Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043346/at2388sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043346/at2388Isup2.hkl |
CCDC reference: 664186
The title compound (I) was synthesized according to the method described by Zhang et al. (2007). X-ray quality crystals of (I) (0.2 mmol) were grown from a tetrahydrofuran solution (10 ml) at ambient temperature.
H atoms were geometrically positioned and refined using a riding model with fixed individual displacement parameters [Uiso(H) = 1.2 Ueq(C,O) or Uiso(H) = 1.5 Ueq(Cmethyl)] and C—H ranging from 0.95Å to 0.99 Å. The coordinates of the hydroxyl H atom were refined. The C—C distance of the the molecules were refined with a distance restraint of 1.50 (1) Å.
Careful hydrolysis of the homoditopic phenylene-bridged Li and K scorpionates [m-(pz2BtBu)2C6H4]2- leads to the corresponding heteroditopic derivative [m-(pz(HO)BtBu)(pz2BtBu)C6H4]2-. We report here the X-ray crystal structure analysis of the macrocyclic complex (I). Very recently we have described the synthesis of the metallomacrocycle (I) (Zhang et al., 2007). X-ray quality crystals of the macrocycle (I) were grown from a tetrahydrofuran solution at ambient temperature.
Now we present a pseudopolymorph of this complex crystallized from tetrahydrofuran (Fig. 1). Both structures feature dinuclear complexes located on a centre of inversion. The title complex crystallizes with two molecules of tetrahydrofuran in the unit cell. It is noteworthy, that the hydroxyl H atom is shielded from any classical hydrogen bond acceptor. There is just a short contact to the centre of an aromatic ring [O1—H1 0.72 (5) Å, H1···cog(C41i—C46i) 2.48 Å, O1—H1···cog 132.4°; symmetry operator (i): 1 - x, 1 - y, 1 - z]. A least-squares of the complexes of the two pseudopolymorphs fitting all non-H atoms (r.m.s. deviation 0.091 Å) (Fig. 2) shows that the molecular conformations are almost identical. Thus, the solvent molecules in both crystal structures have no influence on the conformation of the complex.
For a related compound and synthesis, see: Zhang et al. (2007). Please provide figure 1; current figure 1 is same as figure 2.
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).
[Fe2(C23H32B2N6O)2]·2C4H8O | Z = 1 |
Mr = 1116.24 | F(000) = 592 |
Triclinic, P1 | Dx = 1.273 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.645 (2) Å | Cell parameters from 10281 reflections |
b = 12.363 (2) Å | θ = 3.4–25.8° |
c = 12.507 (2) Å | µ = 0.55 mm−1 |
α = 71.619 (12)° | T = 173 K |
β = 63.139 (12)° | Block, colourless |
γ = 66.862 (13)° | 0.32 × 0.24 × 0.13 mm |
V = 1456.1 (5) Å3 |
STOE IPDS II two-circle diffractometer | 5438 independent reflections |
Radiation source: fine-focus sealed tube | 3411 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.079 |
