03 | 89.12 (10) |
O4—C11A—C12A | 113.7 (2) | O8—Al2—N04 | 173.64 (10) |
C10A—C11A—C12A | 121.2 (3) | O7—Al2—N04 | 92.57 (9) |
O9—C15—C16 | 125.2 (2) | O11—Al2—N04 | 90.32 (10) |
O9—C15—C14 | 113.5 (2) | O12—Al2—N04 | 86.01 (9) |
C16—C15—C14 | 121.2 (3) | N03—Al2—N04 | 81.73 (9) |
C11A—C10A—C9A | 119.8 (3) | C4T—C4R—H4R1 | 109.5 |
C11A—C10A—H10A | 120.1 | C4T—C4R—H4R2 | 109.5 |
C9A—C10A—H10A | 120.1 | H4R1—C4R—H4R2 | 109.5 |
C15—C16—C17 | 119.9 (3) | C4T—C4R—H4R3 | 109.5 |
C15—C16—H16 | 120.0 | H4R1—C4R—H4R3 | 109.5 |
C17—C16—H16 | 120.0 | H4R2—C4R—H4R3 | 109.5 |
C8A—C9A—C10A | 120.6 (3) | C4T—O4T—H4T | 109.5 |
C8A—C9A—H9A | 119.7 | C4R—C4T—O4T | 112.5 (6) |
C10A—C9A—H9A | 119.7 | C4R—C4T—H4T1 | 109.1 |
C18—C17—C16 | 120.3 (3) | O4T—C4T—H4T1 | 109.1 |
C18—C17—H17 | 119.8 | C4R—C4T—H4T2 | 109.1 |
C16—C17—H17 | 119.8 | O4T—C4T—H4T2 | 109.1 |
C9A—C8A—C7A | 120.2 (3) | H4T1—C4T—H4T2 | 107.8 |
C9A—C8A—H8A | 119.9 | C4U—O4U—H4U | 104.5 |
C7A—C8A—H8A | 119.9 | O4U—C4U—C4R | 117.6 (7) |
C17—C18—C19 | 120.9 (3) | O4U—C4U—H4U1 | 107.9 |
C17—C18—H18 | 119.6 | C4R—C4U—H4U1 | 107.9 |
C19—C18—H18 | 119.6 | O4U—C4U—H4U2 | 107.9 |
C12A—C7A—C8A | 120.0 (2) | C4R—C4U—H4U2 | 107.9 |
C12A—C7A—C6A | 122.3 (2) | H4U1—C4U—H4U2 | 107.2 |
C8A—C7A—C6A | 117.7 (3) | | |
| | | |
C20A—C5A—C4A—C3A | −1.1 (4) | O1—C12A—C7A—C6A | 4.1 (4) |
N02—C5A—C4A—C3A | −179.3 (3) | C11A—C12A—C7A—C6A | −174.5 (2) |
C6—C1—C2—C3 | −2.3 (4) | C9A—C8A—C7A—C12A | 0.5 (5) |
N03—C1—C2—C3 | 177.5 (3) | C9A—C8A—C7A—C6A | 178.9 (3) |
C1—C2—C3—C4 | −0.9 (5) | C17—C18—C19—C14 | −0.3 (4) |
C5A—C4A—C3A—C2A | 0.2 (4) | C17—C18—C19—C20 | −178.5 (3) |
C2—C3—C4—C5 | 1.8 (5) | O8—C14—C19—C18 | −179.4 (2) |
C4A—C3A—C2A—C1A | 0.9 (5) | C15—C14—C19—C18 | 0.6 (4) |
C3A—C2A—C1A—C20A | −1.0 (4) | O8—C14—C19—C20 | −1.3 (4) |
C3—C4—C5—C6 | 0.4 (5) | C15—C14—C19—C20 | 178.7 (2) |
C4A—C5A—C20A—C1A | 1.0 (4) | C12A—C7A—C6A—N02 | −4.8 (4) |
N02—C5A—C20A—C1A | 179.3 (2) | C8A—C7A—C6A—N02 | 176.9 (3) |
C4A—C5A—C20A—N01 | −177.2 (2) | C18—C19—C20—N03 | 178.8 (3) |
N02—C5A—C20A—N01 | 1.1 (3) | C14—C19—C20—N03 | 0.6 (4) |
C2A—C1A—C20A—C5A | 0.0 (4) | C18A—C19A—N01—C20A | −175.4 (2) |
C2A—C1A—C20A—N01 | 178.1 (2) | C18A—C19A—N01—Al1 | 6.1 (3) |
C4—C5—C6—C1 | −3.6 (4) | C5A—C20A—N01—C19A | −171.3 (2) |
C4—C5—C6—N04 | 176.5 (3) | C1A—C20A—N01—C19A | 10.6 (4) |
C2—C1—C6—C5 | 4.5 (4) | C5A—C20A—N01—Al1 | 7.3 (3) |
N03—C1—C6—C5 | −175.3 (2) | C1A—C20A—N01—Al1 | −170.8 (2) |
C2—C1—C6—N04 | −175.6 (2) | C7A—C6A—N02—C5A | 176.4 (2) |
N03—C1—C6—N04 | 4.6 (3) | C7A—C6A—N02—Al1 | −10.2 (4) |
N01—C19A—C18A—C13A | 4.1 (4) | C4A—C5A—N02—C6A | −16.8 (4) |
N01—C19A—C18A—C17A | −179.3 (3) | C20A—C5A—N02—C6A | 164.9 (2) |
N04—C7—C8—C13 | 1.6 (4) | C4A—C5A—N02—Al1 | 169.2 (2) |
N04—C7—C8—C9 | −177.5 (3) | C20A—C5A—N02—Al1 | −9.1 (3) |
C13A—C18A—C17A—C16A | 0.4 (4) | C19—C20—N03—C1 | −178.6 (2) |
C19A—C18A—C17A—C16A | −176.2 (3) | C19—C20—N03—Al2 | 4.2 (4) |
C13—C8—C9—C10 | 0.3 (4) | C2—C1—N03—C20 | 0.2 (4) |
C7—C8—C9—C10 | 179.4 (3) | C6—C1—N03—C20 | 180.0 (2) |
C18A—C17A—C16A—C15A | 1.8 (5) | C2—C1—N03—Al2 | 177.7 (2) |
C8—C9—C10—C11 | −0.4 (4) | C6—C1—N03—Al2 | −2.6 (3) |
C9—C10—C11—C12 | −0.1 (4) | C8—C7—N04—C6 | −179.3 (2) |
C17A—C16A—C15A—C14A | −1.2 (5) | C8—C7—N04—Al2 | −6.4 (4) |
C16A—C15A—C14A—O3 | 179.2 (3) | C5—C6—N04—C7 | −11.0 (4) |
C16A—C15A—C14A—C13A | −1.8 (4) | C1—C6—N04—C7 | 169.1 (2) |
C10—C11—C12—O10 | −179.2 (3) | C5—C6—N04—Al2 | 175.4 (2) |
C10—C11—C12—C13 | 0.9 (4) | C1—C6—N04—Al2 | −4.5 (3) |
C17A—C18A—C13A—O2 | 177.9 (2) | C7A—C12A—O1—Al1 | 13.5 (4) |
C19A—C18A—C13A—O2 | −5.7 (4) | C11A—C12A—O1—Al1 | −167.85 (18) |
C17A—C18A—C13A—C14A | −3.3 (4) | C18A—C13A—O2—Al1 | −4.5 (3) |
C19A—C18A—C13A—C14A | 173.2 (2) | C14A—C13A—O2—Al1 | 176.65 (17) |
O3—C14A—C13A—O2 | 2.1 (3) | C15A—C14A—O3—C022 | −2.1 (4) |
C15A—C14A—C13A—O2 | −177.1 (2) | C13A—C14A—O3—C022 | 178.7 (2) |
O3—C14A—C13A—C18A | −176.9 (2) | C10A—C11A—O4—C021 | 7.1 (4) |
C15A—C14A—C13A—C18A | 3.9 (4) | C12A—C11A—O4—C021 | −174.5 (2) |
C9—C8—C13—O7 | 179.7 (2) | C8—C13—O7—Al2 | 2.8 (4) |
C7—C8—C13—O7 | 0.7 (4) | C12—C13—O7—Al2 | −177.91 (18) |
C9—C8—C13—C12 | 0.5 (4) | C19—C14—O8—Al2 | −3.6 (4) |
