Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101005534/sk1467sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101005534/sk1467Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101005534/sk1467IIsup3.hkl |
CCDC references: 166975; 166976
For related literature, see: Bu et al. (1990); Chen et al. (1995, 1997); Kato et al. (1988); Li et al. (1995, 1997); Liu et al. (1997); Sanz-Medel, Fernandez & Garcia (1987); Sugiyama et al. (1991); Uma & Krishnamurthi (1984); Xiong et al. (1995).
The title complexes were prepared by mixing an aqueous solution of metal nitrate [M = FeIII and CuII] and 2-methyl-8-hydroxyquinoline with heating. The deposits were collected by filtration, washed with water and dried overnight. Deep red compound (I) and blue-green compound (II) were subsequently obtained. Single crystals suitable for X-ray analysis were obtained by recrystallization from EtOH solution at room temperature. It is very difficult to get good quality crystals of compound (II) though many attempts have been made. The crystal used for this report was the best attained after several attempts.
For both compounds, after checking their presence in the difference map, all H atoms were geometrically fixed and allowed to ride on their attached atoms with Uiso = 1.2Ueq for the attached atoms (except for the CH3 moieties where Uiso = 1.5Ueq). The H atoms of the CH3 moieties were refined as rigid rotators.
For compound (II), restraints on the displacement parameters of atoms C1, N1 and O1W were applied.
For both compounds, data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).
[Fe(C10H8NO)3] | F(000) = 2200 |
Mr = 530.37 | Dx = 1.407 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 23.8220 (3) Å | Cell parameters from 8192 reflections |
b = 16.0839 (3) Å | θ = 1.6–29.5° |
c = 15.6819 (3) Å | µ = 0.64 mm−1 |
β = 123.571 (1)° | T = 293 K |
V = 5006.31 (15) Å3 | Block, dark purple |
Z = 8 | 0.48 × 0.40 × 0.08 mm |
Siemens SMART CCD area detector diffractometer | 5734 independent reflections |
Radiation source: fine-focus sealed tube | 3729 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.072 |
Detector resolution: 8.33 pixels mm-1 | θmax = 27.5°, θmin = 1.6° |
ω scans | h = −30→30 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −20→11 |
Tmin = 0.749, Tmax = 0.951 | l = −20→20 |
16629 measured reflections |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0718P)2] where P = (Fo2 + 2Fc2)/3 |
5734 reflections | (Δ/σ)max = 0.002 |
337 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.96 e Å−3 |
[Fe(C10H8NO)3] | V = 5006.31 (15) Å3 |
Mr = 530.37 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 23.8220 (3) Å | µ = 0.64 mm−1 |
b = 16.0839 (3) Å | T = 293 K |
c = 15.6819 (3) Å | 0.48 × 0.40 × 0.08 mm |
β = 123.571 (1)° |
Siemens SMART CCD area detector diffractometer | 5734 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 3729 reflections with I > 2σ(I) |
