metal-organic compounds
The title compound, [Ga(CH3)2(C21H17N2O)], synthesized by the reaction of trimethylgallium and 4-methyl-2,6-bis(phenyliminomethyl)phenol, has the Ga atom in a tetrahedral geometry; two molecules form a dimer through a π–π interaction.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805005702/ng6095sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805005702/ng6095Isup2.hkl |
CCDC reference: 270491
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.037
- wR factor = 0.085
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
Computing details top
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Crystal data top
[Ga(CH3)2(C21H17N2O)] | F(000) = 856 |
Mr = 413.15 | Dx = 1.341 Mg m−3 |
Monoclinic, P21/c | Melting point: 445-446 K K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 9.498 (1) Å | Cell parameters from 3581 reflections |
b = 13.028 (1) Å | θ = 2.5–25.4° |
c = 16.598 (2) Å | µ = 1.36 mm−1 |
β = 95.04 (1)° | T = 293 K |
V = 2045.9 (4) Å3 | Block, orange |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 4013 independent reflections |
Radiation source: sealed tube | 2790 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
φ and ω scans | θmax = 26.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −11→11 |
Tmin = 0.73, Tmax = 0.76 | k = −14→16 |
10679 measured reflections | l = −20→17 |
Refinement top
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.025P)2] where P = (Fo2 + 2Fc2)/3 |
4013 reflections | (Δ/σ)max = 0.001 |
247 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Special details top
Geometry. Cg1 Cg1 3.496 (17) 3 y (Cg1···Cg1i, 3.50 (2) Å), the Cg1 being the center of the aromatic ring (C1/C2/C3/C4/C5/C6, i: 1 - x, 1 - y, 1 - z). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Ga1 | 0.78024 (3) | 0.75831 (2) | 0.628870 (17) | 0.04878 (12) | |
N1 | 0.6536 (2) | 0.31899 (18) | 0.65541 (13) | 0.0539 (6) | |
N2 | 0.6321 (2) | 0.79903 (16) | 0.53757 (12) | 0.0448 (5) | |
O1 | 0.72893 (16) | 0.61912 (14) | 0.61645 (10) | 0.0526 (5) | |
C1 | 0.5964 (2) | 0.5882 (2) | 0.60463 (14) | 0.0437 (6) | |
C2 | 0.5619 (2) | 0.4868 (2) | 0.62280 (13) | 0.0446 (6) | |
C3 | 0.4217 (2) | 0.4536 (2) | 0.61086 (14) | 0.0487 (6) | |
H3 | 0.4002 | 0.3864 | 0.6240 | 0.058* | |
C4 | 0.3137 (2) | 0.5177 (2) | 0.58017 (15) | 0.0494 (7) | |
C5 | 0.3481 (2) | 0.6151 (2) | 0.55922 (14) | 0.0476 (7) | |
H5 | 0.2766 | 0.6581 | 0.5372 | 0.057* | |
C6 | 0.4870 (2) | 0.6532 (2) | 0.56944 (14) | 0.0426 (6) | |