C7—C8—C13—C12 | −178.6 (2) | C15—C14—O8—Al2 | 176.38 (17) |
C11—C12—C13—O7 | 179.6 (2) | C16—C15—O9—C22 | 13.3 (4) |
O10—C12—C13—O7 | −0.3 (3) | C14—C15—O9—C22 | −167.7 (2) |
C11—C12—C13—C8 | −1.1 (4) | C11—C12—O10—C21 | 0.1 (4) |
O10—C12—C13—C8 | 179.0 (2) | C13—C12—O10—C21 | 180.0 (2) |
O1—C12A—C11A—O4 | −2.5 (3) | C13A—O2—Al1—O1 | −172.4 (2) |
C7A—C12A—C11A—O4 | 176.2 (2) | C13A—O2—Al1—O5 | −78.5 (2) |
O1—C12A—C11A—C10A | 176.0 (2) | C13A—O2—Al1—O6 | 96.9 (2) |
C7A—C12A—C11A—C10A | −5.3 (4) | C13A—O2—Al1—N01 | 10.8 (2) |
O8—C14—C15—O9 | 0.3 (3) | C12A—O1—Al1—O2 | 159.5 (2) |
C19—C14—C15—O9 | −179.7 (2) | C12A—O1—Al1—O5 | 67.4 (2) |
O8—C14—C15—C16 | 179.3 (2) | C12A—O1—Al1—O6 | −109.9 (2) |
C19—C14—C15—C16 | −0.6 (4) | C12A—O1—Al1—N02 | −21.2 (2) |
O4—C11A—C10A—C9A | −179.2 (3) | C14—O8—Al2—O7 | −172.2 (2) |
C12A—C11A—C10A—C9A | 2.4 (5) | C14—O8—Al2—O11 | −81.1 (2) |
O9—C15—C16—C17 | 179.3 (2) | C14—O8—Al2—O12 | 95.4 (2) |
C14—C15—C16—C17 | 0.4 (4) | C14—O8—Al2—N03 | 6.3 (2) |
C11A—C10A—C9A—C8A | 2.1 (5) | C13—O7—Al2—O8 | 178.1 (2) |
C15—C16—C17—C18 | −0.1 (4) | C13—O7—Al2—O11 | 84.8 (2) |
C10A—C9A—C8A—C7A | −3.5 (5) | C13—O7—Al2—O12 | −91.7 (2) |
C16—C17—C18—C19 | 0.1 (4) | C13—O7—Al2—N04 | −5.6 (2) |
O1—C12A—C7A—C8A | −177.5 (3) | C4U—C4R—C4T—O4T | −171 (6) |
C11A—C12A—C7A—C8A | 3.8 (4) | C4T—C4R—C4U—O4U | 7 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H52···O16 | 0.87 (2) | 1.83 (3) | 2.684 (3) | 169 (3) |
O11—H11B···O1A | 0.85 (3) | 1.73 (3) | 2.573 (4) | 178 (7) |
Diaqua(6,6'-{(1
E,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·C2H6O | Z = 4 |
Mr = 588.21 | F(000) = 1216 |
Triclinic, P1 | Dx = 1.576 Mg m−3 |
a = 12.399 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.580 (5) Å | Cell parameters from 11972 reflections |
c = 16.419 (5) Å | θ = 1.0–1.0° |
α = 86.818 (5)° | µ = 1.17 mm−1 |
β = 78.871 (5)° | T = 100 K |
γ = 66.124 (5)° | Cuboid, yellow |
V = 2479.7 (16) Å3 | 0.57 × 0.24 × 0.23 mm |
Data collection top
Bruker APEXII CCD diffractometer | Rint = 0.027 |
φ and ω scans | θmax = 28.0°, θmin = 1.6° |
47407 measured reflections | h = −16→16 |
11972 independent reflections | k = −16→17 |
10426 reflections with I > 2σ(I) | l = −21→20 |
Refinement top
Refinement on F2 | 20 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.044 | H 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 reflections | Δρmax = 1.84 e Å−3 |
682 parameters | Δρmin = −2.07 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
Ga01 | 0.45155 (2) | 0.17569 (2) | 0.95269 (2) | 0.01661 (6) | |
Ga02 | 0.08156 (2) | 0.32174 (2) | 0.54724 (2) | 0.01661 (6) | |
O6 | 0.29643 (18) | −0.05042 (15) | 0.90092 (12) | 0.0244 (4) | |
N2A | 0.0987 (2) | 0.28745 (17) | 0.66651 (13) | 0.0206 (4) | |
C7A | −0.0959 (3) | 0.2234 (2) | 0.29245 (18) | 0.0292 (5) | |
H7A | −0.1286 | 0.1951 | 0.2584 | 0.035* | |
O4 | 0.39050 (16) | 0.08262 (14) | 0.91687 (10) | 0.0185 (3) | |
C15A | 0.2812 (2) | 0.4138 (2) | 0.72964 (17) | 0.0247 (5) | |
H15A | 0.2812 | 0.3858 | 0.7826 | 0.030* | |
C12A | 0.2796 (2) | 0.4998 (2) | 0.57193 (16) | 0.0224 (5) | |
O3 | 0.40813 (16) | 0.14689 (14) | 1.06566 (10) | 0.0187 (3) | |
O5 | 0.31225 (16) | 0.09519 (14) | 1.20518 (11) | 0.0213 (4) | |
C4 | 0.4966 (2) | 0.3212 (2) | 1.05411 (17) | 0.0225 (5) | |
H4 | 0.5227 | 0.3755 | 1.0593 | 0.027* | |
C21 | 0.2664 (3) | 0.0603 (2) | 1.28266 (17) | 0.0263 (6) | |
H21A | 0.2509 | −0.0015 | 1.2734 | 0.039* | |
H21B | 0.1932 | 0.1174 | 1.3084 | 0.039* | |
H21C | 0.3243 | 0.0417 | 1.3184 | 0.039* | |
C18 | 0.5848 (2) | 0.26915 (19) | 0.83385 (16) | 0.0199 (5) | |
O25 | 0.2711 (2) | 0.53867 (18) | 0.49337 (14) | 0.0349 (3) | |
O6A | 0.04001 (17) | 0.42112 (15) | 0.28984 (11) | 0.0231 (4) | |
O1 | 0.61681 (16) | 0.04865 (14) | 0.94634 (11) | 0.0188 (3) | |
C17 | 0.4886 (2) | 0.1814 (2) | 0.77038 (15) | 0.0210 (5) | |
H17 | 0.5152 | 0.2061 | 0.7198 | 0.025* | |
O16 | 0.32134 (19) | 0.49178 (16) | 0.92363 (15) | 0.0351 (5) | |
C22 | 0.2458 (3) | −0.1268 (2) | 0.8949 (2) | 0.0314 (6) | |
H22A | 0.2277 | −0.1531 | 0.9490 | 0.047* | |
H22B | 0.3023 | −0.1858 | 0.8588 | 0.047* | |
H22C | 0.1735 | −0.0927 | 0.8728 | 0.047* | |