ω scans | θmax = 25.7°, θmin = 3.5° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −14→14 |
Tmin = 0.843, Tmax = 0.932 | k = −14→15 |
12022 measured reflections | l = −15→15 |
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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.155 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.89 | w = 1/[σ2(Fo2) + (0.0841P)2] where P = (Fo2 + 2Fc2)/3 |
5438 reflections | (Δ/σ)max = 0.006 |
346 parameters | Δρmax = 0.71 e Å−3 |
3 restraints | Δρmin = −0.48 e Å−3 |
[Fe2(C23H32B2N6O)2]·2C4H8O | γ = 66.862 (13)° |
Mr = 1116.24 | V = 1456.1 (5) Å3 |
Triclinic, P1 | Z = 1 |
a = 11.645 (2) Å | Mo Kα radiation |
b = 12.363 (2) Å | µ = 0.55 mm−1 |
c = 12.507 (2) Å | T = 173 K |
α = 71.619 (12)° | 0.32 × 0.24 × 0.13 mm |
β = 63.139 (12)° |
STOE IPDS II two-circle diffractometer | 5438 independent reflections |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | 3411 reflections with I > 2σ(I) |
Tmin = 0.843, Tmax = 0.932 | Rint = 0.079 |
12022 measured reflections |
R[F2 > 2σ(F2)] = 0.063 | 3 restraints |
wR(F2) = 0.155 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.89 | Δρmax = 0.71 e Å−3 |
5438 reflections | Δρmin = −0.48 e Å−3 |
346 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.67506 (6) | 0.23657 (5) | 0.43545 (5) | 0.03806 (19) | |
B1 | 0.6272 (4) | 0.6466 (4) | 0.4266 (4) | 0.0347 (9) | |
C1 | 0.7258 (4) | 0.6458 (4) | 0.4873 (4) | 0.0446 (10) | |
C16 | 0.6609 (5) | 0.7524 (5) | 0.5551 (5) | 0.0614 (13) | |
H16A | 0.6451 | 0.8269 | 0.4982 | 0.092* | |
H16B | 0.7215 | 0.7525 | 0.5898 | 0.092* | |
H16C | 0.5750 | 0.7458 | 0.6206 | 0.092* | |
C17 | 0.8641 (5) | 0.6558 (4) | 0.3918 (5) | 0.0584 (12) | |
H17A | 0.8517 | 0.7278 | 0.3311 | 0.088* | |
H17B | 0.9115 | 0.5854 | 0.3517 | 0.088* | |
H17C | 0.9172 | 0.6606 | 0.4316 | 0.088* | |
C18 | 0.7467 (5) | 0.5330 (4) | 0.5815 (4) | 0.0534 (11) | |
H18A | 0.7884 | 0.4625 | 0.5421 | 0.080* | |
H18B | 0.6594 | 0.5289 | 0.6461 | 0.080* | |
H18C | 0.8055 | 0.5354 | 0.6167 | 0.080* | |
O1 | 0.4944 (3) | 0.6315 (2) | 0.5255 (3) | 0.0378 (6) | |
H1 | 0.486 (5) | 0.577 (4) | 0.568 (4) | 0.045* | |
B2 | 0.9482 (4) | 0.2460 (4) | 0.2463 (4) | 0.0372 (10) | |
C2 | 1.0880 (4) | 0.2689 (4) | 0.1373 (4) | 0.0451 (10) | |
C26 | 1.2155 (4) | 0.1607 (4) | 0.1204 (5) | 0.0588 (12) | |
H26A | 1.2004 | 0.0955 | 0.1050 | 0.088* | |
H26B | 1.2358 | 0.1346 | 0.1942 | 0.088* | |
H26C | 1.2916 | 0.1833 | 0.0512 | 0.088* | |
C27 | 1.0681 (5) | 0.3157 (4) | 0.0148 (4) | 0.0559 (12) | |
H27A | 1.0500 | 0.2550 | −0.0051 | 0.084* | |
H27B | 1.1498 | 0.3333 | −0.0495 | 0.084* | |
H27C | 0.9917 | 0.3886 | 0.0213 | 0.084* | |
C28 | 1.1163 (5) | 0.3695 (4) | 0.1599 (5) | 0.0547 (11) | |
H28A | 1.0363 | 0.4394 | 0.1716 | 0.082* | |
H28B | 1.1924 | 0.3909 | 0.0898 | 0.082* | |
