Acta Cryst. (2008). E64, m1509 [ doi:10.1107/S1600536808035460 ]
O)bis(2-methylquinolin-8-olato-
2N,O)titanium(IV)The two 2-methylquinolin-8-olate anions in the title complex, [Ti(C10H8NO)2(C3H7O)2], chelate the TiIV atom, which shows an all-cis distorted octahedral N2O4 coordination geometry.
8-Hydroxy-2-methylquinoline (1.59 g, 10 mmol) was added to the titanium isopropoxide (2.84 g, 10 mmol) in toluene (20 ml) at room temperature. The mixture was stirred for a day and than solvent was removed under reduced pressure to furnish an orange solid. The solid was crystallized from dichloromethane and n-hexane (1:1) to give yellow crystals, m.p. 445 K. IR (KBr, cm-1): 1575 (C═C, C═N), 1236 (C—O). 1H NMR (CDCl3, p.p.m.): 0.94 (CH3, doublet), 1.14 (CH3, doublet), 2.83 (CH3, singlet), 4.61 (CH, quartet), 6.9–8.58 (aromatic H atoms).
Hydrogen atoms were placed in their calculated positions (C—H 0.95–0.98 Å) and were treated as riding on their parent atoms, with U(H) set to 1.2–1.5 times Ueq(C).
Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).
| Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Ti(C10H8NO)2(C3H7O)2 at the 70% probability level showing atom labelling. Hydrogen atoms are drawn as spheres of arbitrary radius. |
| [Ti(C10H8NO)2(C3H7O)2] | F(000) = 1016 |
| Mr = 482.42 | Dx = 1.343 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 6457 reflections |
| a = 9.5851 (2) Å | θ = 2.2–28.3° |
| b = 13.5768 (2) Å | µ = 0.39 mm−1 |
| c = 18.7779 (3) Å | T = 100 K |
| β = 102.559 (1)° | Irregular chip, yellow |
| V = 2385.19 (7) Å3 | 0.35 × 0.25 × 0.15 mm |
| Z = 4 |
| Bruker SMART APEX diffractometer | 5467 independent reflections |
| Radiation source: fine-focus sealed tube | 4651 reflections with I > 2σ(I) |
| graphite | Rint = 0.025 |
| ω scans | θmax = 27.5°, θmin = 2.2° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→11 |
| Tmin = 0.875, Tmax = 0.943 | k = −17→17 |
| 16391 measured reflections | l = −24→24 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.088 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0394P)2 + 1.3426P] where P = (Fo2 + 2Fc2)/3 |
| 5467 reflections | (Δ/σ)max = 0.001 |
| 304 parameters | Δρmax = 0.39 e Å−3 |
| 0 restraints | Δρmin = −0.39 e Å−3 |
| [Ti(C10H8NO)2(C3H7O)2] | V = 2385.19 (7) Å3 |
| Mr = 482.42 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 9.5851 (2) Å | µ = 0.39 mm−1 |
| b = 13.5768 (2) Å | T = 100 K |
| c = 18.7779 (3) Å | 0.35 × 0.25 × 0.15 mm |
| β = 102.559 (1)° |