O2A | −0.08101 (17) | 0.44875 (14) | 0.59385 (11) | 0.0209 (4) | |
C2A | −0.0556 (3) | 0.1040 (2) | 0.67441 (18) | 0.0274 (6) | |
H2AC | −0.0852 | 0.0755 | 0.6381 | 0.033* | |
O5A | 0.16622 (17) | 0.41135 (14) | 0.53847 (11) | 0.0216 (4) | |
C15 | 0.4045 (3) | 0.0944 (2) | 0.69046 (17) | 0.0293 (6) | |
H15 | 0.4309 | 0.1262 | 0.6437 | 0.035* | |
O4A | 0.04988 (17) | 0.35558 (14) | 0.43888 (11) | 0.0208 (4) | |
O10 | 0.3168 (2) | 0.84316 (16) | 0.42534 (14) | 0.0324 (4) | |
C22A | 0.3271 (3) | 0.6109 (3) | 0.4661 (2) | 0.0349 (3) | |
H22D | 0.3154 | 0.6327 | 0.4107 | 0.052* | |
H22E | 0.4115 | 0.5756 | 0.4666 | 0.052* | |
H22F | 0.2921 | 0.6732 | 0.5026 | 0.052* | |
C11A | 0.2196 (2) | 0.42986 (19) | 0.59469 (16) | 0.0198 (5) | |
O2 | 0.29328 (17) | 0.30294 (15) | 0.95132 (13) | 0.0265 (4) | |
O11 | 0.3445 (2) | 0.9705 (2) | 0.48120 (15) | 0.0409 (5) | |
C3A | −0.0052 (2) | 0.1777 (2) | 0.64648 (16) | 0.0217 (5) | |
O12 | 0.1678 (2) | 0.99308 (18) | 0.46706 (17) | 0.0440 (6) | |
C16 | 0.4232 (2) | 0.1152 (2) | 0.76905 (15) | 0.0210 (5) | |
C5A | −0.0401 (2) | 0.2303 (2) | 0.42517 (15) | 0.0196 (5) | |
C16A | 0.2210 (2) | 0.3868 (2) | 0.67492 (16) | 0.0214 (5) | |
O7 | 0.1295 (2) | 0.54519 (18) | 0.93591 (18) | 0.0443 (6) | |
C6A | −0.0894 (2) | 0.1882 (2) | 0.37179 (17) | 0.0245 (5) | |
H6A | −0.1178 | 0.1358 | 0.3910 | 0.029* | |
N1 | 0.52160 (19) | 0.27638 (16) | 0.98134 (13) | 0.0180 (4) | |
C14 | 0.3483 (3) | 0.0283 (3) | 0.68225 (18) | 0.0339 (7) | |
H14 | 0.3352 | 0.0168 | 0.6304 | 0.041* | |
C11 | 0.3817 (2) | 0.06723 (19) | 0.84022 (15) | 0.0181 (5) | |
N1A | 0.00006 (19) | 0.21935 (16) | 0.56512 (13) | 0.0197 (4) | |
N3 | 0.2764 (2) | 0.93433 (18) | 0.45785 (13) | 0.0235 (5) | |
C21A | 0.0575 (3) | 0.4449 (2) | 0.20350 (16) | 0.0287 (6) | |
H21D | 0.0885 | 0.4997 | 0.1953 | 0.043* | |
H21E | −0.0178 | 0.4699 | 0.1849 | 0.043* | |
H21F | 0.1135 | 0.3810 | 0.1723 | 0.043* | |
N4 | 0.2209 (2) | 0.56655 (18) | 0.92205 (16) | 0.0278 (5) | |
O9 | 0.2115 (2) | 0.65943 (17) | 0.90632 (17) | 0.0430 (6) | |
C4A | −0.0400 (2) | 0.1895 (2) | 0.50775 (16) | 0.0217 (5) | |
H4A | −0.0711 | 0.1376 | 0.5212 | 0.026* | |
N2 | 0.51356 (18) | 0.20938 (16) | 0.83601 (13) | 0.0177 (4) | |
C10A | 0.0034 (2) | 0.30990 (19) | 0.39546 (15) | 0.0181 (5) | |
C19 | 0.6505 (3) | 0.2923 (2) | 0.76180 (18) | 0.0270 (6) | |
H19 | 0.6480 | 0.2693 | 0.7101 | 0.032* | |
C18A | 0.0431 (2) | 0.2177 (2) | 0.70141 (16) | 0.0219 (5) | |
C12 | 0.3280 (2) | −0.0041 (2) | 0.82891 (16) | 0.0210 (5) | |
C13 | 0.3104 (3) | −0.0219 (2) | 0.75171 (18) | 0.0292 (6) | |
H13 | 0.2732 | −0.0676 | 0.7457 | 0.035* | |
C8 | 0.3146 (3) | 0.2457 (2) | 1.27768 (17) | 0.0310 (6) | |
H8 | 0.2764 | 0.2298 | 1.3280 | 0.037* | |
C10 | 0.3942 (2) | 0.20751 (19) | 1.12989 (15) | 0.0181 (5) | |
C5 | 0.4317 (2) | 0.2934 (2) | 1.12719 (16) | 0.0230 (5) | |
C9 | 0.3389 (2) | 0.1830 (2) | 1.20792 (16) | 0.0206 (5) | |
C8A | −0.0531 (2) | 0.3023 (2) | 0.26230 (16) | 0.0246 (5) | |
H8A | −0.0579 | 0.3263 | 0.2084 | 0.030* | |
C19A | 0.0328 (3) | 0.1886 (2) | 0.78431 (17) | 0.0280 (6) | |
H19A | 0.0609 | 0.2175 | 0.8215 | 0.034* | |
C1A | −0.0613 (3) | 0.0734 (2) | 0.75655 (19) | 0.0317 (6) | |
H1AA | −0.0936 | 0.0234 | 0.7750 | 0.038* | |
C9A | −0.0041 (2) | 0.3440 (2) | 0.31235 (15) | 0.0196 (5) | |
C17A | 0.1613 (2) | 0.3171 (2) | 0.70624 (16) | 0.0222 (5) | |
H17A | 0.1683 | 0.2914 | 0.7595 | 0.027* | |
C13A | 0.3384 (2) | 0.5236 (2) | 0.62578 (18) | 0.0264 (6) | |
H13A | 0.3781 | 0.5687 | 0.6093 | 0.032* | |
C14A | 0.3390 (3) | 0.4803 (2) | 0.70562 (18) | 0.0280 (6) | |
H14A | 0.3786 | 0.4969 | 0.7419 | 0.034* | |
C20A | −0.0192 (3) | 0.1167 (2) | 0.81145 (18) | 0.0315 (6) | |
H20A | −0.0259 | 0.0973 | 0.8668 | 0.038* | |
C3 | 0.5900 (2) | 0.30404 (19) | 0.91141 (16) | 0.0203 (5) | |
C2 | 0.6618 (3) | 0.3594 (2) | 0.91662 (19) | 0.0285 (6) | |
H2 | 0.6666 | 0.3810 | 0.9681 | 0.034* | |
C20 | 0.7193 (3) | 0.3496 (2) | 0.7677 (2) | 0.0325 (6) | |
H20 | 0.7615 | 0.3666 | 0.7197 | 0.039* | |
C1 | 0.7257 (3) | 0.3818 (3) | 0.8447 (2) | 0.0341 (7) | |
H1 | 0.7736 | 0.4188 | 0.8480 | 0.041* | |
C6 | 0.4077 (3) | 0.3553 (2) | 1.2003 (2) | 0.0354 (7) | |