H28C | 1.1382 | 0.3423 | 0.2329 | 0.082* | |
N11 | 0.8418 (3) | 0.1957 (3) | 0.4743 (3) | 0.0384 (7) | |
N12 | 0.9571 (3) | 0.2016 (3) | 0.3765 (3) | 0.0363 (7) | |
C13 | 1.0580 (4) | 0.1641 (4) | 0.4176 (4) | 0.0451 (10) | |
H13 | 1.1492 | 0.1607 | 0.3676 | 0.054* | |
C14 | 1.0105 (5) | 0.1319 (4) | 0.5403 (4) | 0.0510 (11) | |
H14 | 1.0597 | 0.1020 | 0.5921 | 0.061* | |
C15 | 0.8726 (5) | 0.1526 (4) | 0.5735 (4) | 0.0472 (10) | |
H15 | 0.8104 | 0.1384 | 0.6542 | 0.057* | |
N21 | 0.7824 (3) | 0.1335 (3) | 0.3015 (3) | 0.0377 (7) | |
N22 | 0.9084 (3) | 0.1441 (3) | 0.2278 (3) | 0.0374 (7) | |
C23 | 0.9705 (5) | 0.0626 (4) | 0.1544 (4) | 0.0466 (10) | |
H23 | 1.0594 | 0.0507 | 0.0946 | 0.056* | |
C24 | 0.8853 (5) | −0.0011 (4) | 0.1795 (4) | 0.0496 (11) | |
H24 | 0.9026 | −0.0642 | 0.1413 | 0.060* | |
C25 | 0.7695 (5) | 0.0458 (4) | 0.2716 (4) | 0.0456 (10) | |
H25 | 0.6915 | 0.0195 | 0.3086 | 0.055* | |
N31 | 0.5511 (3) | 0.1507 (3) | 0.5870 (3) | 0.0409 (8) | |
N32 | 0.4261 (3) | 0.2227 (3) | 0.6412 (3) | 0.0357 (7) | |
C33 | 0.3659 (5) | 0.1651 (4) | 0.7500 (4) | 0.0456 (10) | |
H33 | 0.2777 | 0.1966 | 0.8057 | 0.055* | |
C34 | 0.4508 (5) | 0.0533 (4) | 0.7695 (4) | 0.0548 (11) | |
H34 | 0.4346 | −0.0074 | 0.8388 | 0.066* | |
C35 | 0.5645 (5) | 0.0494 (4) | 0.6655 (4) | 0.0512 (11) | |
H35 | 0.6431 | −0.0174 | 0.6513 | 0.061* | |
C41 | 0.8185 (4) | 0.3640 (3) | 0.2563 (3) | 0.0344 (8) | |
C42 | 0.7845 (4) | 0.4487 (3) | 0.3267 (3) | 0.0337 (8) | |
H42 | 0.8367 | 0.4323 | 0.3735 | 0.040* | |
C43 | 0.6796 (3) | 0.5553 (3) | 0.3330 (3) | 0.0328 (8) | |
C44 | 0.6057 (4) | 0.5772 (3) | 0.2612 (4) | 0.0368 (8) | |
H44 | 0.5330 | 0.6484 | 0.2627 | 0.044* | |
C45 | 0.6361 (4) | 0.4975 (4) | 0.1885 (4) | 0.0394 (9) | |
H45 | 0.5851 | 0.5151 | 0.1403 | 0.047* | |
C46 | 0.7406 (4) | 0.3923 (4) | 0.1858 (3) | 0.0382 (9) | |
H46 | 0.7602 | 0.3383 | 0.1358 | 0.046* | |
O51 | 0.2229 (15) | 0.7421 (11) | 0.1334 (15) | 0.305 (8) | |
C52 | 0.2894 (18) | 0.8316 (14) | 0.0926 (15) | 0.203 (7) | |
H52A | 0.2883 | 0.8553 | 0.1617 | 0.244* | |
H52B | 0.2481 | 0.9031 | 0.0436 | 0.244* | |
C53 | 0.4281 (17) | 0.7680 (13) | 0.0174 (15) | 0.332 (19) | |
H53A | 0.4875 | 0.7364 | 0.0641 | 0.399* | |
H53B | 0.4665 | 0.8225 | −0.0566 | 0.399* | |
C54 | 0.4151 (11) | 0.6687 (18) | −0.0155 (10) | 0.273 (14) | |
H54A | 0.3975 | 0.6960 | −0.0915 | 0.327* | |
H54B | 0.4991 | 0.6011 | −0.0277 | 0.327* | |
C55 | 0.3015 (14) | 0.6316 (10) | 0.0861 (10) | 0.158 (5) | |
H55A | 0.3315 | 0.5668 | 0.1471 | 0.189* | |
H55B | 0.2511 | 0.6059 | 0.0576 | 0.189* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0325 (3) | 0.0385 (3) | 0.0401 (3) | −0.0055 (2) | −0.0123 (2) | −0.0112 (3) |
B1 | 0.030 (2) | 0.031 (2) | 0.036 (2) | −0.0068 (17) | −0.0083 (17) | −0.0065 (18) |