Tmin = 0.749, Tmax = 0.951 | Rint = 0.072 |
16629 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.142 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | Δρmax = 0.45 e Å−3 |
5734 reflections | Δρmin = −0.96 e Å−3 |
337 parameters |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Coverage of the unique set is over 99% complete. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the duplicate reflections, and was found to be negligible. The structure was solved by direct methods and refined by full-matrix least-squares techniques. |
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 | ||
Fe | 0.199035 (19) | 0.04925 (2) | 0.28179 (3) | 0.03340 (14) | |
O1 | 0.13359 (9) | 0.13849 (12) | 0.23414 (14) | 0.0407 (5) | |
O2 | 0.14913 (10) | −0.03845 (11) | 0.29759 (14) | 0.0380 (5) | |
O3 | 0.26680 (9) | 0.11650 (11) | 0.28312 (15) | 0.0411 (5) | |
N1 | 0.22357 (11) | 0.09900 (14) | 0.43075 (16) | 0.0351 (5) | |
N2 | 0.13879 (11) | 0.00065 (13) | 0.12414 (16) | 0.0303 (5) | |
N3 | 0.29125 (12) | −0.04454 (14) | 0.33399 (17) | 0.0361 (5) | |
C1 | 0.17811 (13) | 0.16089 (16) | 0.4100 (2) | 0.0336 (6) | |
C2 | 0.13053 (13) | 0.18037 (17) | 0.3042 (2) | 0.0335 (6) | |
C3 | 0.08407 (14) | 0.24217 (18) | 0.2805 (2) | 0.0444 (7) | |
H3A | 0.0522 | 0.2550 | 0.2123 | 0.053* | |
C4 | 0.08397 (15) | 0.2866 (2) | 0.3584 (3) | 0.0509 (8) | |
H4A | 0.0522 | 0.3282 | 0.3403 | 0.061* | |
C5 | 0.12908 (16) | 0.2696 (2) | 0.4586 (3) | 0.0498 (8) | |
H5A | 0.1282 | 0.2997 | 0.5084 | 0.060* | |
C6 | 0.17746 (14) | 0.20647 (17) | 0.4877 (2) | 0.0393 (7) | |
C7 | 0.22732 (16) | 0.1848 (2) | 0.5892 (2) | 0.0495 (8) | |
H7A | 0.2295 | 0.2124 | 0.6431 | 0.059* | |
C8 | 0.27208 (17) | 0.1240 (2) | 0.6088 (2) | 0.0498 (8) | |
H8A | 0.3050 | 0.1105 | 0.6763 | 0.060* | |
C9 | 0.26995 (15) | 0.08046 (19) | 0.5285 (2) | 0.0411 (7) | |
C10 | 0.32054 (17) | 0.0144 (2) | 0.5527 (2) | 0.0597 (9) | |
H10A | 0.2977 | −0.0359 | 0.5177 | 0.090* | |
H10B | 0.3473 | 0.0046 | 0.6252 | 0.090* | |
H10C | 0.3491 | 0.0320 | 0.5308 | 0.090* | |
C11 | 0.34102 (14) | 0.00092 (17) | 0.3366 (2) | 0.0372 (6) | |
C12 | 0.32562 (14) | 0.08696 (18) | 0.3078 (2) | 0.0390 (7) | |
C13 | 0.37372 (16) | 0.1341 (2) | 0.3071 (3) | 0.0557 (9) | |
H13A | 0.3650 | 0.1898 | 0.2882 | 0.067* | |
C14 | 0.43570 (18) | 0.0996 (3) | 0.3343 (3) | 0.0702 (11) | |
H14A | 0.4669 | 0.1329 | 0.3324 | 0.084* | |
C15 | 0.45130 (17) | 0.0186 (2) | 0.3634 (3) | 0.0636 (10) | |
H15A | 0.4926 | −0.0032 | 0.3811 | 0.076* | |
C16 | 0.40397 (15) | −0.0317 (2) | 0.3663 (2) | 0.0469 (8) | |
C17 | 0.41534 (17) | −0.1161 (2) | 0.3965 (3) | 0.0593 (9) | |
H17A | 0.4567 | −0.1405 | 0.4191 | 0.071* | |
C18 | 0.36608 (17) | −0.1613 (2) | 0.3926 (3) | 0.0583 (9) | |
H18A | 0.3734 | −0.2172 | 0.4106 | 0.070* | |