| Bruker SMART APEX diffractometer | 5467 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4651 reflections with I > 2σ(I) |
| Tmin = 0.875, Tmax = 0.943 | Rint = 0.025 |
| 16391 measured reflections | θmax = 27.5° |
| R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
| wR(F2) = 0.088 | Δρmax = 0.39 e Å−3 |
| S = 1.03 | Δρmin = −0.39 e Å−3 |
| 5467 reflections | Absolute structure: ? |
| 304 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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. |
| x | y | z | Uiso*/Ueq | ||
| Ti1 | 0.36712 (3) | 0.433571 (18) | 0.241664 (14) | 0.01288 (8) | |
| O1 | 0.26537 (11) | 0.55637 (7) | 0.23824 (6) | 0.0166 (2) | |
| O2 | 0.46090 (11) | 0.31617 (7) | 0.28355 (5) | 0.0153 (2) | |
| O3 | 0.49414 (11) | 0.48288 (8) | 0.19514 (6) | 0.0187 (2) | |
| O4 | 0.24248 (11) | 0.37144 (8) | 0.16802 (5) | 0.0171 (2) | |
| N1 | 0.19366 (13) | 0.41035 (9) | 0.31601 (6) | 0.0142 (2) | |
| N2 | 0.51257 (13) | 0.48222 (9) | 0.35581 (6) | 0.0145 (2) | |
| C1 | 0.16171 (16) | 0.57482 (11) | 0.27306 (8) | 0.0169 (3) | |
| C2 | 0.09311 (17) | 0.66473 (12) | 0.27024 (9) | 0.0219 (3) | |
| H2 | 0.1206 | 0.7172 | 0.2427 | 0.026* | |
| C3 | −0.01715 (18) | 0.67913 (12) | 0.30789 (9) | 0.0261 (4) | |
| H3 | −0.0628 | 0.7415 | 0.3055 | 0.031* | |
| C4 | −0.05984 (17) | 0.60535 (13) | 0.34771 (9) | 0.0259 (4) | |
| H4 | −0.1351 | 0.6164 | 0.3724 | 0.031* | |
| C5 | 0.00847 (16) | 0.51221 (12) | 0.35212 (8) | 0.0204 (3) | |
| C6 | 0.12004 (15) | 0.49752 (11) | 0.31484 (8) | 0.0155 (3) | |
| C7 | −0.02862 (17) | 0.43106 (13) | 0.39098 (9) | 0.0244 (3) | |
| H7 | −0.1022 | 0.4370 | 0.4174 | 0.029* | |
| C8 | 0.04179 (17) | 0.34421 (13) | 0.39039 (9) | 0.0228 (3) | |
| H8 | 0.0155 | 0.2890 | 0.4157 | 0.027* | |
| C9 | 0.15426 (16) | 0.33490 (11) | 0.35243 (8) | 0.0170 (3) | |
| C10 | 0.22910 (17) | 0.23783 (11) | 0.35446 (9) | 0.0210 (3) | |
| H10A | 0.2668 | 0.2303 | 0.3102 | 0.032* | |
| H10B | 0.1615 | 0.1845 | 0.3570 | 0.032* | |
| H10C | 0.3081 | 0.2352 | 0.3975 | 0.032* | |
| C11 | 0.54608 (15) | 0.31020 (11) | 0.34980 (8) | 0.0151 (3) | |
| C12 | 0.60985 (17) | 0.22382 (12) | 0.37911 (8) | 0.0197 (3) | |
| H12 | 0.5961 | 0.1647 | 0.3514 | 0.024* | |
| C13 | 0.69565 (17) | 0.22374 (12) | 0.45060 (9) | 0.0226 (3) | |
| H13 | 0.7381 | 0.1638 | 0.4706 | 0.027* | |
| C14 | 0.71930 (17) | 0.30763 (12) | 0.49184 (9) | 0.0215 (3) | |
| H14 | 0.7760 | 0.3054 | 0.5401 | 0.026* | |
| C15 | 0.65868 (16) | 0.39776 (12) | 0.46212 (8) | 0.0170 (3) | |