C1 | 0.043 (2) | 0.041 (2) | 0.055 (3) | −0.0087 (18) | −0.023 (2) | −0.012 (2) |
C16 | 0.065 (3) | 0.057 (3) | 0.079 (3) | −0.005 (2) | −0.041 (3) | −0.028 (3) |
C17 | 0.045 (2) | 0.054 (3) | 0.083 (3) | −0.015 (2) | −0.025 (2) | −0.017 (3) |
C18 | 0.061 (3) | 0.050 (3) | 0.056 (3) | −0.007 (2) | −0.035 (2) | −0.009 (2) |
O1 | 0.0384 (14) | 0.0317 (15) | 0.0375 (16) | −0.0121 (12) | −0.0104 (12) | −0.0022 (12) |
B2 | 0.039 (2) | 0.033 (2) | 0.038 (2) | −0.0060 (18) | −0.0158 (19) | −0.0088 (19) |
C2 | 0.041 (2) | 0.038 (2) | 0.046 (2) | −0.0076 (17) | −0.0095 (18) | −0.0093 (19) |
C26 | 0.039 (2) | 0.055 (3) | 0.068 (3) | −0.006 (2) | −0.008 (2) | −0.022 (2) |
C27 | 0.055 (3) | 0.055 (3) | 0.042 (2) | −0.016 (2) | −0.006 (2) | −0.006 (2) |
C28 | 0.046 (2) | 0.052 (3) | 0.062 (3) | −0.019 (2) | −0.012 (2) | −0.010 (2) |
N11 | 0.0416 (17) | 0.0377 (18) | 0.0355 (18) | −0.0098 (14) | −0.0173 (15) | −0.0038 (14) |
N12 | 0.0354 (16) | 0.0326 (16) | 0.0384 (18) | −0.0056 (13) | −0.0151 (14) | −0.0067 (14) |
C13 | 0.041 (2) | 0.042 (2) | 0.058 (3) | −0.0080 (18) | −0.027 (2) | −0.008 (2) |
C14 | 0.056 (3) | 0.046 (2) | 0.061 (3) | −0.009 (2) | −0.039 (2) | −0.004 (2) |
C15 | 0.058 (3) | 0.040 (2) | 0.044 (2) | −0.012 (2) | −0.024 (2) | −0.0037 (19) |
N21 | 0.0368 (16) | 0.0390 (18) | 0.0372 (17) | −0.0112 (14) | −0.0125 (14) | −0.0085 (14) |
N22 | 0.0375 (17) | 0.0334 (17) | 0.0361 (17) | −0.0052 (13) | −0.0123 (14) | −0.0083 (14) |
C23 | 0.055 (2) | 0.039 (2) | 0.042 (2) | −0.0086 (19) | −0.015 (2) | −0.0126 (19) |
C24 | 0.067 (3) | 0.039 (2) | 0.051 (3) | −0.015 (2) | −0.025 (2) | −0.016 (2) |
C25 | 0.053 (2) | 0.042 (2) | 0.049 (2) | −0.0166 (19) | −0.025 (2) | −0.005 (2) |
N31 | 0.0376 (17) | 0.0328 (17) | 0.051 (2) | −0.0016 (14) | −0.0199 (15) | −0.0112 (16) |
N32 | 0.0355 (16) | 0.0327 (17) | 0.0368 (18) | −0.0100 (14) | −0.0108 (14) | −0.0074 (14) |
C33 | 0.052 (2) | 0.042 (2) | 0.042 (2) | −0.0207 (19) | −0.0134 (19) | −0.0037 (19) |
C34 | 0.070 (3) | 0.041 (2) | 0.054 (3) | −0.019 (2) | −0.031 (2) | 0.007 (2) |
C35 | 0.055 (3) | 0.030 (2) | 0.063 (3) | −0.0039 (19) | −0.028 (2) | −0.004 (2) |
C41 | 0.0351 (19) | 0.034 (2) | 0.0326 (19) | −0.0124 (16) | −0.0110 (16) | −0.0041 (16) |
C42 | 0.0333 (18) | 0.0298 (19) | 0.038 (2) | −0.0080 (15) | −0.0138 (16) | −0.0072 (16) |
C43 | 0.0302 (18) | 0.0296 (18) | 0.0341 (19) | −0.0093 (14) | −0.0091 (15) | −0.0034 (16) |
C44 | 0.0361 (19) | 0.0302 (19) | 0.041 (2) | −0.0052 (15) | −0.0169 (17) | −0.0036 (17) |
C45 | 0.043 (2) | 0.040 (2) | 0.037 (2) | −0.0107 (17) | −0.0211 (17) | −0.0025 (17) |
C46 | 0.044 (2) | 0.039 (2) | 0.0308 (19) | −0.0134 (17) | −0.0128 (17) | −0.0057 (17) |
O51 | 0.276 (14) | 0.186 (10) | 0.390 (19) | −0.067 (10) | −0.006 (13) | −0.154 (12) |
C52 | 0.28 (2) | 0.162 (12) | 0.262 (18) | −0.106 (14) | −0.177 (17) | 0.019 (12) |