H6 | 0.4333 | 0.4111 | 1.1988 | 0.042* | |
C7 | 0.3474 (3) | 0.3337 (3) | 1.2728 (2) | 0.0417 (8) | |
H7 | 0.3278 | 0.3776 | 1.3195 | 0.050* | |
C6B | 0.5687 (4) | 0.2399 (3) | 0.3791 (3) | 0.0535 (9) | |
H6BA | 0.5848 | 0.3000 | 0.3556 | 0.080* | |
H6BB | 0.5405 | 0.2110 | 0.3396 | 0.080* | |
H6BC | 0.6410 | 0.1853 | 0.3925 | 0.080* | |
C5B | 0.4736 (3) | 0.2769 (3) | 0.4573 (2) | 0.0349 (3) | |
H5BA | 0.5019 | 0.3074 | 0.4964 | 0.042* | |
H5BB | 0.4014 | 0.3332 | 0.4436 | 0.042* | |
C2B | 0.0900 (6) | 0.1407 (6) | 0.0735 (4) | 0.0292 (5) | 0.492 (6) |
H2BA | 0.1568 | 0.1376 | 0.0966 | 0.044* | 0.492 (6) |
H2BB | 0.1002 | 0.0689 | 0.0607 | 0.044* | 0.492 (6) |
H2BC | 0.0170 | 0.1746 | 0.1130 | 0.044* | 0.492 (6) |
O13 | 0.0912 (4) | 0.2902 (3) | 0.0223 (4) | 0.0324 (4) | 0.492 (6) |
H13B | 0.1064 | 0.2909 | 0.0686 | 0.049* | 0.492 (6) |
C4B | 0.0849 (8) | 0.1940 (6) | 0.0085 (5) | 0.0349 (3) | 0.492 (6) |
H4BA | 0.0103 | 0.2076 | −0.0097 | 0.042* | 0.492 (6) |
H4BB | 0.1508 | 0.1529 | −0.0351 | 0.042* | 0.492 (6) |
C3B | 0.0713 (5) | 0.1925 (5) | −0.0128 (4) | 0.0217 (5) | 0.508 (6) |
H3BA | 0.1363 | 0.1454 | −0.0542 | 0.026* | 0.508 (6) |
H3BB | −0.0019 | 0.2048 | −0.0326 | 0.026* | 0.508 (6) |
C1B | 0.0688 (9) | 0.1200 (7) | 0.0651 (6) | 0.0535 (9) | 0.508 (6) |
H1BA | 0.0606 | 0.0566 | 0.0495 | 0.080* | 0.508 (6) |
H1BB | 0.0020 | 0.1597 | 0.1077 | 0.080* | 0.508 (6) |
H1BC | 0.1421 | 0.0994 | 0.0857 | 0.080* | 0.508 (6) |
O15 | 0.0815 (5) | 0.2894 (4) | −0.0210 (4) | 0.0409 (5) | 0.508 (6) |
H15B | 0.0410 | 0.3283 | 0.0197 | 0.061* | 0.508 (6) |
O14 | 0.4471 (2) | 0.1992 (3) | 0.4926 (2) | 0.0653 (9) | |
H14B | 0.5091 | 0.1478 | 0.4985 | 0.098* | |
H1A | 0.614 (5) | −0.004 (3) | 0.922 (3) | 0.098* | |
H1B | 0.626 (5) | 0.033 (4) | 0.9960 (16) | 0.098* | |
H2A | 0.223 (3) | 0.304 (4) | 0.971 (4) | 0.098* | |
H2B | 0.289 (5) | 0.367 (2) | 0.952 (4) | 0.098* | |
H2AA | −0.070 (5) | 0.498 (3) | 0.613 (3) | 0.098* | |
H2AB | −0.122 (5) | 0.468 (4) | 0.556 (3) | 0.098* | |
O0AA | 0.23809 (18) | 0.19361 (15) | 0.50397 (13) | 0.0288 (4) | |
H0AA | 0.2378 | 0.1355 | 0.5278 | 0.043* | |
H0AB | 0.2974 | 0.2011 | 0.5188 | 0.043* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ga01 | 0.02039 (10) | 0.01428 (10) | 0.01347 (10) | −0.00593 (7) | −0.00250 (7) | 0.00317 (7) |
Ga02 | 0.02039 (10) | 0.01428 (10) | 0.01347 (10) | −0.00593 (7) | −0.00250 (7) | 0.00317 (7) |
O6 | 0.0307 (10) | 0.0245 (9) | 0.0236 (9) | −0.0170 (8) | −0.0055 (8) | 0.0036 (7) |
N2A | 0.0242 (11) | 0.0177 (10) | 0.0166 (10) | −0.0055 (8) | −0.0040 (8) | 0.0040 (8) |
C7A | 0.0301 (13) | 0.0338 (14) | 0.0239 (12) | −0.0119 (11) | −0.0061 (10) | −0.0046 (10) |
O4 | 0.0250 (9) | 0.0179 (8) | 0.0142 (8) | −0.0104 (7) | −0.0046 (7) | 0.0041 (6) |
C15A | 0.0257 (13) | 0.0247 (13) | 0.0198 (12) | −0.0056 (11) | −0.0060 (10) | 0.0026 (10) |
C12A | 0.0210 (12) | 0.0186 (12) | 0.0214 (12) | −0.0032 (10) | −0.0002 (9) | 0.0007 (9) |
O3 | 0.0258 (9) | 0.0160 (8) | 0.0140 (8) | −0.0096 (7) | −0.0004 (7) | 0.0015 (6) |
O5 | 0.0249 (9) | 0.0218 (9) | 0.0151 (8) | −0.0098 (7) | 0.0012 (7) | 0.0035 (7) |
C4 | 0.0256 (13) | 0.0138 (11) | 0.0274 (13) | −0.0075 (10) | −0.0044 (10) | 0.0012 (9) |
C21 | 0.0255 (13) | 0.0271 (13) | 0.0198 (12) | −0.0080 (11) | 0.0033 (10) | 0.0065 (10) |
C18 | 0.0194 (11) | 0.0144 (11) | 0.0225 (12) | −0.0052 (9) | −0.0012 (9) | 0.0068 (9) |
O25 | 0.0359 (8) | 0.0359 (8) | 0.0299 (8) | −0.0133 (7) | −0.0031 (6) | 0.0044 (6) |
O6A | 0.0306 (10) | 0.0239 (9) | 0.0153 (8) | −0.0117 (8) | −0.0042 (7) | 0.0029 (7) |
O1 | 0.0202 (8) | 0.0159 (8) | 0.0170 (8) | −0.0049 (7) | −0.0022 (7) | 0.0030 (6) |
C17 | 0.0214 (12) | 0.0198 (12) | 0.0155 (11) | −0.0036 (10) | −0.0013 (9) | 0.0065 (9) |
O16 | 0.0285 (11) | 0.0205 (10) | 0.0529 (14) | −0.0028 (8) | −0.0160 (10) | 0.0012 (9) |
C22 | 0.0360 (16) | 0.0267 (14) | 0.0392 (17) | −0.0183 (12) | −0.0135 (13) | 0.0051 (12) |
O2A | 0.0253 (9) | 0.0169 (8) | 0.0174 (9) | −0.0055 (7) | −0.0034 (7) | 0.0006 (7) |
C2A | 0.0365 (15) | 0.0216 (13) | 0.0245 (13) | −0.0122 (11) | −0.0072 (11) | 0.0051 (10) |
O5A | 0.0266 (9) | 0.0206 (9) | 0.0166 (8) | −0.0081 (7) | −0.0058 (7) | 0.0038 (7) |