| C16 | 0.57156 (15) | 0.39851 (11) | 0.39100 (8) | 0.0145 (3) | |
| C17 | 0.68312 (16) | 0.49006 (12) | 0.49736 (8) | 0.0199 (3) | |
| H17 | 0.7367 | 0.4940 | 0.5462 | 0.024* | |
| C18 | 0.62969 (17) | 0.57309 (11) | 0.46108 (8) | 0.0197 (3) | |
| H18 | 0.6493 | 0.6353 | 0.4842 | 0.024* | |
| C19 | 0.54487 (16) | 0.56820 (11) | 0.38889 (8) | 0.0171 (3) | |
| C20 | 0.49429 (18) | 0.66222 (11) | 0.35024 (9) | 0.0235 (3) | |
| H20A | 0.4595 | 0.6491 | 0.2981 | 0.035* | |
| H20B | 0.5736 | 0.7093 | 0.3570 | 0.035* | |
| H20C | 0.4166 | 0.6899 | 0.3704 | 0.035* | |
| C21 | 0.63093 (17) | 0.48966 (12) | 0.17852 (9) | 0.0199 (3) | |
| H21 | 0.6754 | 0.5535 | 0.1980 | 0.024* | |
| C22 | 0.6130 (2) | 0.48986 (15) | 0.09632 (9) | 0.0321 (4) | |
| H22A | 0.5505 | 0.5445 | 0.0754 | 0.048* | |
| H22B | 0.5703 | 0.4274 | 0.0764 | 0.048* | |
| H22C | 0.7066 | 0.4978 | 0.0840 | 0.048* | |
| C23 | 0.72535 (18) | 0.40664 (13) | 0.21459 (10) | 0.0274 (4) | |
| H23A | 0.7328 | 0.4091 | 0.2674 | 0.041* | |
| H23B | 0.8207 | 0.4135 | 0.2042 | 0.041* | |
| H23C | 0.6838 | 0.3434 | 0.1956 | 0.041* | |
| C24 | 0.17566 (17) | 0.41249 (11) | 0.09929 (8) | 0.0181 (3) | |
| H24 | 0.2249 | 0.4755 | 0.0922 | 0.022* | |
| C25 | 0.1915 (2) | 0.34129 (13) | 0.03960 (9) | 0.0308 (4) | |
| H25A | 0.2932 | 0.3306 | 0.0411 | 0.046* | |
| H25B | 0.1451 | 0.3687 | −0.0079 | 0.046* | |
| H25C | 0.1464 | 0.2784 | 0.0470 | 0.046* | |
| C26 | 0.02027 (18) | 0.43437 (14) | 0.09889 (10) | 0.0279 (4) | |
| H26A | 0.0150 | 0.4809 | 0.1381 | 0.042* | |
| H26B | −0.0286 | 0.3731 | 0.1065 | 0.042* | |
| H26C | −0.0259 | 0.4632 | 0.0518 | 0.042* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ti1 | 0.01437 (14) | 0.01316 (13) | 0.01128 (13) | 0.00042 (10) | 0.00319 (9) | 0.00035 (9) |
| O1 | 0.0175 (5) | 0.0147 (5) | 0.0178 (5) | 0.0012 (4) | 0.0042 (4) | 0.0013 (4) |
| O2 | 0.0170 (5) | 0.0156 (5) | 0.0125 (5) | 0.0015 (4) | 0.0016 (4) | −0.0008 (4) |
| O3 | 0.0177 (5) | 0.0219 (5) | 0.0178 (5) | 0.0005 (4) | 0.0068 (4) | 0.0032 (4) |
| O4 | 0.0201 (5) | 0.0170 (5) | 0.0130 (5) | −0.0005 (4) | 0.0013 (4) | 0.0005 (4) |
| N1 | 0.0133 (6) | 0.0169 (6) | 0.0119 (6) | −0.0007 (5) | 0.0017 (5) | −0.0018 (4) |
| N2 | 0.0132 (6) | 0.0164 (6) | 0.0144 (6) | −0.0013 (5) | 0.0041 (5) | 0.0001 (5) |
| C1 | 0.0155 (7) | 0.0176 (7) | 0.0158 (7) | −0.0004 (6) | −0.0006 (5) | −0.0037 (5) |
| C2 | 0.0216 (8) | 0.0172 (7) | 0.0240 (8) | 0.0025 (6) | −0.0016 (6) | −0.0030 (6) |