C53 | 0.173 (14) | 0.34 (3) | 0.35 (3) | −0.134 (17) | −0.159 (18) | 0.27 (2) |
C54 | 0.086 (7) | 0.60 (4) | 0.111 (8) | 0.005 (13) | −0.031 (6) | −0.185 (16) |
C55 | 0.229 (14) | 0.142 (9) | 0.146 (9) | −0.029 (9) | −0.132 (10) | −0.020 (7) |
Fe1—O1i | 1.973 (3) | C14—C15 | 1.399 (6) |
Fe1—N11 | 2.046 (3) | C14—H14 | 0.9500 |
Fe1—N21 | 2.048 (3) | C15—H15 | 0.9500 |
Fe1—N31 | 2.065 (4) | N21—C25 | 1.331 (5) |
B1—O1 | 1.520 (5) | N21—N22 | 1.369 (5) |
B1—N32i | 1.593 (5) | N22—C23 | 1.339 (5) |
B1—C43 | 1.632 (5) | C23—C24 | 1.371 (7) |
B1—C1 | 1.633 (6) | C23—H23 | 0.9500 |
C1—C18 | 1.533 (6) | C24—C25 | 1.372 (6) |
C1—C17 | 1.536 (7) | C24—H24 | 0.9500 |
C1—C16 | 1.540 (6) | C25—H25 | 0.9500 |
C16—H16A | 0.9800 | N31—C35 | 1.329 (6) |
C16—H16B | 0.9800 | N31—N32 | 1.357 (4) |
C16—H16C | 0.9800 | N32—C33 | 1.330 (5) |
C17—H17A | 0.9800 | N32—B1i | 1.593 (5) |
C17—H17B | 0.9800 | C33—C34 | 1.370 (6) |
C17—H17C | 0.9800 | C33—H33 | 0.9500 |
C18—H18A | 0.9800 | C34—C35 | 1.371 (7) |
C18—H18B | 0.9800 | C34—H34 | 0.9500 |
C18—H18C | 0.9800 | C35—H35 | 0.9500 |
O1—Fe1i | 1.973 (3) | C41—C42 | 1.404 (5) |
O1—H1 | 0.72 (5) | C41—C46 | 1.415 (5) |
B2—N12 | 1.584 (5) | C42—C43 | 1.396 (5) |
B2—N22 | 1.610 (5) | C42—H42 | 0.9500 |
B2—C41 | 1.625 (5) | C43—C44 | 1.408 (5) |
B2—C2 | 1.644 (6) | C44—C45 | 1.387 (5) |
C2—C28 | 1.537 (6) | C44—H44 | 0.9500 |
C2—C26 | 1.540 (6) | C45—C46 | 1.386 (5) |
C2—C27 | 1.547 (6) | C45—H45 | 0.9500 |
C26—H26A | 0.9800 | C46—H46 | 0.9500 |
C26—H26B | 0.9800 | O51—C55 | 1.447 (13) |
C26—H26C | 0.9800 | O51—C52 | 1.429 (17) |
C27—H27A | 0.9800 | C52—C53 | 1.485 (9) |
C27—H27B | 0.9800 | C52—H52A | 0.9900 |
C27—H27C | 0.9800 | C52—H52B | 0.9900 |
C28—H28A | 0.9800 | C53—C54 | 1.491 (10) |
C28—H28B | 0.9800 | C53—H53A | 0.9900 |
C28—H28C | 0.9800 | C53—H53B | 0.9900 |
N11—C15 | 1.337 (5) | C54—C55 | 1.472 (9) |
N11—N12 | 1.357 (5) | C54—H54A | 0.9900 |
N12—C13 | 1.351 (5) | C54—H54B | 0.9900 |
C13—C14 | 1.357 (7) | C55—H55A | 0.9900 |
C13—H13 | 0.9500 | C55—H55B | 0.9900 |
O1i—Fe1—N11 | 130.37 (12) | C13—C14—H14 | 127.8 |
O1i—Fe1—N21 | 135.07 (12) | C15—C14—H14 | 127.8 |
N11—Fe1—N21 | 91.19 (13) | N11—C15—C14 | 109.6 (4) |
O1i—Fe1—N31 | 79.47 (12) | N11—C15—H15 | 125.2 |
N11—Fe1—N31 | 103.53 (13) | C14—C15—H15 | 125.2 |
N21—Fe1—N31 | 110.22 (13) | C25—N21—N22 | 107.1 (3) |
O1—B1—N32i | 99.5 (3) | C25—N21—Fe1 | 136.8 (3) |
O1—B1—C43 | 107.7 (3) | N22—N21—Fe1 | 115.6 (2) |
N32i—B1—C43 | 106.7 (3) | C23—N22—N21 | 108.3 (3) |
O1—B1—C1 | 110.0 (3) | C23—N22—B2 | 135.1 (4) |
N32i—B1—C1 | 110.4 (3) | N21—N22—B2 | 116.6 (3) |
C43—B1—C1 | 120.5 (3) | N22—C23—C24 | 109.1 (4) |
C18—C1—C17 | 108.9 (4) | N22—C23—H23 | 125.5 |
C18—C1—C16 | 106.6 (4) | C24—C23—H23 | 125.5 |
C17—C1—C16 | 107.4 (4) | C23—C24—C25 | 105.3 (4) |