C15 | 0.0347 (15) | 0.0346 (15) | 0.0170 (12) | −0.0117 (12) | −0.0079 (11) | 0.0058 (11) |
O4A | 0.0291 (10) | 0.0182 (8) | 0.0145 (8) | −0.0087 (7) | −0.0048 (7) | 0.0012 (6) |
O10 | 0.0352 (10) | 0.0208 (9) | 0.0377 (11) | −0.0085 (8) | −0.0035 (8) | −0.0055 (8) |
C22A | 0.0359 (8) | 0.0359 (8) | 0.0299 (8) | −0.0133 (7) | −0.0031 (6) | 0.0044 (6) |
C11A | 0.0184 (11) | 0.0165 (11) | 0.0191 (12) | −0.0025 (9) | −0.0010 (9) | −0.0001 (9) |
O2 | 0.0202 (9) | 0.0159 (8) | 0.0388 (11) | −0.0048 (7) | −0.0026 (8) | 0.0068 (8) |
O11 | 0.0513 (13) | 0.0439 (12) | 0.0392 (12) | −0.0288 (11) | −0.0124 (10) | −0.0003 (9) |
C3A | 0.0250 (13) | 0.0161 (11) | 0.0186 (12) | −0.0043 (10) | −0.0018 (9) | 0.0038 (9) |
O12 | 0.0339 (12) | 0.0271 (11) | 0.0552 (15) | 0.0013 (9) | −0.0029 (11) | −0.0004 (10) |
C16 | 0.0222 (12) | 0.0196 (12) | 0.0163 (11) | −0.0032 (10) | −0.0048 (9) | 0.0037 (9) |
C5A | 0.0174 (11) | 0.0174 (11) | 0.0184 (12) | −0.0024 (9) | −0.0002 (9) | −0.0011 (9) |
C16A | 0.0211 (12) | 0.0187 (11) | 0.0203 (12) | −0.0039 (10) | −0.0040 (9) | 0.0025 (9) |
O7 | 0.0298 (12) | 0.0285 (11) | 0.0762 (18) | −0.0123 (9) | −0.0111 (11) | −0.0031 (11) |
C6A | 0.0239 (13) | 0.0249 (13) | 0.0239 (13) | −0.0100 (11) | −0.0012 (10) | −0.0018 (10) |
N1 | 0.0192 (10) | 0.0142 (9) | 0.0199 (10) | −0.0068 (8) | −0.0031 (8) | 0.0042 (8) |
C14 | 0.0410 (17) | 0.0439 (17) | 0.0203 (13) | −0.0174 (14) | −0.0131 (12) | 0.0019 (12) |
C11 | 0.0176 (11) | 0.0162 (11) | 0.0166 (11) | −0.0025 (9) | −0.0047 (9) | 0.0020 (9) |
N1A | 0.0219 (10) | 0.0153 (9) | 0.0168 (10) | −0.0036 (8) | −0.0012 (8) | 0.0019 (8) |
N3 | 0.0350 (13) | 0.0196 (10) | 0.0160 (10) | −0.0122 (9) | −0.0036 (9) | 0.0042 (8) |
C21A | 0.0353 (15) | 0.0369 (15) | 0.0167 (12) | −0.0184 (13) | −0.0041 (11) | 0.0060 (11) |
N4 | 0.0312 (12) | 0.0172 (10) | 0.0353 (13) | −0.0069 (9) | −0.0136 (10) | 0.0012 (9) |
O9 | 0.0496 (14) | 0.0171 (10) | 0.0662 (17) | −0.0134 (10) | −0.0217 (12) | 0.0076 (10) |
C4A | 0.0210 (11) | 0.0203 (10) | 0.0191 (11) | −0.0044 (9) | −0.0017 (9) | −0.0001 (9) |
N2 | 0.0176 (10) | 0.0151 (9) | 0.0172 (10) | −0.0049 (8) | −0.0011 (8) | 0.0054 (7) |
C10A | 0.0168 (11) | 0.0154 (11) | 0.0160 (11) | −0.0010 (9) | −0.0006 (9) | −0.0023 (9) |
C19 | 0.0273 (14) | 0.0251 (13) | 0.0239 (13) | −0.0098 (11) | 0.0025 (11) | 0.0062 (10) |
C18A | 0.0245 (12) | 0.0177 (11) | 0.0196 (12) | −0.0054 (10) | −0.0032 (10) | 0.0049 (9) |
C12 | 0.0202 (12) | 0.0202 (12) | 0.0207 (12) | −0.0057 (10) | −0.0050 (9) | 0.0023 (9) |
C13 | 0.0301 (14) | 0.0345 (15) | 0.0272 (14) | −0.0150 (12) | −0.0098 (11) | −0.0012 (11) |
C8 | 0.0369 (16) | 0.0331 (15) | 0.0179 (13) | −0.0128 (13) | 0.0054 (11) | −0.0049 (11) |
C10 | 0.0187 (11) | 0.0142 (10) | 0.0157 (11) | −0.0019 (9) | −0.0008 (9) | 0.0007 (8) |
C5 | 0.0277 (13) | 0.0174 (11) | 0.0207 (12) | −0.0071 (10) | −0.0009 (10) | −0.0017 (9) |
C9 | 0.0199 (12) | 0.0192 (11) | 0.0177 (12) | −0.0040 (9) | −0.0008 (9) | 0.0001 (9) |
C8A | 0.0271 (13) | 0.0281 (13) | 0.0158 (12) | −0.0085 (11) | −0.0033 (10) | −0.0004 (10) |
C19A | 0.0354 (15) | 0.0293 (14) | 0.0195 (13) | −0.0131 (12) | −0.0072 (11) | 0.0062 (10) |
C1A | 0.0424 (17) | 0.0262 (14) | 0.0288 (15) | −0.0172 (13) | −0.0071 (12) | 0.0120 (11) |
C9A | 0.0196 (11) | 0.0187 (11) | 0.0160 (11) | −0.0042 (9) | −0.0008 (9) | −0.0005 (9) |
C17A | 0.0252 (13) | 0.0208 (12) | 0.0161 (11) | −0.0054 (10) | −0.0037 (9) | 0.0046 (9) |
C13A | 0.0230 (13) | 0.0244 (13) | 0.0291 (14) | −0.0082 (11) | −0.0018 (10) | 0.0012 (11) |
C14A | 0.0257 (14) | 0.0306 (14) | 0.0272 (14) | −0.0099 (11) | −0.0071 (11) | 0.0003 (11) |
C20A | 0.0431 (17) | 0.0305 (15) | 0.0202 (13) | −0.0151 (13) | −0.0075 (12) | 0.0121 (11) |
C3 | 0.0202 (12) | 0.0150 (11) | 0.0234 (12) | −0.0062 (9) | −0.0023 (9) | 0.0056 (9) |
C2 | 0.0300 (14) | 0.0283 (14) | 0.0313 (15) | −0.0169 (12) | −0.0048 (11) | 0.0043 (11) |
C20 | 0.0313 (15) | 0.0313 (15) | 0.0333 (16) | −0.0165 (12) | 0.0042 (12) | 0.0093 (12) |
C1 | 0.0322 (15) | 0.0346 (16) | 0.0412 (17) | −0.0225 (13) | −0.0016 (13) | 0.0076 (13) |
C6 | 0.0493 (19) | 0.0254 (14) | 0.0317 (16) | −0.0184 (14) | 0.0024 (13) | −0.0095 (12) |