C19 | 0.30353 (16) | −0.12441 (19) | 0.3612 (2) | 0.0469 (8) | |
C20 | 0.25091 (19) | −0.1774 (2) | 0.3593 (3) | 0.0709 (11) | |
H20A | 0.2102 | −0.1760 | 0.2921 | 0.106* | |
H20B | 0.2421 | −0.1564 | 0.4081 | 0.106* | |
H20C | 0.2668 | −0.2336 | 0.3766 | 0.106* | |
C21 | 0.09568 (13) | −0.05858 (15) | 0.1188 (2) | 0.0300 (6) | |
C22 | 0.10259 (13) | −0.07881 (16) | 0.2131 (2) | 0.0326 (6) | |
C23 | 0.06036 (14) | −0.13837 (18) | 0.2113 (2) | 0.0429 (7) | |
H23A | 0.0646 | −0.1533 | 0.2719 | 0.051* | |
C24 | 0.01104 (15) | −0.17676 (18) | 0.1192 (3) | 0.0464 (8) | |
H24A | −0.0170 | −0.2165 | 0.1201 | 0.056* | |
C25 | 0.00300 (15) | −0.15718 (18) | 0.0275 (2) | 0.0451 (7) | |
H25A | −0.0304 | −0.1828 | −0.0327 | 0.054* | |
C26 | 0.04579 (13) | −0.09809 (17) | 0.0262 (2) | 0.0353 (6) | |
C27 | 0.04210 (15) | −0.07264 (18) | −0.0633 (2) | 0.0437 (7) | |
H27A | 0.0103 | −0.0963 | −0.1262 | 0.052* | |
C28 | 0.08503 (15) | −0.01364 (18) | −0.0573 (2) | 0.0418 (7) | |
H28A | 0.0828 | 0.0022 | −0.1161 | 0.050* | |
C29 | 0.13316 (14) | 0.02407 (17) | 0.0377 (2) | 0.0343 (6) | |
C30 | 0.17693 (17) | 0.0923 (2) | 0.0415 (2) | 0.0522 (8) | |
H30A | 0.2234 | 0.0784 | 0.0901 | 0.078* | |
H30B | 0.1664 | 0.1431 | 0.0619 | 0.078* | |
H30C | 0.1693 | 0.0993 | −0.0249 | 0.078* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe | 0.0355 (2) | 0.0339 (2) | 0.0261 (2) | −0.00149 (17) | 0.01408 (18) | −0.00396 (17) |
O1 | 0.0433 (11) | 0.0450 (12) | 0.0265 (10) | 0.0090 (9) | 0.0146 (9) | −0.0055 (9) |
O2 | 0.0437 (11) | 0.0426 (11) | 0.0279 (10) | −0.0059 (9) | 0.0198 (9) | −0.0037 (8) |
O3 | 0.0413 (11) | 0.0343 (11) | 0.0440 (12) | −0.0009 (9) | 0.0213 (10) | −0.0017 (9) |
N1 | 0.0363 (12) | 0.0343 (13) | 0.0263 (12) | −0.0063 (10) | 0.0120 (11) | −0.0045 (10) |
N2 | 0.0340 (12) | 0.0295 (12) | 0.0282 (11) | 0.0006 (9) | 0.0175 (10) | −0.0027 (10) |
N3 | 0.0376 (13) | 0.0348 (13) | 0.0318 (13) | −0.0012 (10) | 0.0166 (11) | −0.0043 (10) |
C1 | 0.0350 (14) | 0.0351 (15) | 0.0309 (15) | −0.0119 (12) | 0.0183 (13) | −0.0070 (12) |
C2 | 0.0323 (14) | 0.0345 (15) | 0.0304 (15) | −0.0056 (11) | 0.0152 (12) | −0.0072 (12) |
C3 | 0.0368 (16) | 0.0479 (18) | 0.0404 (17) | −0.0018 (14) | 0.0164 (14) | −0.0105 (14) |
C4 | 0.0418 (17) | 0.051 (2) | 0.061 (2) | −0.0037 (15) | 0.0285 (17) | −0.0189 (16) |
C5 | 0.0528 (19) | 0.054 (2) | 0.052 (2) | −0.0145 (16) | 0.0350 (18) | −0.0224 (17) |
C6 | 0.0456 (17) | 0.0401 (16) | 0.0368 (16) | −0.0166 (13) | 0.0258 (14) | −0.0139 (13) |
C7 | 0.067 (2) | 0.054 (2) | 0.0344 (17) | −0.0181 (17) | 0.0322 (17) | −0.0123 (15) |
C8 | 0.059 (2) | 0.055 (2) | 0.0253 (15) | −0.0154 (16) | 0.0172 (15) | −0.0043 (14) |
C9 | 0.0463 (17) | 0.0417 (16) | 0.0259 (15) | −0.0099 (14) | 0.0140 (14) | −0.0013 (13) |
C10 | 0.062 (2) | 0.059 (2) | 0.0343 (18) | 0.0093 (18) | 0.0113 (16) | 0.0050 (16) |