C18—C1—B1 | 111.4 (4) | C23—C24—H24 | 127.3 |
C17—C1—B1 | 112.4 (4) | C25—C24—H24 | 127.3 |
C16—C1—B1 | 109.9 (3) | N21—C25—C24 | 110.2 (4) |
C1—C16—H16A | 109.5 | N21—C25—H25 | 124.9 |
C1—C16—H16B | 109.5 | C24—C25—H25 | 124.9 |
H16A—C16—H16B | 109.5 | C35—N31—N32 | 105.9 (3) |
C1—C16—H16C | 109.5 | C35—N31—Fe1 | 137.6 (3) |
H16A—C16—H16C | 109.5 | N32—N31—Fe1 | 114.5 (2) |
H16B—C16—H16C | 109.5 | C33—N32—N31 | 109.1 (3) |
C1—C17—H17A | 109.5 | C33—N32—B1i | 130.3 (3) |
C1—C17—H17B | 109.5 | N31—N32—B1i | 120.6 (3) |
H17A—C17—H17B | 109.5 | N32—C33—C34 | 109.6 (4) |
C1—C17—H17C | 109.5 | N32—C33—H33 | 125.2 |
H17A—C17—H17C | 109.5 | C34—C33—H33 | 125.2 |
H17B—C17—H17C | 109.5 | C33—C34—C35 | 103.8 (4) |
C1—C18—H18A | 109.5 | C33—C34—H34 | 128.1 |
C1—C18—H18B | 109.5 | C35—C34—H34 | 128.1 |
H18A—C18—H18B | 109.5 | N31—C35—C34 | 111.6 (4) |
C1—C18—H18C | 109.5 | N31—C35—H35 | 124.2 |
H18A—C18—H18C | 109.5 | C34—C35—H35 | 124.2 |
H18B—C18—H18C | 109.5 | C42—C41—C46 | 116.2 (3) |
B1—O1—Fe1i | 123.8 (2) | C42—C41—B2 | 122.1 (3) |
B1—O1—H1 | 125 (4) | C46—C41—B2 | 121.5 (3) |
Fe1i—O1—H1 | 111 (4) | C43—C42—C41 | 124.7 (3) |
N12—B2—N22 | 104.7 (3) | C43—C42—H42 | 117.6 |
N12—B2—C41 | 106.8 (3) | C41—C42—H42 | 117.6 |
N22—B2—C41 | 105.7 (3) | C42—C43—C44 | 116.0 (3) |
N12—B2—C2 | 113.3 (3) | C42—C43—B1 | 125.2 (3) |
N22—B2—C2 | 112.6 (3) | C44—C43—B1 | 118.5 (3) |
C41—B2—C2 | 113.0 (3) | C45—C44—C43 | 121.8 (3) |
C28—C2—C26 | 107.9 (4) | C45—C44—H44 | 119.1 |
C28—C2—C27 | 105.5 (4) | C43—C44—H44 | 119.1 |
C26—C2—C27 | 107.9 (4) | C46—C45—C44 | 120.3 (3) |
C28—C2—B2 | 109.2 (3) | C46—C45—H45 | 119.8 |
C26—C2—B2 | 116.3 (4) | C44—C45—H45 | 119.8 |
C27—C2—B2 | 109.5 (4) | C45—C46—C41 | 121.0 (3) |
C2—C26—H26A | 109.5 | C45—C46—H46 | 119.5 |
C2—C26—H26B | 109.5 | C41—C46—H46 | 119.5 |
H26A—C26—H26B | 109.5 | C55—O51—C52 | 116.5 (13) |
C2—C26—H26C | 109.5 | O51—C52—C53 | 101.5 (13) |
H26A—C26—H26C | 109.5 | O51—C52—H52A | 111.5 |
H26B—C26—H26C | 109.5 | C53—C52—H52A | 111.5 |
C2—C27—H27A | 109.5 | O51—C52—H52B | 111.5 |
C2—C27—H27B | 109.5 | C53—C52—H52B | 111.5 |
H27A—C27—H27B | 109.5 | H52A—C52—H52B | 109.3 |
C2—C27—H27C | 109.5 | C52—C53—C54 | 105.8 (13) |
H27A—C27—H27C | 109.5 | C52—C53—H53A | 110.6 |
H27B—C27—H27C | 109.5 | C54—C53—H53A | 110.6 |
C2—C28—H28A | 109.5 | C52—C53—H53B | 110.6 |
C2—C28—H28B | 109.5 | C54—C53—H53B | 110.6 |
H28A—C28—H28B | 109.5 | H53A—C53—H53B | 108.7 |
C2—C28—H28C | 109.5 | C55—C54—C53 | 106.8 (10) |
H28A—C28—H28C | 109.5 | C55—C54—H54A | 110.4 |
H28B—C28—H28C | 109.5 | C53—C54—H54A | 110.4 |
C15—N11—N12 | 107.8 (3) | C55—C54—H54B | 110.4 |
C15—N11—Fe1 | 136.3 (3) | C53—C54—H54B | 110.4 |
N12—N11—Fe1 | 115.5 (2) | H54A—C54—H54B | 108.6 |
C13—N12—N11 | 107.7 (3) | C54—C55—O51 | 100.1 (10) |
C13—N12—B2 | 134.6 (3) | C54—C55—H55A | 111.8 |