C7 | 0.060 (2) | 0.0389 (18) | 0.0242 (15) | −0.0228 (16) | 0.0069 (14) | −0.0146 (13) |
C6B | 0.050 (2) | 0.047 (2) | 0.064 (2) | −0.0221 (16) | −0.0032 (17) | −0.0032 (17) |
C5B | 0.0359 (8) | 0.0359 (8) | 0.0299 (8) | −0.0133 (7) | −0.0031 (6) | 0.0044 (6) |
C2B | 0.0301 (13) | 0.0338 (14) | 0.0239 (12) | −0.0119 (11) | −0.0061 (10) | −0.0046 (10) |
O13 | 0.0352 (10) | 0.0208 (9) | 0.0377 (11) | −0.0085 (8) | −0.0035 (8) | −0.0055 (8) |
C4B | 0.0359 (8) | 0.0359 (8) | 0.0299 (8) | −0.0133 (7) | −0.0031 (6) | 0.0044 (6) |
C3B | 0.0210 (11) | 0.0203 (10) | 0.0191 (11) | −0.0044 (9) | −0.0017 (9) | −0.0001 (9) |
C1B | 0.050 (2) | 0.047 (2) | 0.064 (2) | −0.0221 (16) | −0.0032 (17) | −0.0032 (17) |
O15 | 0.0513 (13) | 0.0439 (12) | 0.0392 (12) | −0.0288 (11) | −0.0124 (10) | −0.0003 (9) |
O14 | 0.0270 (13) | 0.092 (2) | 0.0654 (19) | −0.0124 (14) | −0.0095 (13) | 0.0062 (17) |
O0AA | 0.0275 (10) | 0.0191 (9) | 0.0322 (11) | −0.0039 (8) | −0.0013 (8) | 0.0030 (8) |
Geometric parameters (Å, º) top
Ga01—O4 | 1.8829 (18) | C5A—C6A | 1.419 (4) |
Ga01—O3 | 1.8941 (18) | C5A—C4A | 1.436 (3) |
Ga01—N1 | 2.009 (2) | C16A—C17A | 1.441 (4) |
Ga01—N2 | 2.022 (2) | O7—N4 | 1.257 (3) |
Ga01—O2 | 2.0262 (19) | C6A—H6A | 0.9300 |
Ga01—O1 | 2.0644 (19) | N1—C3 | 1.419 (3) |
Ga02—O5A | 1.887 (2) | C14—C13 | 1.397 (4) |
Ga02—O4A | 1.8878 (18) | C14—H14 | 0.9300 |
Ga02—N1A | 2.005 (2) | C11—C12 | 1.417 (4) |
Ga02—N2A | 2.019 (2) | N1A—C4A | 1.298 (3) |
Ga02—O0AA | 2.042 (2) | C21A—H21D | 0.9600 |
Ga02—O2A | 2.0881 (19) | C21A—H21E | 0.9600 |
O6—C12 | 1.373 (3) | C21A—H21F | 0.9600 |
O6—C22 | 1.428 (3) | N4—O9 | 1.236 (3) |
N2A—C17A | 1.291 (4) | C4A—H4A | 0.9300 |
N2A—C18A | 1.420 (3) | C10A—C9A | 1.425 (3) |
C7A—C6A | 1.368 (4) | C19—C20 | 1.386 (4) |
C7A—C8A | 1.405 (4) | C19—H19 | 0.9300 |
C7A—H7A | 0.9300 | C18A—C19A | 1.393 (4) |
O4—C11 | 1.319 (3) | C12—C13 | 1.376 (4) |
C15A—C14A | 1.363 (4) | C13—H13 | 0.9300 |
C15A—C16A | 1.419 (4) | C8—C9 | 1.377 (4) |
C15A—H15A | 0.9300 | C8—C7 | 1.403 (5) |
C12A—O25 | 1.373 (3) | C8—H8 | 0.9300 |
C12A—C13A | 1.375 (4) | C10—C5 | 1.415 (4) |
C12A—C11A | 1.421 (4) | C10—C9 | 1.422 (3) |
O3—C10 | 1.315 (3) | C5—C6 | 1.417 (4) |
O5—C9 | 1.365 (3) | C8A—C9A | 1.374 (4) |
O5—C21 | 1.427 (3) | C8A—H8A | 0.9300 |
C4—N1 | 1.296 (3) | C19A—C20A | 1.386 (4) |
C4—C5 | 1.433 (4) | C19A—H19A | 0.9300 |
C4—H4 | 0.9300 | C1A—C20A | 1.385 (4) |
C21—H21A | 0.9600 | C1A—H1AA | 0.9300 |
C21—H21B | 0.9600 | C17A—H17A | 0.9300 |
C21—H21C | 0.9600 | C13A—C14A | 1.407 (4) |
C18—C19 | 1.398 (3) | C13A—H13A | 0.9300 |
C18—C3 | 1.405 (4) | C14A—H14A | 0.9300 |
C18—N2 | 1.417 (3) | C20A—H20A | 0.9300 |
O25—C22A | 1.424 (4) | C3—C2 | 1.393 (4) |
O6A—C9A | 1.369 (3) | C2—C1 | 1.382 (4) |
O6A—C21A | 1.431 (3) | C2—H2 | 0.9300 |
O1—H1A | 0.854 (19) | C20—C1 | 1.388 (5) |
O1—H1B | 0.850 (19) | C20—H20 | 0.9300 |
C17—N2 | 1.293 (3) | C1—H1 | 0.9300 |
C17—C16 | 1.437 (4) | C6—C7 | 1.364 (5) |
C17—H17 | 0.9300 | C6—H6 | 0.9300 |
O16—N4 | 1.253 (3) | C7—H7 | 0.9300 |
C22—H22A | 0.9600 | C6B—C5B | 1.517 (5) |
C22—H22B | 0.9600 | C6B—H6BA | 0.9600 |
C22—H22C | 0.9600 | C6B—H6BB | 0.9600 |
O2A—H2AA | 0.832 (19) | C6B—H6BC | 0.9600 |
O2A—H2AB | 0.838 (19) | C5B—O14 | 1.302 (5) |
C2A—C1A | 1.386 (4) | C5B—H5BA | 0.9700 |
C2A—C3A | 1.395 (4) | C5B—H5BB | 0.9700 |
C2A—H2AC | 0.9300 | C2B—C4B | 1.252 (10) |
O5A—C11A | 1.323 (3) | C2B—H2BA | 0.9600 |
C15—C14 | 1.365 (4) | C2B—H2BB | 0.9600 |
C15—C16 | 1.417 (4) | C2B—H2BC | 0.9600 |
C15—H15 | 0.9300 | O13—C4B | 1.373 (8) |
O4A—C10A | 1.313 (3) | O13—H13B | 0.8200 |
O10—N3 | 1.240 (3) | C4B—H4BA | 0.9700 |
C22A—H22D | 0.9600 | C4B—H4BB | 0.9700 |
C22A—H22E | 0.9600 | C3B—O15 | 1.369 (7) |
C22A—H22F | 0.9600 | C3B—C1B | 1.575 (11) |
C11A—C16A | 1.412 (3) | C3B—H3BA | 0.9700 |
O2—H2A | 0.855 (19) | C3B—H3BB | 0.9700 |
O2—H2B | 0.854 (19) | C1B—H1BA | 0.9600 |
O11—N3 | 1.259 (3) | C1B—H1BB | 0.9600 |
C3A—C18A | 1.412 (4) | C1B—H1BC | 0.9600 |
C3A—N1A | 1.422 (3) | O15—H15B | 0.8200 |
O12—N3 | 1.240 (3) | O14—H14B | 0.8200 |
C16—C11 | 1.417 (3) | O0AA—H0AA | 0.8624 |
C5A—C10A | 1.418 (4) | O0AA—H0AB | 0.8623 |
| | | |