C7 | 0.5152 (3) | 0.74829 (19) | 0.53112 (15) | 0.0467 (6) | |
H7 | 0.4413 | 0.7766 | 0.4979 | 0.056* | |
C8 | 0.6748 (3) | 0.4142 (2) | 0.64799 (14) | 0.0502 (6) | |
H8 | 0.7662 | 0.4392 | 0.6590 | 0.060* | |
C9 | 0.1642 (2) | 0.4768 (2) | 0.56474 (18) | 0.0671 (8) | |
H9A | 0.0988 | 0.5331 | 0.5614 | 0.101* | |
H9B | 0.1438 | 0.4322 | 0.6083 | 0.101* | |
H9C | 0.1555 | 0.4392 | 0.5148 | 0.101* | |
C10 | 0.7705 (3) | 0.2511 (2) | 0.67014 (16) | 0.0527 (7) | |
C11 | 0.8939 (3) | 0.2606 (2) | 0.63267 (18) | 0.0644 (8) | |
H11 | 0.9058 | 0.3163 | 0.5989 | 0.077* | |
C12 | 0.9994 (3) | 0.1887 (3) | 0.6446 (2) | 0.0804 (10) | |
H12 | 1.0820 | 0.1957 | 0.6189 | 0.096* | |
C13 | 0.9830 (4) | 0.1068 (3) | 0.6944 (2) | 0.0913 (12) | |
H13 | 1.0544 | 0.0581 | 0.7026 | 0.110* | |
C14 | 0.8617 (4) | 0.0966 (3) | 0.7320 (2) | 0.0869 (11) | |
H14 | 0.8507 | 0.0411 | 0.7661 | 0.104* | |
C15 | 0.7560 (3) | 0.1682 (3) | 0.71943 (18) | 0.0692 (8) | |
H15 | 0.6732 | 0.1602 | 0.7448 | 0.083* | |
C16 | 0.6476 (2) | 0.8856 (2) | 0.48622 (15) | 0.0466 (6) | |
C17 | 0.5937 (3) | 0.8856 (2) | 0.40631 (16) | 0.0591 (8) | |
H17 | 0.5443 | 0.8288 | 0.3848 | 0.071* | |
C18 | 0.6131 (3) | 0.9698 (3) | 0.35853 (19) | 0.0713 (9) | |
H18 | 0.5750 | 0.9704 | 0.3050 | 0.086* | |
C19 | 0.6888 (3) | 1.0535 (3) | 0.3896 (2) | 0.0738 (9) | |
H19 | 0.7019 | 1.1102 | 0.3571 | 0.089* | |
C20 | 0.7439 (3) | 1.0526 (3) | 0.4679 (2) | 0.0686 (8) | |
H20 | 0.7955 | 1.1088 | 0.4887 | 0.082* | |
C21 | 0.7244 (3) | 0.9701 (2) | 0.51637 (17) | 0.0587 (7) | |
H21 | 0.7627 | 0.9704 | 0.5699 | 0.070* | |
C22 | 0.9699 (3) | 0.7731 (2) | 0.5952 (2) | 0.0765 (9) | |
H22A | 1.0349 | 0.7342 | 0.6307 | 0.115* | |
H22B | 0.9965 | 0.8442 | 0.5973 | 0.115* | |
H22C | 0.9720 | 0.7483 | 0.5408 | 0.115* | |
C23 | 0.7033 (3) | 0.8119 (3) | 0.72503 (17) | 0.0764 (9) | |
H23A | 0.6106 | 0.7841 | 0.7289 | 0.115* | |
H23B | 0.6976 | 0.8854 | 0.7216 | 0.115* | |
H23C | 0.7637 | 0.7928 | 0.7720 | 0.115* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Ga1 | 0.04450 (17) | 0.0514 (2) | 0.04959 (18) | −0.00698 (14) | −0.00096 (12) | 0.00031 (14) |
N1 | 0.0504 (13) | 0.0501 (16) | 0.0598 (14) | −0.0072 (12) | −0.0026 (11) | 0.0045 (12) |
N2 | 0.0413 (12) | 0.0460 (14) | 0.0464 (12) | −0.0020 (10) | 0.0007 (9) | −0.0015 (10) |
O1 | 0.0377 (9) | 0.0480 (12) | 0.0708 (12) | −0.0045 (8) | −0.0030 (8) | 0.0034 (9) |
C1 | 0.0440 (14) | 0.0471 (17) | 0.0401 (14) | −0.0055 (12) | 0.0040 (11) | −0.0049 (12) |
C2 | 0.0428 (13) | 0.0513 (17) | 0.0395 (14) | −0.0048 (12) | 0.0016 (11) | −0.0026 (12) |