C11 | 0.0380 (15) | 0.0391 (16) | 0.0262 (14) | −0.0030 (13) | 0.0125 (13) | −0.0096 (12) |
C12 | 0.0401 (16) | 0.0414 (16) | 0.0310 (15) | −0.0065 (13) | 0.0168 (14) | −0.0092 (13) |
C13 | 0.052 (2) | 0.050 (2) | 0.063 (2) | −0.0129 (16) | 0.0303 (18) | −0.0065 (17) |
C14 | 0.049 (2) | 0.077 (3) | 0.087 (3) | −0.0187 (19) | 0.038 (2) | −0.008 (2) |
C15 | 0.0379 (18) | 0.075 (3) | 0.066 (2) | −0.0042 (18) | 0.0214 (18) | −0.016 (2) |
C16 | 0.0386 (16) | 0.054 (2) | 0.0366 (17) | 0.0011 (14) | 0.0138 (14) | −0.0111 (14) |
C17 | 0.0454 (19) | 0.064 (2) | 0.051 (2) | 0.0170 (17) | 0.0156 (17) | −0.0038 (18) |
C18 | 0.058 (2) | 0.0441 (19) | 0.060 (2) | 0.0130 (17) | 0.0244 (19) | 0.0063 (17) |
C19 | 0.0529 (19) | 0.0400 (18) | 0.0422 (18) | 0.0039 (14) | 0.0227 (16) | −0.0016 (14) |
C20 | 0.075 (3) | 0.043 (2) | 0.096 (3) | 0.0009 (18) | 0.049 (3) | 0.006 (2) |
C21 | 0.0312 (13) | 0.0283 (14) | 0.0296 (14) | 0.0027 (11) | 0.0162 (12) | −0.0022 (11) |
C22 | 0.0348 (14) | 0.0306 (13) | 0.0319 (15) | −0.0003 (12) | 0.0181 (13) | −0.0018 (12) |
C23 | 0.0466 (17) | 0.0435 (17) | 0.0448 (18) | −0.0022 (14) | 0.0292 (16) | 0.0023 (14) |
C24 | 0.0446 (17) | 0.0375 (17) | 0.060 (2) | −0.0115 (13) | 0.0305 (17) | −0.0067 (15) |
C25 | 0.0421 (17) | 0.0422 (17) | 0.0441 (18) | −0.0092 (14) | 0.0195 (15) | −0.0150 (14) |
C26 | 0.0367 (15) | 0.0318 (15) | 0.0354 (15) | 0.0007 (12) | 0.0186 (13) | −0.0087 (12) |
C27 | 0.0495 (18) | 0.0437 (17) | 0.0295 (15) | 0.0009 (14) | 0.0165 (14) | −0.0106 (13) |
C28 | 0.0541 (18) | 0.0418 (17) | 0.0299 (15) | 0.0070 (14) | 0.0235 (15) | −0.0019 (13) |
C29 | 0.0432 (16) | 0.0326 (14) | 0.0313 (15) | 0.0058 (12) | 0.0233 (14) | −0.0001 (12) |
C30 | 0.066 (2) | 0.050 (2) | 0.0468 (19) | −0.0103 (16) | 0.0357 (18) | 0.0005 (16) |
Fe—O3 | 1.934 (2) | C12—C13 | 1.379 (4) |
Fe—O1 | 1.939 (2) | C13—C14 | 1.405 (5) |
Fe—O2 | 1.947 (2) | C13—H13A | 0.9300 |
Fe—N2 | 2.204 (2) | C14—C15 | 1.363 (5) |
Fe—N1 | 2.220 (2) | C14—H14A | 0.9300 |
Fe—N3 | 2.405 (2) | C15—C16 | 1.408 (5) |
O1—C2 | 1.324 (3) | C15—H15A | 0.9300 |
O2—C22 | 1.335 (3) | C16—C17 | 1.414 (5) |
O3—C12 | 1.319 (3) | C17—C18 | 1.352 (5) |
N1—C9 | 1.337 (3) | C17—H17A | 0.9300 |
N1—C1 | 1.371 (3) | C18—C19 | 1.416 (4) |
N2—C29 | 1.341 (3) | C18—H18A | 0.9300 |
N2—C21 | 1.369 (3) | C19—C20 | 1.503 (4) |
N3—C19 | 1.334 (4) | C20—H20A | 0.9600 |
N3—C11 | 1.374 (3) | C20—H20B | 0.9600 |
C1—C6 | 1.430 (3) | C20—H20C | 0.9600 |
C1—C2 | 1.434 (4) | C21—C26 | 1.420 (4) |
C2—C3 | 1.377 (4) | C21—C22 | 1.433 (4) |
C3—C4 | 1.415 (4) | C22—C23 | 1.378 (4) |
C3—H3A | 0.9300 | C23—C24 | 1.404 (4) |
C4—C5 | 1.353 (4) | C23—H23A | 0.9300 |
C4—H4A | 0.9300 | C24—C25 | 1.377 (4) |
C5—C6 | 1.409 (4) | C24—H24A | 0.9300 |
C5—H5A | 0.9300 | C25—C26 | 1.402 (4) |
C6—C7 | 1.406 (4) | C25—H25A | 0.9300 |
C7—C8 | 1.351 (5) | C26—C27 | 1.418 (4) |
C7—H7A | 0.9300 | C27—C28 | 1.360 (4) |