O4—Ga01—O3 | 91.95 (8) | O6A—C21A—H21E | 109.5 |
O4—Ga01—N1 | 175.43 (8) | H21D—C21A—H21E | 109.5 |
O3—Ga01—N1 | 92.60 (8) | O6A—C21A—H21F | 109.5 |
O4—Ga01—N2 | 93.84 (8) | H21D—C21A—H21F | 109.5 |
O3—Ga01—N2 | 173.36 (8) | H21E—C21A—H21F | 109.5 |
N1—Ga01—N2 | 81.59 (9) | O9—N4—O16 | 120.9 (3) |
O4—Ga01—O2 | 90.60 (9) | O9—N4—O7 | 120.4 (2) |
O3—Ga01—O2 | 93.72 (8) | O16—N4—O7 | 118.7 (2) |
N1—Ga01—O2 | 89.56 (9) | N1A—C4A—C5A | 125.2 (2) |
N2—Ga01—O2 | 89.48 (8) | N1A—C4A—H4A | 117.4 |
O4—Ga01—O1 | 89.74 (8) | C5A—C4A—H4A | 117.4 |
O3—Ga01—O1 | 90.02 (7) | C17—N2—C18 | 123.5 (2) |
N1—Ga01—O1 | 89.80 (8) | C17—N2—Ga01 | 123.54 (18) |
N2—Ga01—O1 | 86.76 (8) | C18—N2—Ga01 | 112.92 (16) |
O2—Ga01—O1 | 176.23 (8) | O4A—C10A—C5A | 125.0 (2) |
O5A—Ga02—O4A | 91.11 (8) | O4A—C10A—C9A | 117.0 (2) |
O5A—Ga02—N1A | 174.56 (8) | C5A—C10A—C9A | 118.0 (2) |
O4A—Ga02—N1A | 93.96 (8) | C20—C19—C18 | 119.7 (3) |
O5A—Ga02—N2A | 92.88 (8) | C20—C19—H19 | 120.1 |
O4A—Ga02—N2A | 174.46 (9) | C18—C19—H19 | 120.1 |
N1A—Ga02—N2A | 82.20 (9) | C19A—C18A—C3A | 119.5 (2) |
O5A—Ga02—O0AA | 89.90 (9) | C19A—C18A—N2A | 124.5 (3) |
O4A—Ga02—O0AA | 91.77 (8) | C3A—C18A—N2A | 115.9 (2) |
N1A—Ga02—O0AA | 87.98 (9) | O6—C12—C13 | 125.4 (2) |
N2A—Ga02—O0AA | 92.08 (9) | O6—C12—C11 | 113.6 (2) |
O5A—Ga02—O2A | 92.01 (8) | C13—C12—C11 | 121.0 (2) |
O4A—Ga02—O2A | 89.17 (8) | C12—C13—C14 | 120.4 (3) |
N1A—Ga02—O2A | 90.03 (9) | C12—C13—H13 | 119.8 |
N2A—Ga02—O2A | 86.84 (8) | C14—C13—H13 | 119.8 |
O0AA—Ga02—O2A | 177.85 (8) | C9—C8—C7 | 120.0 (3) |
C12—O6—C22 | 117.4 (2) | C9—C8—H8 | 120.0 |
C17A—N2A—C18A | 122.1 (2) | C7—C8—H8 | 120.0 |
C17A—N2A—Ga02 | 124.87 (18) | O3—C10—C5 | 125.0 (2) |
C18A—N2A—Ga02 | 112.76 (17) | O3—C10—C9 | 116.9 (2) |
C6A—C7A—C8A | 120.2 (3) | C5—C10—C9 | 118.0 (2) |
C6A—C7A—H7A | 119.9 | C10—C5—C6 | 119.7 (2) |
C8A—C7A—H7A | 119.9 | C10—C5—C4 | 123.7 (2) |
C11—O4—Ga01 | 127.10 (16) | C6—C5—C4 | 116.5 (2) |
C14A—C15A—C16A | 120.9 (3) | O5—C9—C8 | 125.3 (2) |
C14A—C15A—H15A | 119.5 | O5—C9—C10 | 113.8 (2) |
C16A—C15A—H15A | 119.5 | C8—C9—C10 | 121.0 (2) |
O25—C12A—C13A | 125.7 (3) | C9A—C8A—C7A | 120.0 (2) |
O25—C12A—C11A | 113.2 (2) | C9A—C8A—H8A | 120.0 |
C13A—C12A—C11A | 121.2 (2) | C7A—C8A—H8A | 120.0 |
C10—O3—Ga01 | 126.03 (15) | C20A—C19A—C18A | 120.0 (3) |
C9—O5—C21 | 116.6 (2) | C20A—C19A—H19A | 120.0 |
N1—C4—C5 | 124.8 (2) | C18A—C19A—H19A | 120.0 |
N1—C4—H4 | 117.6 | C20A—C1A—C2A | 120.6 (3) |
C5—C4—H4 | 117.6 | C20A—C1A—H1AA | 119.7 |
O5—C21—H21A | 109.5 | C2A—C1A—H1AA | 119.7 |
O5—C21—H21B | 109.5 | O6A—C9A—C8A | 125.2 (2) |
H21A—C21—H21B | 109.5 | O6A—C9A—C10A | 113.4 (2) |
O5—C21—H21C | 109.5 | C8A—C9A—C10A | 121.4 (2) |
H21A—C21—H21C | 109.5 | N2A—C17A—C16A | 125.4 (2) |
H21B—C21—H21C | 109.5 | N2A—C17A—H17A | 117.3 |
C19—C18—C3 | 119.4 (2) | C16A—C17A—H17A | 117.3 |
C19—C18—N2 | 125.0 (2) | C12A—C13A—C14A | 120.5 (3) |
C3—C18—N2 | 115.6 (2) | C12A—C13A—H13A | 119.8 |
C12A—O25—C22A | 116.8 (2) | C14A—C13A—H13A | 119.8 |
C9A—O6A—C21A | 117.0 (2) | C15A—C14A—C13A | 119.7 (3) |
Ga01—O1—H1A | 107 (4) | C15A—C14A—H14A | 120.1 |
Ga01—O1—H1B | 107 (4) | C13A—C14A—H14A | 120.1 |
H1A—O1—H1B | 110 (3) | C1A—C20A—C19A | 120.4 (3) |
N2—C17—C16 | 125.5 (2) | C1A—C20A—H20A | 119.8 |
N2—C17—H17 | 117.3 | C19A—C20A—H20A | 119.8 |
C16—C17—H17 | 117.3 | C2—C3—C18 | 120.3 (2) |
O6—C22—H22A | 109.5 | C2—C3—N1 | 123.9 (2) |
O6—C22—H22B | 109.5 | C18—C3—N1 | 115.8 (2) |
H22A—C22—H22B | 109.5 | C1—C2—C3 | 119.5 (3) |
O6—C22—H22C | 109.5 | C1—C2—H2 | 120.3 |
H22A—C22—H22C | 109.5 | C3—C2—H2 | 120.3 |
H22B—C22—H22C | 109.5 | C19—C20—C1 | 120.4 (3) |
Ga02—O2A—H2AA | 111 (4) | C19—C20—H20 | 119.8 |
Ga02—O2A—H2AB | 109 (4) | C1—C20—H20 | 119.8 |
H2AA—O2A—H2AB | 113 (3) | C2—C1—C20 | 120.7 (3) |
C1A—C2A—C3A | 119.7 (3) | C2—C1—H1 | 119.6 |
C1A—C2A—H2AC | 120.2 | C20—C1—H1 | 119.6 |
C3A—C2A—H2AC | 120.2 | C7—C6—C5 | 120.4 (3) |
C11A—O5A—Ga02 | 127.81 (16) | C7—C6—H6 | 119.8 |
C14—C15—C16 | 121.1 (3) | C5—C6—H6 | 119.8 |
C14—C15—H15 | 119.4 | C6—C7—C8 | 120.6 (3) |
C16—C15—H15 | 119.4 | C6—C7—H7 | 119.7 |
C10A—O4A—Ga02 | 127.15 (16) | C8—C7—H7 | 119.7 |
O25—C22A—H22D | 109.5 | C5B—C6B—H6BA | 109.5 |
O25—C22A—H22E | 109.5 | C5B—C6B—H6BB | 109.5 |