C3 | 0.0499 (15) | 0.0519 (17) | 0.0446 (15) | −0.0120 (13) | 0.0057 (12) | −0.0025 (13) |
C4 | 0.0401 (14) | 0.061 (2) | 0.0469 (15) | −0.0080 (13) | 0.0050 (12) | −0.0038 (14) |
C5 | 0.0378 (14) | 0.0594 (19) | 0.0453 (14) | 0.0029 (12) | 0.0011 (11) | 0.0004 (13) |
C6 | 0.0388 (13) | 0.0479 (16) | 0.0409 (14) | −0.0029 (12) | 0.0020 (11) | 0.0007 (12) |
C7 | 0.0449 (14) | 0.0499 (18) | 0.0448 (14) | 0.0035 (13) | 0.0000 (11) | −0.0018 (13) |
C8 | 0.0461 (14) | 0.0532 (19) | 0.0503 (15) | −0.0085 (13) | −0.0018 (12) | 0.0009 (14) |
C9 | 0.0443 (15) | 0.081 (2) | 0.0749 (19) | −0.0165 (15) | 0.0004 (14) | −0.0025 (17) |
C10 | 0.0511 (16) | 0.0540 (19) | 0.0507 (15) | −0.0065 (14) | −0.0090 (12) | 0.0021 (14) |
C11 | 0.0573 (17) | 0.067 (2) | 0.0680 (18) | −0.0016 (15) | −0.0022 (15) | 0.0069 (16) |
C12 | 0.064 (2) | 0.090 (3) | 0.085 (2) | 0.013 (2) | −0.0031 (18) | 0.002 (2) |
C13 | 0.091 (3) | 0.081 (3) | 0.096 (3) | 0.031 (2) | −0.023 (2) | −0.005 (2) |
C14 | 0.104 (3) | 0.067 (2) | 0.086 (2) | 0.006 (2) | −0.016 (2) | 0.0185 (19) |
C15 | 0.075 (2) | 0.059 (2) | 0.071 (2) | −0.0053 (17) | −0.0032 (16) | 0.0084 (17) |
C16 | 0.0414 (13) | 0.0470 (17) | 0.0512 (16) | 0.0005 (12) | 0.0028 (12) | 0.0028 (13) |
C17 | 0.0601 (17) | 0.064 (2) | 0.0526 (17) | −0.0114 (15) | −0.0005 (14) | 0.0059 (15) |
C18 | 0.074 (2) | 0.078 (3) | 0.0602 (19) | −0.0053 (18) | −0.0001 (16) | 0.0168 (18) |
C19 | 0.070 (2) | 0.062 (2) | 0.091 (3) | −0.0008 (17) | 0.0147 (18) | 0.0220 (19) |
C20 | 0.0650 (18) | 0.055 (2) | 0.086 (2) | −0.0095 (15) | 0.0057 (17) | 0.0005 (18) |
C21 | 0.0583 (16) | 0.055 (2) | 0.0616 (17) | −0.0063 (14) | −0.0009 (14) | −0.0010 (15) |
C22 | 0.0492 (16) | 0.080 (2) | 0.100 (2) | −0.0112 (15) | 0.0052 (16) | 0.021 (2) |
C23 | 0.097 (2) | 0.078 (3) | 0.0532 (18) | 0.0047 (19) | 0.0024 (17) | −0.0060 (16) |
Geometric parameters (Å, º) top
Ga1—O1 | 1.8843 (18) | C11—C12 | 1.373 (4) |
Ga1—N2 | 2.045 (2) | C11—H11 | 0.9300 |
Ga1—C22 | 1.942 (3) | C12—C13 | 1.366 (5) |
Ga1—C23 | 1.943 (3) | C12—H12 | 0.9300 |
N1—C8 | 1.264 (3) | C13—C14 | 1.364 (4) |
N1—C10 | 1.423 (3) | C13—H13 | 0.9300 |
N2—C7 | 1.289 (3) | C14—C15 | 1.373 (4) |
N2—C16 | 1.429 (3) | C14—H14 | 0.9300 |
O1—C1 | 1.319 (3) | C15—H15 | 0.9300 |
C1—C2 | 1.401 (3) | C16—C17 | 1.379 (3) |
C1—C6 | 1.425 (3) | C16—C21 | 1.389 (4) |
C2—C3 | 1.397 (3) | C17—C18 | 1.375 (4) |
C2—C8 | 1.463 (3) | C17—H17 | 0.9300 |
C3—C4 | 1.384 (4) | C18—C19 | 1.380 (4) |
C3—H3 | 0.9300 | C18—H18 | 0.9300 |