C8—C9 | 1.417 (4) | C27—H27A | 0.9300 |
C8—H8A | 0.9300 | C28—C29 | 1.418 (4) |
C9—C10 | 1.490 (4) | C28—H28A | 0.9300 |
C10—H10A | 0.9600 | C29—C30 | 1.492 (4) |
C10—H10B | 0.9600 | C30—H30A | 0.9600 |
C10—H10C | 0.9600 | C30—H30B | 0.9600 |
C11—C16 | 1.403 (4) | C30—H30C | 0.9600 |
C11—C12 | 1.439 (4) | ||
O3—Fe—O1 | 94.51 (8) | O3—C12—C13 | 123.5 (3) |
O3—Fe—O2 | 165.66 (8) | O3—C12—C11 | 118.9 (2) |
O1—Fe—O2 | 99.67 (8) | C13—C12—C11 | 117.6 (3) |
O3—Fe—N2 | 103.44 (8) | C12—C13—C14 | 121.2 (3) |
O1—Fe—N2 | 86.80 (8) | C12—C13—H13A | 119.4 |
O2—Fe—N2 | 79.69 (8) | C14—C13—H13A | 119.4 |
O3—Fe—N1 | 93.13 (8) | C15—C14—C13 | 121.7 (3) |
O1—Fe—N1 | 80.01 (8) | C15—C14—H14A | 119.1 |
O2—Fe—N1 | 87.20 (8) | C13—C14—H14A | 119.1 |
N2—Fe—N1 | 159.59 (8) | C14—C15—C16 | 119.0 (3) |
O3—Fe—N3 | 75.36 (8) | C14—C15—H15A | 120.5 |
O1—Fe—N3 | 169.70 (8) | C16—C15—H15A | 120.5 |
O2—Fe—N3 | 90.54 (8) | C11—C16—C15 | 120.2 (3) |
N2—Fe—N3 | 93.73 (8) | C11—C16—C17 | 116.2 (3) |
N1—Fe—N3 | 102.04 (8) | C15—C16—C17 | 123.6 (3) |
C2—O1—Fe | 117.27 (17) | C18—C17—C16 | 120.0 (3) |
C22—O2—Fe | 117.16 (16) | C18—C17—H17A | 120.0 |
C12—O3—Fe | 123.2 (2) | C16—C17—H17A | 120.0 |
C9—N1—C1 | 118.5 (2) | C17—C18—C19 | 120.7 (3) |
C9—N1—Fe | 134.1 (2) | C17—C18—H18A | 119.7 |
C1—N1—Fe | 107.32 (16) | C19—C18—H18A | 119.7 |
C29—N2—C21 | 118.8 (2) | N3—C19—C18 | 121.2 (3) |
C29—N2—Fe | 132.35 (18) | N3—C19—C20 | 120.4 (3) |
C21—N2—Fe | 108.49 (16) | C18—C19—C20 | 118.4 (3) |
C19—N3—C11 | 118.0 (2) | C19—C20—H20A | 109.5 |
C19—N3—Fe | 135.3 (2) | C19—C20—H20B | 109.5 |
C11—N3—Fe | 106.7 (2) | H20A—C20—H20B | 109.5 |
N1—C1—C6 | 123.3 (3) | C19—C20—H20C | 109.5 |
N1—C1—C2 | 116.7 (2) | H20A—C20—H20C | 109.5 |
C6—C1—C2 | 120.0 (3) | H20B—C20—H20C | 109.5 |
O1—C2—C3 | 123.3 (3) | N2—C21—C26 | 123.4 (2) |
O1—C2—C1 | 118.5 (2) | N2—C21—C22 | 116.1 (2) |
C3—C2—C1 | 118.2 (2) | C26—C21—C22 | 120.5 (2) |
C2—C3—C4 | 121.1 (3) | O2—C22—C23 | 123.7 (3) |
C2—C3—H3A | 119.5 | O2—C22—C21 | 118.2 (2) |
C4—C3—H3A | 119.5 | C23—C22—C21 | 118.1 (2) |
C5—C4—C3 | 121.4 (3) | C22—C23—C24 | 120.9 (3) |
C5—C4—H4A | 119.3 | C22—C23—H23A | 119.6 |
C3—C4—H4A | 119.3 | C24—C23—H23A | 119.6 |
C4—C5—C6 | 120.2 (3) | C25—C24—C23 | 121.8 (3) |
C4—C5—H5A | 119.9 | C25—C24—H24A | 119.1 |
C6—C5—H5A | 119.9 | C23—C24—H24A | 119.1 |
C7—C6—C5 | 125.0 (3) | C24—C25—C26 | 119.2 (3) |
C7—C6—C1 | 116.0 (3) | C24—C25—H25A | 120.4 |
C5—C6—C1 | 119.1 (3) | C26—C25—H25A | 120.4 |
C8—C7—C6 | 120.2 (3) | C25—C26—C27 | 124.3 (3) |
C8—C7—H7A | 119.9 | C25—C26—C21 | 119.5 (3) |
C6—C7—H7A | 119.9 | C27—C26—C21 | 116.2 (2) |
C7—C8—C9 | 121.4 (3) | C28—C27—C26 | 120.0 (3) |
C7—C8—H8A | 119.3 | C28—C27—H27A | 120.0 |
C9—C8—H8A | 119.3 | C26—C27—H27A | 120.0 |
N1—C9—C8 | 120.6 (3) | C27—C28—C29 | 120.8 (3) |
N1—C9—C10 | 119.3 (3) | C27—C28—H28A | 119.6 |
C8—C9—C10 | 120.0 (3) | C29—C28—H28A | 119.6 |