N11—N12—B2 | 117.7 (3) | O51—C55—H55A | 111.8 |
N12—C13—C14 | 110.4 (4) | C54—C55—H55B | 111.8 |
N12—C13—H13 | 124.8 | O51—C55—H55B | 111.8 |
C14—C13—H13 | 124.8 | H55A—C55—H55B | 109.5 |
C13—C14—C15 | 104.4 (4) | ||
O1—B1—C1—C18 | 55.2 (4) | C41—B2—N22—C23 | 134.9 (4) |
N32i—B1—C1—C18 | 164.1 (3) | C2—B2—N22—C23 | 11.0 (6) |
C43—B1—C1—C18 | −70.9 (5) | N12—B2—N22—N21 | 67.6 (4) |
O1—B1—C1—C17 | 177.7 (3) | C41—B2—N22—N21 | −45.0 (4) |
N32i—B1—C1—C17 | −73.4 (4) | C2—B2—N22—N21 | −168.9 (3) |
C43—B1—C1—C17 | 51.6 (5) | N21—N22—C23—C24 | 0.3 (5) |
O1—B1—C1—C16 | −62.7 (5) | B2—N22—C23—C24 | −179.6 (4) |
N32i—B1—C1—C16 | 46.1 (5) | N22—C23—C24—C25 | −0.3 (5) |
C43—B1—C1—C16 | 171.1 (4) | N22—N21—C25—C24 | 0.0 (5) |
N32i—B1—O1—Fe1i | −12.4 (4) | Fe1—N21—C25—C24 | −171.5 (3) |
C43—B1—O1—Fe1i | −123.4 (3) | C23—C24—C25—N21 | 0.1 (5) |
C1—B1—O1—Fe1i | 103.5 (3) | O1i—Fe1—N31—C35 | −165.3 (4) |
N12—B2—C2—C28 | −63.1 (4) | N11—Fe1—N31—C35 | −36.0 (4) |
N22—B2—C2—C28 | 178.4 (3) | N21—Fe1—N31—C35 | 60.4 (4) |
C41—B2—C2—C28 | 58.6 (4) | O1i—Fe1—N31—N32 | −4.4 (2) |
N12—B2—C2—C26 | 59.2 (5) | N11—Fe1—N31—N32 | 124.9 (2) |
N22—B2—C2—C26 | −59.3 (5) | N21—Fe1—N31—N32 | −138.7 (2) |
C41—B2—C2—C26 | −179.1 (4) | C35—N31—N32—C33 | −0.2 (4) |
N12—B2—C2—C27 | −178.2 (3) | Fe1—N31—N32—C33 | −166.9 (3) |
N22—B2—C2—C27 | 63.3 (4) | C35—N31—N32—B1i | −179.6 (3) |
C41—B2—C2—C27 | −56.5 (4) | Fe1—N31—N32—B1i | 13.7 (4) |
O1i—Fe1—N11—C15 | 71.6 (4) | N31—N32—C33—C34 | 0.0 (5) |
N21—Fe1—N11—C15 | −127.1 (4) | B1i—N32—C33—C34 | 179.3 (4) |
N31—Fe1—N11—C15 | −16.0 (4) | N32—C33—C34—C35 | 0.3 (5) |
O1i—Fe1—N11—N12 | −116.0 (2) | N32—N31—C35—C34 | 0.4 (5) |
N21—Fe1—N11—N12 | 45.2 (3) | Fe1—N31—C35—C34 | 162.3 (3) |
N31—Fe1—N11—N12 | 156.4 (2) | C33—C34—C35—N31 | −0.4 (5) |
C15—N11—N12—C13 | −1.2 (4) | N12—B2—C41—C42 | 37.8 (5) |
Fe1—N11—N12—C13 | −175.7 (3) | N22—B2—C41—C42 | 148.9 (4) |
C15—N11—N12—B2 | 177.9 (3) | C2—B2—C41—C42 | −87.5 (4) |
Fe1—N11—N12—B2 | 3.4 (4) | N12—B2—C41—C46 | −147.9 (4) |
N22—B2—N12—C13 | 113.1 (5) | N22—B2—C41—C46 | −36.8 (5) |
C41—B2—N12—C13 | −135.0 (4) | C2—B2—C41—C46 | 86.8 (4) |
C2—B2—N12—C13 | −9.9 (6) | C46—C41—C42—C43 | 1.2 (6) |
N22—B2—N12—N11 | −65.7 (4) | B2—C41—C42—C43 | 175.8 (4) |
C41—B2—N12—N11 | 46.2 (4) | C41—C42—C43—C44 | −0.7 (6) |
C2—B2—N12—N11 | 171.3 (3) | C41—C42—C43—B1 | 172.1 (4) |
N11—N12—C13—C14 | 1.0 (4) | O1—B1—C43—C42 | −105.1 (4) |
B2—N12—C13—C14 | −177.9 (4) | N32i—B1—C43—C42 | 148.9 (4) |
N12—C13—C14—C15 | −0.4 (5) | C1—B1—C43—C42 | 22.1 (6) |
N12—N11—C15—C14 | 1.0 (5) | O1—B1—C43—C44 | 67.6 (4) |
Fe1—N11—C15—C14 | 173.8 (3) | N32i—B1—C43—C44 | −38.5 (4) |
C13—C14—C15—N11 | −0.4 (5) | C1—B1—C43—C44 | −165.2 (4) |
O1i—Fe1—N21—C25 | −72.2 (4) | C42—C43—C44—C45 | −0.3 (6) |
N11—Fe1—N21—C25 | 128.0 (4) | B1—C43—C44—C45 | −173.6 (4) |