| C3 | 0.0224 (8) | 0.0231 (8) | 0.0296 (9) | 0.0087 (7) | −0.0013 (7) | −0.0095 (7) |
| C4 | 0.0170 (8) | 0.0343 (9) | 0.0262 (8) | 0.0060 (7) | 0.0039 (6) | −0.0099 (7) |
| C5 | 0.0136 (7) | 0.0289 (8) | 0.0177 (7) | 0.0009 (6) | 0.0011 (6) | −0.0054 (6) |
| C6 | 0.0131 (7) | 0.0185 (7) | 0.0133 (7) | 0.0000 (6) | −0.0005 (5) | −0.0034 (5) |
| C7 | 0.0162 (8) | 0.0388 (10) | 0.0197 (8) | −0.0011 (7) | 0.0071 (6) | −0.0023 (7) |
| C8 | 0.0192 (8) | 0.0305 (9) | 0.0189 (8) | −0.0048 (7) | 0.0049 (6) | 0.0035 (6) |
| C9 | 0.0154 (7) | 0.0214 (7) | 0.0129 (7) | −0.0034 (6) | 0.0003 (5) | 0.0001 (5) |
| C10 | 0.0216 (8) | 0.0205 (8) | 0.0214 (8) | −0.0019 (6) | 0.0056 (6) | 0.0045 (6) |
| C11 | 0.0128 (7) | 0.0189 (7) | 0.0139 (7) | 0.0002 (5) | 0.0034 (5) | 0.0007 (5) |
| C12 | 0.0196 (8) | 0.0188 (7) | 0.0205 (8) | 0.0022 (6) | 0.0042 (6) | 0.0016 (6) |
| C13 | 0.0208 (8) | 0.0237 (8) | 0.0223 (8) | 0.0055 (6) | 0.0025 (6) | 0.0077 (6) |
| C14 | 0.0173 (8) | 0.0296 (8) | 0.0164 (7) | 0.0009 (6) | 0.0010 (6) | 0.0047 (6) |
| C15 | 0.0136 (7) | 0.0240 (8) | 0.0140 (7) | −0.0016 (6) | 0.0042 (6) | 0.0013 (6) |
| C16 | 0.0122 (7) | 0.0182 (7) | 0.0141 (7) | −0.0002 (5) | 0.0049 (5) | 0.0014 (5) |
| C17 | 0.0152 (7) | 0.0301 (8) | 0.0142 (7) | −0.0047 (6) | 0.0030 (6) | −0.0032 (6) |
| C18 | 0.0183 (8) | 0.0221 (8) | 0.0191 (7) | −0.0062 (6) | 0.0052 (6) | −0.0061 (6) |
| C19 | 0.0151 (7) | 0.0188 (7) | 0.0182 (7) | −0.0037 (6) | 0.0057 (6) | −0.0018 (6) |
| C20 | 0.0278 (9) | 0.0167 (7) | 0.0238 (8) | −0.0025 (6) | 0.0009 (7) | −0.0008 (6) |
| C21 | 0.0189 (8) | 0.0216 (8) | 0.0210 (8) | −0.0041 (6) | 0.0081 (6) | −0.0003 (6) |
| C22 | 0.0325 (10) | 0.0447 (11) | 0.0233 (9) | 0.0086 (8) | 0.0156 (7) | 0.0071 (8) |
| C23 | 0.0180 (8) | 0.0340 (9) | 0.0305 (9) | 0.0017 (7) | 0.0059 (7) | 0.0053 (7) |
| C24 | 0.0218 (8) | 0.0189 (7) | 0.0130 (7) | 0.0004 (6) | 0.0024 (6) | 0.0019 (5) |
| C25 | 0.0447 (11) | 0.0302 (9) | 0.0160 (8) | 0.0091 (8) | 0.0031 (7) | −0.0011 (7) |
| C26 | 0.0225 (9) | 0.0362 (10) | 0.0245 (8) | 0.0057 (7) | 0.0037 (7) | 0.0071 (7) |
| Ti1—O3 | 1.7766 (11) | C12—C13 | 1.414 (2) |
| Ti1—O4 | 1.8255 (10) | C12—H12 | 0.9500 |
| Ti1—O2 | 1.9130 (10) | C13—C14 | 1.368 (2) |
| Ti1—O1 | 1.9255 (10) | C13—H13 | 0.9500 |
| Ti1—N2 | 2.3822 (12) | C14—C15 | 1.416 (2) |
| Ti1—N1 | 2.4130 (12) | C14—H14 | 0.9500 |
| O1—C1 | 1.3266 (18) | C15—C16 | 1.413 (2) |
| O2—C11 | 1.3338 (17) | C15—C17 | 1.413 (2) |
| O3—C21 | 1.4153 (18) | C17—C18 | 1.359 (2) |