C9—C10—H10A | 109.5 | N2—C29—C28 | 120.8 (3) |
C9—C10—H10B | 109.5 | N2—C29—C30 | 119.3 (2) |
H10A—C10—H10B | 109.5 | C28—C29—C30 | 119.9 (3) |
C9—C10—H10C | 109.5 | C29—C30—H30A | 109.5 |
H10A—C10—H10C | 109.5 | C29—C30—H30B | 109.5 |
H10B—C10—H10C | 109.5 | H30A—C30—H30B | 109.5 |
N3—C11—C16 | 123.9 (3) | C29—C30—H30C | 109.5 |
N3—C11—C12 | 115.9 (2) | H30A—C30—H30C | 109.5 |
C16—C11—C12 | 120.2 (3) | H30B—C30—H30C | 109.5 |
O3—Fe—O1—C2 | −96.42 (19) | C1—C6—C7—C8 | −0.1 (4) |
O2—Fe—O1—C2 | 81.37 (19) | C6—C7—C8—C9 | −0.4 (5) |
N2—Fe—O1—C2 | 160.34 (19) | C1—N1—C9—C8 | −0.1 (4) |
N1—Fe—O1—C2 | −4.03 (18) | Fe—N1—C9—C8 | −179.0 (2) |
N3—Fe—O1—C2 | −106.4 (4) | C1—N1—C9—C10 | −178.9 (3) |
O3—Fe—O2—C22 | −108.7 (3) | Fe—N1—C9—C10 | 2.2 (4) |
O1—Fe—O2—C22 | 80.25 (18) | C7—C8—C9—N1 | 0.5 (4) |
N2—Fe—O2—C22 | −4.67 (18) | C7—C8—C9—C10 | 179.3 (3) |
N1—Fe—O2—C22 | 159.61 (18) | C19—N3—C11—C16 | −0.1 (4) |
N3—Fe—O2—C22 | −98.36 (18) | Fe—N3—C11—C16 | 178.3 (2) |
O1—Fe—O3—C12 | −177.9 (2) | C19—N3—C11—C12 | −179.3 (2) |
O2—Fe—O3—C12 | 11.0 (4) | Fe—N3—C11—C12 | −0.9 (3) |
N2—Fe—O3—C12 | −90.1 (2) | Fe—O3—C12—C13 | 178.7 (2) |
N1—Fe—O3—C12 | 101.9 (2) | Fe—O3—C12—C11 | −0.9 (3) |
N3—Fe—O3—C12 | 0.3 (2) | N3—C11—C12—O3 | 1.2 (4) |
O3—Fe—N1—C9 | −83.5 (3) | C16—C11—C12—O3 | −178.0 (3) |
O1—Fe—N1—C9 | −177.5 (3) | N3—C11—C12—C13 | −178.4 (3) |
O2—Fe—N1—C9 | 82.1 (3) | C16—C11—C12—C13 | 2.3 (4) |
N2—Fe—N1—C9 | 132.0 (3) | O3—C12—C13—C14 | 179.8 (3) |
N3—Fe—N1—C9 | −7.8 (3) | C11—C12—C13—C14 | −0.5 (5) |
O3—Fe—N1—C1 | 97.54 (16) | C12—C13—C14—C15 | −0.6 (6) |
O1—Fe—N1—C1 | 3.51 (16) | C13—C14—C15—C16 | −0.1 (6) |
O2—Fe—N1—C1 | −96.82 (16) | N3—C11—C16—C15 | 177.8 (3) |
N2—Fe—N1—C1 | −47.0 (3) | C12—C11—C16—C15 | −3.0 (4) |
N3—Fe—N1—C1 | 173.23 (16) | N3—C11—C16—C17 | −1.2 (4) |
O3—Fe—N2—C29 | −17.2 (2) | C12—C11—C16—C17 | 178.0 (3) |
O1—Fe—N2—C29 | 76.7 (2) | C14—C15—C16—C11 | 1.9 (5) |
O2—Fe—N2—C29 | 177.2 (2) | C14—C15—C16—C17 | −179.2 (3) |
N1—Fe—N2—C29 | 126.3 (3) | C11—C16—C17—C18 | 2.1 (5) |
N3—Fe—N2—C29 | −93.0 (2) | C15—C16—C17—C18 | −176.8 (3) |
O3—Fe—N2—C21 | 170.47 (15) | C16—C17—C18—C19 | −1.8 (5) |
O1—Fe—N2—C21 | −95.66 (16) | C11—N3—C19—C18 | 0.4 (4) |
O2—Fe—N2—C21 | 4.78 (16) | Fe—N3—C19—C18 | −177.4 (2) |
N1—Fe—N2—C21 | −46.1 (3) | C11—N3—C19—C20 | −179.7 (3) |
N3—Fe—N2—C21 | 94.65 (16) | Fe—N3—C19—C20 | 2.5 (5) |
O3—Fe—N3—C19 | 178.4 (3) | C17—C18—C19—N3 | 0.5 (5) |
O1—Fe—N3—C19 | −171.3 (4) | C17—C18—C19—C20 | −179.3 (3) |
O2—Fe—N3—C19 | 1.0 (3) | C29—N2—C21—C26 | 1.3 (4) |
N2—Fe—N3—C19 | −78.7 (3) | Fe—N2—C21—C26 | 174.9 (2) |
N1—Fe—N3—C19 | 88.3 (3) | C29—N2—C21—C22 | −177.8 (2) |
O3—Fe—N3—C11 | 0.37 (16) | Fe—N2—C21—C22 | −4.3 (3) |
O1—Fe—N3—C11 | 10.7 (5) | Fe—O2—C22—C23 | −175.5 (2) |
O2—Fe—N3—C11 | −177.00 (17) | Fe—O2—C22—C21 | 3.9 (3) |
N2—Fe—N3—C11 | 103.29 (17) | N2—C21—C22—O2 | 0.8 (3) |