H22D—C22A—H22E | 109.5 | H6BA—C6B—H6BB | 109.5 |
O25—C22A—H22F | 109.5 | C5B—C6B—H6BC | 109.5 |
H22D—C22A—H22F | 109.5 | H6BA—C6B—H6BC | 109.5 |
H22E—C22A—H22F | 109.5 | H6BB—C6B—H6BC | 109.5 |
O5A—C11A—C16A | 125.6 (2) | O14—C5B—C6B | 112.8 (3) |
O5A—C11A—C12A | 116.7 (2) | O14—C5B—H5BA | 109.0 |
C16A—C11A—C12A | 117.8 (2) | C6B—C5B—H5BA | 109.0 |
Ga01—O2—H2A | 126 (3) | O14—C5B—H5BB | 109.0 |
Ga01—O2—H2B | 121 (3) | C6B—C5B—H5BB | 109.0 |
H2A—O2—H2B | 108 (3) | H5BA—C5B—H5BB | 107.8 |
C2A—C3A—C18A | 119.7 (2) | C4B—C2B—H2BA | 109.5 |
C2A—C3A—N1A | 124.9 (3) | C4B—C2B—H2BB | 109.5 |
C18A—C3A—N1A | 115.4 (2) | H2BA—C2B—H2BB | 109.5 |
C15—C16—C11 | 119.2 (3) | C4B—C2B—H2BC | 109.5 |
C15—C16—C17 | 116.7 (2) | H2BA—C2B—H2BC | 109.5 |
C11—C16—C17 | 124.0 (2) | H2BB—C2B—H2BC | 109.5 |
C10A—C5A—C6A | 119.3 (2) | C4B—O13—H13B | 109.5 |
C10A—C5A—C4A | 124.1 (2) | C2B—C4B—O13 | 110.5 (6) |
C6A—C5A—C4A | 116.6 (2) | C2B—C4B—H4BA | 109.5 |
C11A—C16A—C15A | 119.9 (2) | O13—C4B—H4BA | 109.5 |
C11A—C16A—C17A | 123.2 (2) | C2B—C4B—H4BB | 109.5 |
C15A—C16A—C17A | 116.9 (2) | O13—C4B—H4BB | 109.5 |
C7A—C6A—C5A | 121.1 (3) | H4BA—C4B—H4BB | 108.1 |
C7A—C6A—H6A | 119.5 | O15—C3B—C1B | 130.8 (6) |
C5A—C6A—H6A | 119.5 | O15—C3B—H3BA | 104.6 |
C4—N1—C3 | 122.7 (2) | C1B—C3B—H3BA | 104.6 |
C4—N1—Ga01 | 123.77 (18) | O15—C3B—H3BB | 104.6 |
C3—N1—Ga01 | 113.12 (17) | C1B—C3B—H3BB | 104.6 |
C15—C14—C13 | 120.0 (3) | H3BA—C3B—H3BB | 105.7 |
C15—C14—H14 | 120.0 | C3B—C1B—H1BA | 109.5 |
C13—C14—H14 | 120.0 | C3B—C1B—H1BB | 109.5 |
O4—C11—C12 | 116.8 (2) | H1BA—C1B—H1BB | 109.5 |
O4—C11—C16 | 125.0 (2) | C3B—C1B—H1BC | 109.5 |
C12—C11—C16 | 118.1 (2) | H1BA—C1B—H1BC | 109.5 |
C4A—N1A—C3A | 122.4 (2) | H1BB—C1B—H1BC | 109.5 |
C4A—N1A—Ga02 | 124.02 (18) | C3B—O15—H15B | 109.5 |
C3A—N1A—Ga02 | 113.50 (17) | C5B—O14—H14B | 109.5 |
O12—N3—O10 | 120.8 (3) | Ga02—O0AA—H0AA | 110.3 |
O12—N3—O11 | 118.1 (2) | Ga02—O0AA—H0AB | 110.0 |
O10—N3—O11 | 121.0 (3) | H0AA—O0AA—H0AB | 103.7 |
O6A—C21A—H21D | 109.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···O4i | 0.85 (2) | 2.11 (4) | 2.800 (2) | 138 (4) |
O1—H1A···O3i | 0.85 (2) | 2.06 (3) | 2.816 (3) | 147 (5) |
O2A—H2AB···O5Aii | 0.84 (2) | 2.17 (4) | 2.872 (3) | 141 (5) |
O2A—H2AA···O4Aii | 0.83 (2) | 2.20 (4) | 2.844 (3) | 134 (5) |
O2—H2B···O16 | 0.85 (2) | 1.90 (2) | 2.727 (3) | 161 (5) |
O2—H2A···O13iii | 0.86 (2) | 1.77 (2) | 2.620 (5) | 170 (6) |
O2—H2A···O15iii | 0.86 (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 topComplex 1 | | | | |
O5—H52···O16 | 0.87 (2) | 1.83 (3) | 2.684 (3) | 169 (3) |
O11—H11B···O1A | 0.83 (3) | 1.73 (3) | 2.573 (4) | 178 (7) |
| | | | |
Complex 2 | | | | |
O2—H2B···O7 | 0.85 (3) | 2.47 (4) | 3.116 (3) | 134 (5) |
O2—H2B···O16 | 0.85 (3) | 1.91 (4) | 2.727 (3) | 161 (6) |
Geometrical parameters (Å, °) for π–π stacking for 1 and
2 topComplex | Cgia | [Res]-Cgjb | Rcc | R1vd | R2ve | Af | Bg | Γh |
1 | Cg5 | [2]⋯Cg6iii | 3.654 (3) | -3.3184 (10) | -3.3995 (12) | 7.61 (15) | 24.73 | 21.49 |
| | | | | | | | |
2 | Cg1 | [2]⋯Cg2i | 3.972 (5) | 3.7819 (11) | 3.1648 (11) | 19.59 (18) | 17.81 | 37.18 |
| Cg3 | [2]⋯Cg4ii | 3.703 (4) | 3.4169 (13) | 3.3194 (18) | 7.64 (13) | 22.68 | 26.31 |
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 topComplex | X—H(I) | Res(I)→Cg(J) | H···Cg | X—H···Cg | Y···Cg |
1 | C021—H02Aii | [1] Cg2 | 2.86 (8) | 170 | 3.817 (3) |
2 | C21—H21Bi | [1] Cg11 | 2.80 (2) | 162 | 3.729 (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 topComplex | Bond | Bond length via XRD | Bond length via DFT | Angle | Bond angle via XRD | Bond angle via DFT |
Complex 1 | N01—Al1 | 2.007 (2) | 2.007 | O2—Al1—O1 | 93.64 (8) | 94.5 |
| N02—Al1 | 1.988 (2) | 1.987 | O2—Al1—N01 | 93.08 (9) | 92.8 |
| O1—Al1 | 1.8197 (19) | 1.820 | N02—Al1—N01 | 81.16 (9) | 81.6 |
| O2—Al1 | 1.8066 (19) | 1.807 | O1—Al1—N02 | 92.09 (9) | 91.6 |
Complex 2 | O5A—Ga02 | 1.887 (2) | 1.891 | O4A—Ga02—O5A | 91.11 (8) | 91.5 |
| O4A—Ga02 | 1.8878 (18) | 1.889 | O5A—Ga02—N2A | 92.88 (8) | 93.1 |
| N2A—Ga02 | 2.019 (2) | 2.022 | N2A—Ga02—N1A | 82.20 (9) | 81.9 |
| N1A—Ga02 | 2.005 (2) | 2.009 | N1A—Ga02—O4A | 93.96 (8) | 94.2 |