| O4—C24 | 1.4239 (17) | C17—H17 | 0.9500 |
| N1—C9 | 1.3311 (19) | C18—C19 | 1.422 (2) |
| N1—C6 | 1.3756 (19) | C18—H18 | 0.9500 |
| N2—C19 | 1.3270 (19) | C19—C20 | 1.496 (2) |
| N2—C16 | 1.3731 (19) | C20—H20A | 0.9800 |
| C1—C2 | 1.382 (2) | C20—H20B | 0.9800 |
| C1—C6 | 1.419 (2) | C20—H20C | 0.9800 |
| C2—C3 | 1.407 (2) | C21—C23 | 1.511 (2) |
| C2—H2 | 0.9500 | C21—C22 | 1.515 (2) |
| C3—C4 | 1.365 (3) | C21—H21 | 1.0000 |
| C3—H3 | 0.9500 | C22—H22A | 0.9800 |
| C4—C5 | 1.418 (2) | C22—H22B | 0.9800 |
| C4—H4 | 0.9500 | C22—H22C | 0.9800 |
| C5—C7 | 1.409 (2) | C23—H23A | 0.9800 |
| C5—C6 | 1.414 (2) | C23—H23B | 0.9800 |
| C7—C8 | 1.360 (2) | C23—H23C | 0.9800 |
| C7—H7 | 0.9500 | C24—C25 | 1.512 (2) |
| C8—C9 | 1.421 (2) | C24—C26 | 1.517 (2) |
| C8—H8 | 0.9500 | C24—H24 | 1.0000 |
| C9—C10 | 1.497 (2) | C25—H25A | 0.9800 |
| C10—H10A | 0.9800 | C25—H25B | 0.9800 |
| C10—H10B | 0.9800 | C25—H25C | 0.9800 |
| C10—H10C | 0.9800 | C26—H26A | 0.9800 |
| C11—C12 | 1.380 (2) | C26—H26B | 0.9800 |
| C11—C16 | 1.419 (2) | C26—H26C | 0.9800 |
| O3—Ti1—O4 | 101.96 (5) | C14—C13—C12 | 121.83 (15) |
| O3—Ti1—O2 | 101.84 (5) | C14—C13—H13 | 119.1 |
| O4—Ti1—O2 | 95.62 (4) | C12—C13—H13 | 119.1 |
| O3—Ti1—O1 | 93.07 (5) | C13—C14—C15 | 119.54 (14) |
| O4—Ti1—O1 | 97.56 (5) | C13—C14—H14 | 120.2 |
| O2—Ti1—O1 | 157.58 (4) | C15—C14—H14 | 120.2 |
| O3—Ti1—N2 | 90.48 (5) | C16—C15—C17 | 116.11 (14) |
| O4—Ti1—N2 | 165.52 (4) | C16—C15—C14 | 119.09 (14) |
| O2—Ti1—N2 | 74.36 (4) | C17—C15—C14 | 124.74 (14) |
| O1—Ti1—N2 | 89.03 (4) | N2—C16—C15 | 123.90 (14) |
| O3—Ti1—N1 | 164.98 (5) | N2—C16—C11 | 115.65 (13) |
| O4—Ti1—N1 | 87.60 (4) | C15—C16—C11 | 120.37 (14) |
| O2—Ti1—N1 | 88.54 (4) | C18—C17—C15 | 119.67 (14) |
| O1—Ti1—N1 | 74.02 (4) | C18—C17—H17 | 120.2 |
| N2—Ti1—N1 | 81.82 (4) | C15—C17—H17 | 120.2 |
| C1—O1—Ti1 | 125.12 (9) | C17—C18—C19 | 120.95 (14) |
| C11—O2—Ti1 | 124.87 (9) | C17—C18—H18 | 119.5 |
| C21—O3—Ti1 | 154.13 (10) | C19—C18—H18 | 119.5 |
| C24—O4—Ti1 | 126.66 (9) | N2—C19—C18 | 120.93 (14) |
| C9—N1—C6 | 117.94 (13) | N2—C19—C20 | 120.36 (14) |
| C9—N1—Ti1 | 134.90 (10) | C18—C19—C20 | 118.70 (13) |
| C6—N1—Ti1 | 107.09 (9) | C19—C20—H20A | 109.5 |
| C19—N2—C16 | 118.24 (13) | C19—C20—H20B | 109.5 |
| C19—N2—Ti1 | 134.14 (10) | H20A—C20—H20B | 109.5 |
| C16—N2—Ti1 | 107.62 (9) | C19—C20—H20C | 109.5 |
| O1—C1—C2 | 123.29 (14) | H20A—C20—H20C | 109.5 |
| O1—C1—C6 | 117.65 (13) | H20B—C20—H20C | 109.5 |
| C2—C1—C6 | 119.06 (14) | O3—C21—C23 | 110.24 (12) |