N1—Fe—N3—C11 | −89.74 (17) | C26—C21—C22—O2 | −178.3 (2) |
C9—N1—C1—C6 | −0.4 (4) | N2—C21—C22—C23 | −179.8 (2) |
Fe—N1—C1—C6 | 178.8 (2) | C26—C21—C22—C23 | 1.1 (4) |
C9—N1—C1—C2 | 178.2 (2) | O2—C22—C23—C24 | 178.0 (3) |
Fe—N1—C1—C2 | −2.6 (3) | C21—C22—C23—C24 | −1.4 (4) |
Fe—O1—C2—C3 | −176.5 (2) | C22—C23—C24—C25 | 0.4 (5) |
Fe—O1—C2—C1 | 3.9 (3) | C23—C24—C25—C26 | 0.9 (4) |
N1—C1—C2—O1 | −0.4 (4) | C24—C25—C26—C27 | −179.7 (3) |
C6—C1—C2—O1 | 178.2 (2) | C24—C25—C26—C21 | −1.1 (4) |
N1—C1—C2—C3 | 179.9 (2) | N2—C21—C26—C25 | −178.9 (2) |
C6—C1—C2—C3 | −1.4 (4) | C22—C21—C26—C25 | 0.1 (4) |
O1—C2—C3—C4 | −178.4 (3) | N2—C21—C26—C27 | −0.3 (4) |
C1—C2—C3—C4 | 1.2 (4) | C22—C21—C26—C27 | 178.8 (2) |
C2—C3—C4—C5 | −0.4 (5) | C25—C26—C27—C28 | 178.7 (3) |
C3—C4—C5—C6 | −0.2 (5) | C21—C26—C27—C28 | 0.1 (4) |
C4—C5—C6—C7 | 178.8 (3) | C26—C27—C28—C29 | −1.0 (4) |
C4—C5—C6—C1 | 0.1 (4) | C21—N2—C29—C28 | −2.1 (4) |
N1—C1—C6—C7 | 0.5 (4) | Fe—N2—C29—C28 | −173.85 (19) |
C2—C1—C6—C7 | −178.0 (2) | C21—N2—C29—C30 | 176.2 (2) |
N1—C1—C6—C5 | 179.4 (2) | Fe—N2—C29—C30 | 4.5 (4) |
C2—C1—C6—C5 | 0.8 (4) | C27—C28—C29—N2 | 2.0 (4) |
C5—C6—C7—C8 | −178.9 (3) | C27—C28—C29—C30 | −176.3 (3) |
[Cu(C10H8NO)2(H2O)] | Dx = 1.549 Mg m−3 |
Mr = 397.90 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbcn | Cell parameters from 3814 reflections |
a = 7.5388 (2) Å | θ = 1.6–28.4° |
b = 9.1091 (1) Å | µ = 1.30 mm−1 |
c = 24.8514 (6) Å | T = 293 K |
V = 1706.59 (6) Å3 | Rectangular slab, orange |
Z = 4 | 0.34 × 0.16 × 0.06 mm |
F(000) = 820 |
Siemens SMART CCD area detector diffractometer | 1500 independent reflections |
Radiation source: fine-focus sealed tube | 1056 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.119 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 1.6° |
ω scans | h = −8→8 |
Absorption correction: empirical (using intensity measurements) (SADABS, Sheldrick, 1996) | k = −10→7 |
Tmin = 0.666, Tmax = 0.926 | l = −29→26 |
8856 measured reflections |
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)] = 0.088 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.239 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.1587P)2] where P = (Fo2 + 2Fc2)/3 |
1500 reflections | (Δ/σ)max < 0.001 |
104 parameters | Δρmax = 1.84 e Å−3 |
0 restraints | Δρmin = −1.52 e Å−3 |
[Cu(C10H8NO)2(H2O)] | V = 1706.59 (6) Å3 |
Mr = 397.90 | Z = 4 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 7.5388 (2) Å | µ = 1.30 mm−1 |
b = 9.1091 (1) Å | T = 293 K |
c = 24.8514 (6) Å | 0.34 × 0.16 × 0.06 mm |
Siemens SMART CCD area detector diffractometer | 1500 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS, Sheldrick, 1996) | 1056 reflections with I > 2σ(I) |
Tmin = 0.666, Tmax = 0.926 | Rint = 0.119 |
8856 measured reflections |
R[F2 > 2σ(F2)] = 0.088 | 0 restraints |
wR(F2) = 0.239 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 1.84 e Å−3 |