C4—C5 | 1.363 (4) | C19—C20 | 1.358 (4) |
C4—C9 | 1.517 (3) | C19—H19 | 0.9300 |
C5—C6 | 1.406 (3) | C20—C21 | 1.365 (4) |
C5—H5 | 0.9300 | C20—H20 | 0.9300 |
C6—C7 | 1.428 (3) | C21—H21 | 0.9300 |
C7—H7 | 0.9300 | C22—H22A | 0.9600 |
C8—H8 | 0.9300 | C22—H22B | 0.9600 |
C9—H9A | 0.9600 | C22—H22C | 0.9600 |
C9—H9B | 0.9600 | C23—H23A | 0.9600 |
C9—H9C | 0.9600 | C23—H23B | 0.9600 |
C10—C15 | 1.370 (4) | C23—H23C | 0.9600 |
C10—C11 | 1.380 (4) | ||
O1—Ga1—C22 | 107.56 (11) | C12—C11—H11 | 119.6 |
O1—Ga1—C23 | 108.87 (11) | C10—C11—H11 | 119.6 |
O1—Ga1—N2 | 90.81 (8) | C13—C12—C11 | 119.9 (3) |
N2—Ga1—C22 | 110.83 (11) | C13—C12—H12 | 120.0 |
N2—Ga1—C23 | 103.40 (11) | C11—C12—H12 | 120.0 |
C22—Ga1—C23 | 128.77 (14) | C14—C13—C12 | 119.9 (3) |
C8—N1—C10 | 119.8 (2) | C14—C13—H13 | 120.0 |
C7—N2—C16 | 119.2 (2) | C12—C13—H13 | 120.0 |
C7—N2—Ga1 | 117.39 (17) | C13—C14—C15 | 120.0 (3) |
C16—N2—Ga1 | 123.14 (15) | C13—C14—H14 | 120.0 |
C1—O1—Ga1 | 122.94 (16) | C15—C14—H14 | 120.0 |
O1—C1—C2 | 119.6 (2) | C10—C15—C14 | 121.1 (3) |
O1—C1—C6 | 122.1 (2) | C10—C15—H15 | 119.5 |
C2—C1—C6 | 118.2 (2) | C14—C15—H15 | 119.5 |
C3—C2—C1 | 119.9 (2) | C17—C16—C21 | 119.0 (3) |
C3—C2—C8 | 120.4 (3) | C17—C16—N2 | 121.7 (2) |
C1—C2—C8 | 119.4 (2) | C21—C16—N2 | 119.3 (2) |
C4—C3—C2 | 122.2 (3) | C18—C17—C16 | 119.8 (3) |
C4—C3—H3 | 118.9 | C18—C17—H17 | 120.1 |
C2—C3—H3 | 118.9 | C16—C17—H17 | 120.1 |
C5—C4—C3 | 117.9 (2) | C17—C18—C19 | 120.4 (3) |
C5—C4—C9 | 121.7 (2) | C17—C18—H18 | 119.8 |
C3—C4—C9 | 120.2 (3) | C19—C18—H18 | 119.8 |
C4—C5—C6 | 122.8 (2) | C20—C19—C18 | 119.7 (3) |
C4—C5—H5 | 118.6 | C20—C19—H19 | 120.1 |
C6—C5—H5 | 118.6 | C18—C19—H19 | 120.1 |
C5—C6—C1 | 118.8 (2) | C19—C20—C21 | 120.6 (3) |
C5—C6—C7 | 117.6 (2) | C19—C20—H20 | 119.7 |
C1—C6—C7 | 122.6 (2) | C21—C20—H20 | 119.7 |
N2—C7—C6 | 127.0 (2) | C20—C21—C16 | 120.4 (3) |
N2—C7—H7 | 116.5 | C20—C21—H21 | 119.8 |
C6—C7—H7 | 116.5 | C16—C21—H21 | 119.8 |
N1—C8—C2 | 122.9 (2) | Ga1—C22—H22A | 109.5 |
N1—C8—H8 | 118.6 | Ga1—C22—H22B | 109.5 |
C2—C8—H8 | 118.6 | H22A—C22—H22B | 109.5 |
C4—C9—H9A | 109.5 | Ga1—C22—H22C | 109.5 |
C4—C9—H9B | 109.5 | H22A—C22—H22C | 109.5 |
H9A—C9—H9B | 109.5 | H22B—C22—H22C | 109.5 |
C4—C9—H9C | 109.5 | Ga1—C23—H23A | 109.5 |
H9A—C9—H9C | 109.5 | Ga1—C23—H23B | 109.5 |
H9B—C9—H9C | 109.5 | H23A—C23—H23B | 109.5 |
C15—C10—C11 | 118.2 (3) | Ga1—C23—H23C | 109.5 |
C15—C10—N1 | 118.4 (3) | H23A—C23—H23C | 109.5 |
C11—C10—N1 | 123.2 (3) | H23B—C23—H23C | 109.5 |
C12—C11—C10 | 120.8 (3) |