| C1—C2—C3 | 120.43 (15) | O3—C21—C22 | 108.63 (13) |
| C1—C2—H2 | 119.8 | C23—C21—C22 | 112.47 (14) |
| C3—C2—H2 | 119.8 | O3—C21—H21 | 108.5 |
| C4—C3—C2 | 121.38 (15) | C23—C21—H21 | 108.5 |
| C4—C3—H3 | 119.3 | C22—C21—H21 | 108.5 |
| C2—C3—H3 | 119.3 | C21—C22—H22A | 109.5 |
| C3—C4—C5 | 119.79 (15) | C21—C22—H22B | 109.5 |
| C3—C4—H4 | 120.1 | H22A—C22—H22B | 109.5 |
| C5—C4—H4 | 120.1 | C21—C22—H22C | 109.5 |
| C7—C5—C6 | 116.69 (14) | H22A—C22—H22C | 109.5 |
| C7—C5—C4 | 124.21 (15) | H22B—C22—H22C | 109.5 |
| C6—C5—C4 | 119.09 (15) | C21—C23—H23A | 109.5 |
| N1—C6—C5 | 123.64 (14) | C21—C23—H23B | 109.5 |
| N1—C6—C1 | 116.11 (13) | H23A—C23—H23B | 109.5 |
| C5—C6—C1 | 120.24 (14) | C21—C23—H23C | 109.5 |
| C8—C7—C5 | 119.49 (15) | H23A—C23—H23C | 109.5 |
| C8—C7—H7 | 120.3 | H23B—C23—H23C | 109.5 |
| C5—C7—H7 | 120.3 | O4—C24—C25 | 108.89 (12) |
| C7—C8—C9 | 120.86 (15) | O4—C24—C26 | 109.19 (12) |
| C7—C8—H8 | 119.6 | C25—C24—C26 | 112.20 (14) |
| C9—C8—H8 | 119.6 | O4—C24—H24 | 108.8 |
| N1—C9—C8 | 121.34 (14) | C25—C24—H24 | 108.8 |
| N1—C9—C10 | 120.18 (13) | C26—C24—H24 | 108.8 |
| C8—C9—C10 | 118.48 (13) | C24—C25—H25A | 109.5 |
| C9—C10—H10A | 109.5 | C24—C25—H25B | 109.5 |
| C9—C10—H10B | 109.5 | H25A—C25—H25B | 109.5 |
| H10A—C10—H10B | 109.5 | C24—C25—H25C | 109.5 |
| C9—C10—H10C | 109.5 | H25A—C25—H25C | 109.5 |
| H10A—C10—H10C | 109.5 | H25B—C25—H25C | 109.5 |
| H10B—C10—H10C | 109.5 | C24—C26—H26A | 109.5 |
| O2—C11—C12 | 123.48 (13) | C24—C26—H26B | 109.5 |
| O2—C11—C16 | 117.07 (13) | H26A—C26—H26B | 109.5 |
| C12—C11—C16 | 119.45 (13) | C24—C26—H26C | 109.5 |
| C11—C12—C13 | 119.68 (15) | H26A—C26—H26C | 109.5 |
| C11—C12—H12 | 120.2 | H26B—C26—H26C | 109.5 |
| C13—C12—H12 | 120.2 | ||
| O3—Ti1—O1—C1 | −171.18 (11) | Ti1—N1—C6—C1 | −0.15 (14) |
| O4—Ti1—O1—C1 | 86.32 (11) | C7—C5—C6—N1 | −1.2 (2) |
| O2—Ti1—O1—C1 | −39.19 (19) | C4—C5—C6—N1 | 179.55 (14) |
| N2—Ti1—O1—C1 | −80.75 (11) | C7—C5—C6—C1 | 178.57 (14) |
| N1—Ti1—O1—C1 | 1.02 (11) | C4—C5—C6—C1 | −0.6 (2) |
| O3—Ti1—O2—C11 | 91.30 (11) | O1—C1—C6—N1 | 0.93 (19) |
| O4—Ti1—O2—C11 | −165.20 (11) | C2—C1—C6—N1 | −179.29 (13) |
| O1—Ti1—O2—C11 | −39.37 (18) | O1—C1—C6—C5 | −178.89 (13) |
| N2—Ti1—O2—C11 | 4.16 (10) | C2—C1—C6—C5 | 0.9 (2) |
| N1—Ti1—O2—C11 | −77.75 (11) | C6—C5—C7—C8 | −0.6 (2) |
| O4—Ti1—O3—C21 | −112.2 (2) | C4—C5—C7—C8 | 178.58 (15) |
| O2—Ti1—O3—C21 | −13.8 (2) | C5—C7—C8—C9 | 1.4 (2) |
| O1—Ti1—O3—C21 | 149.4 (2) | C6—N1—C9—C8 | −1.4 (2) |