N31—Fe1—N21—C25 | 23.2 (4) | C43—C44—C45—C46 | 0.8 (6) |
O1i—Fe1—N21—N22 | 116.8 (3) | C44—C45—C46—C41 | −0.3 (6) |
N11—Fe1—N21—N22 | −42.9 (3) | C42—C41—C46—C45 | −0.7 (6) |
N31—Fe1—N21—N22 | −147.8 (2) | B2—C41—C46—C45 | −175.3 (4) |
C25—N21—N22—C23 | −0.2 (4) | C55—O51—C52—C53 | −4 (2) |
Fe1—N21—N22—C23 | 173.4 (3) | O51—C52—C53—C54 | 20.9 (17) |
C25—N21—N22—B2 | 179.7 (3) | C52—C53—C54—C55 | −31.5 (17) |
Fe1—N21—N22—B2 | −6.7 (4) | C53—C54—C55—O51 | 27.2 (15) |
N12—B2—N22—C23 | −112.5 (5) | C52—O51—C55—C54 | −14.7 (17) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Fe2(C23H32B2N6O)2]·2C4H8O |
Mr | 1116.24 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 11.645 (2), 12.363 (2), 12.507 (2) |
α, β, γ (°) | 71.619 (12), 63.139 (12), 66.862 (13) |
V (Å3) | 1456.1 (5) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.55 |
Crystal size (mm) | 0.32 × 0.24 × 0.13 |
Data collection | |
Diffractometer | STOE IPDS II two-circle diffractometer |
Absorption correction | Multi-scan (MULABS; Spek, 2003; Blessing, 1995) |
Tmin, Tmax | 0.843, 0.932 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12022, 5438, 3411 |
Rint | 0.079 |
(sin θ/λ)max (Å−1) | 0.611 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.155, 0.89 |
No. of reflections | 5438 |
No. of parameters | 346 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.71, −0.48 |
Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1990), XP in SHELXTL-Plus (Sheldrick, 1991), SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).
Careful hydrolysis of the homoditopic phenylene-bridged Li and K scorpionates [m-(pz2BtBu)2C6H4]2- leads to the corresponding heteroditopic derivative [m-(pz(HO)BtBu)(pz2BtBu)C6H4]2-. We report here the X-ray crystal structure analysis of the macrocyclic complex (I). Very recently we have described the synthesis of the metallomacrocycle (I) (Zhang et al., 2007). X-ray quality crystals of the macrocycle (I) were grown from a tetrahydrofuran solution at ambient temperature.
Now we present a pseudopolymorph of this complex crystallized from tetrahydrofuran (Fig. 1). Both structures feature dinuclear complexes located on a centre of inversion. The title complex crystallizes with two molecules of tetrahydrofuran in the unit cell. It is noteworthy, that the hydroxyl H atom is shielded from any classical hydrogen bond acceptor. There is just a short contact to the centre of an aromatic ring [O1—H1 0.72 (5) Å, H1···cog(C41i—C46i) 2.48 Å, O1—H1···cog 132.4°; symmetry operator (i): 1 - x, 1 - y, 1 - z]. A least-squares of the complexes of the two pseudopolymorphs fitting all non-H atoms (r.m.s. deviation 0.091 Å) (Fig. 2) shows that the molecular conformations are almost identical. Thus, the solvent molecules in both crystal structures have no influence on the conformation of the complex.