| N2—Ti1—O3—C21 | 60.3 (2) | Ti1—N1—C9—C8 | −177.92 (10) |
| N1—Ti1—O3—C21 | 119.1 (2) | C6—N1—C9—C10 | 178.99 (13) |
| O3—Ti1—O4—C24 | −50.83 (12) | Ti1—N1—C9—C10 | 2.4 (2) |
| O2—Ti1—O4—C24 | −154.22 (11) | C7—C8—C9—N1 | −0.4 (2) |
| O1—Ti1—O4—C24 | 43.96 (12) | C7—C8—C9—C10 | 179.26 (15) |
| N2—Ti1—O4—C24 | 160.41 (16) | Ti1—O2—C11—C12 | 178.57 (11) |
| N1—Ti1—O4—C24 | 117.49 (11) | Ti1—O2—C11—C16 | −1.88 (18) |
| O3—Ti1—N1—C9 | −152.04 (17) | O2—C11—C12—C13 | −178.34 (14) |
| O4—Ti1—N1—C9 | 77.85 (14) | C16—C11—C12—C13 | 2.1 (2) |
| O2—Ti1—N1—C9 | −17.84 (14) | C11—C12—C13—C14 | −0.8 (2) |
| O1—Ti1—N1—C9 | 176.41 (14) | C12—C13—C14—C15 | −1.1 (2) |
| N2—Ti1—N1—C9 | −92.25 (14) | C13—C14—C15—C16 | 1.7 (2) |
| O3—Ti1—N1—C6 | 31.1 (2) | C13—C14—C15—C17 | −175.58 (15) |
| O4—Ti1—N1—C6 | −98.96 (9) | C19—N2—C16—C15 | 3.5 (2) |
| O2—Ti1—N1—C6 | 165.34 (9) | Ti1—N2—C16—C15 | −176.65 (11) |
| O1—Ti1—N1—C6 | −0.40 (9) | C19—N2—C16—C11 | −173.27 (13) |
| N2—Ti1—N1—C6 | 90.94 (9) | Ti1—N2—C16—C11 | 6.53 (14) |
| O3—Ti1—N2—C19 | 71.95 (14) | C17—C15—C16—N2 | 0.4 (2) |
| O4—Ti1—N2—C19 | −138.53 (18) | C14—C15—C16—N2 | −177.12 (13) |
| O2—Ti1—N2—C19 | 174.12 (14) | C17—C15—C16—C11 | 177.10 (13) |
| O1—Ti1—N2—C19 | −21.11 (14) | C14—C15—C16—C11 | −0.4 (2) |
| N1—Ti1—N2—C19 | −95.11 (14) | O2—C11—C16—N2 | −4.13 (19) |
| O3—Ti1—N2—C16 | −107.81 (9) | C12—C11—C16—N2 | 175.45 (13) |
| O4—Ti1—N2—C16 | 41.7 (2) | O2—C11—C16—C15 | 178.93 (12) |
| O2—Ti1—N2—C16 | −5.64 (9) | C12—C11—C16—C15 | −1.5 (2) |
| O1—Ti1—N2—C16 | 159.13 (9) | C16—C15—C17—C18 | −3.3 (2) |
| N1—Ti1—N2—C16 | 85.13 (9) | C14—C15—C17—C18 | 174.09 (15) |
| Ti1—O1—C1—C2 | 178.74 (11) | C15—C17—C18—C19 | 2.3 (2) |
| Ti1—O1—C1—C6 | −1.49 (18) | C16—N2—C19—C18 | −4.6 (2) |
| O1—C1—C2—C3 | 179.34 (14) | Ti1—N2—C19—C18 | 175.66 (10) |
| C6—C1—C2—C3 | −0.4 (2) | C16—N2—C19—C20 | 174.44 (13) |
| C1—C2—C3—C4 | −0.3 (2) | Ti1—N2—C19—C20 | −5.3 (2) |
| C2—C3—C4—C5 | 0.6 (2) | C17—C18—C19—N2 | 1.8 (2) |
| C3—C4—C5—C7 | −179.23 (16) | C17—C18—C19—C20 | −177.27 (14) |
| C3—C4—C5—C6 | −0.1 (2) | Ti1—O3—C21—C23 | 8.2 (3) |
| C9—N1—C6—C5 | 2.2 (2) | Ti1—O3—C21—C22 | 131.9 (2) |
| Ti1—N1—C6—C5 | 179.66 (12) | Ti1—O4—C24—C25 | 132.10 (12) |
| C9—N1—C6—C1 | −177.60 (13) | Ti1—O4—C24—C26 | −105.08 (14) |
The authors thank the Vice-President's Office for Research Affairs of Shahid Beheshti University and the University of Malaya for supporting this work.
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