1500 reflections | Δρmin = −1.52 e Å−3 |
104 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 | ||
Cu | 0.0000 | 0.19579 (11) | 0.2500 | 0.0207 (5) | |
O1 | −0.2170 (5) | 0.1121 (5) | 0.28387 (15) | 0.0241 (7) | |
O1W | 0.0000 | 0.4453 (7) | 0.2500 | 0.0241 (7) | |
H1W1 | −0.0912 | 0.4753 | 0.2642 | 0.036* | |
N1 | 0.0870 (7) | 0.2030 (5) | 0.3267 (2) | 0.0241 (7) | |
C1 | −0.0411 (8) | 0.1500 (7) | 0.3612 (3) | 0.0241 (7) | |
C2 | −0.2016 (7) | 0.1002 (7) | 0.3374 (2) | 0.0230 (13) | |
C3 | −0.3306 (8) | 0.0411 (8) | 0.3702 (2) | 0.0338 (17) | |
H3A | −0.4352 | 0.0047 | 0.3555 | 0.041* | |
C4 | −0.3030 (9) | 0.0360 (8) | 0.4267 (2) | 0.0386 (18) | |
H4A | −0.3915 | −0.0033 | 0.4484 | 0.046* | |
C5 | −0.1539 (9) | 0.0858 (9) | 0.4500 (2) | 0.0372 (18) | |
H5A | −0.1409 | 0.0813 | 0.4872 | 0.045* | |
C6 | −0.0170 (8) | 0.1451 (8) | 0.4177 (3) | 0.0279 (16) | |
C7 | 0.1463 (10) | 0.2021 (9) | 0.4373 (3) | 0.0391 (19) | |
H7A | 0.1691 | 0.2026 | 0.4741 | 0.047* | |
C8 | 0.2676 (9) | 0.2552 (8) | 0.4029 (3) | 0.0360 (17) | |
H8A | 0.3730 | 0.2933 | 0.4164 | 0.043* | |
C9 | 0.2395 (8) | 0.2547 (7) | 0.3466 (2) | 0.0251 (14) | |
C10 | 0.3746 (9) | 0.3150 (8) | 0.3083 (3) | 0.0372 (18) | |
H10A | 0.3313 | 0.3064 | 0.2721 | 0.056* | |
H10B | 0.4832 | 0.2608 | 0.3118 | 0.056* | |
H10C | 0.3959 | 0.4165 | 0.3164 | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu | 0.0254 (7) | 0.0105 (7) | 0.0262 (7) | 0.000 | 0.0005 (4) | 0.000 |
O1 | 0.0297 (15) | 0.0077 (14) | 0.0348 (15) | 0.0002 (12) | 0.0020 (11) | −0.0004 (13) |
O1W | 0.0297 (15) | 0.0077 (14) | 0.0348 (15) | 0.0002 (12) | 0.0020 (11) | −0.0004 (13) |
N1 | 0.0297 (15) | 0.0077 (14) | 0.0348 (15) | 0.0002 (12) | 0.0020 (11) | −0.0004 (13) |
C1 | 0.0297 (15) | 0.0077 (14) | 0.0348 (15) | 0.0002 (12) | 0.0020 (11) | −0.0004 (13) |
C2 | 0.028 (3) | 0.008 (3) | 0.033 (3) | 0.003 (3) | 0.001 (2) | −0.001 (3) |
C3 | 0.034 (4) | 0.025 (4) | 0.043 (4) | −0.007 (3) | 0.002 (3) | 0.003 (3) |
C4 | 0.047 (4) | 0.030 (5) | 0.038 (4) | −0.006 (3) | 0.011 (3) | 0.013 (3) |
C5 | 0.047 (4) | 0.037 (5) | 0.027 (3) | 0.002 (4) | 0.004 (3) | 0.004 (3) |
C6 | 0.039 (4) | 0.017 (4) | 0.028 (3) | 0.003 (3) | −0.001 (3) | −0.001 (3) |
C7 | 0.050 (5) | 0.036 (5) | 0.031 (4) | 0.000 (4) | −0.007 (3) | −0.004 (3) |
C8 | 0.035 (4) | 0.022 (4) | 0.051 (4) | −0.007 (3) | −0.011 (3) | −0.005 (3) |
C9 | 0.028 (3) | 0.006 (3) | 0.041 (4) | 0.004 (3) | −0.001 (3) | −0.003 (3) |
C10 | 0.033 (4) | 0.023 (4) | 0.055 (4) | −0.009 (3) | −0.004 (3) | −0.005 (3) |
Cu—O1i | 1.991 (4) | C4—C5 | 1.343 (9) |
Cu—O1 | 1.991 (4) | C4—H4A | 0.9300 |
Cu—N1 | 2.018 (5) | C5—C6 | 1.415 (9) |
Cu—N1i | 2.018 (5) | C5—H5A | 0.9300 |
Cu—O1W | 2.273 (6) | C6—C7 | 1.421 (9) |
O1—C2 | 1.339 (7) | C7—C8 | 1.342 (10) |
O1W—H1W1 | 0.8200 | C7—H7A | 0.9300 |
N1—C9 | 1.336 (8) | C8—C9 | 1.417 (8) |
N1—C1 | 1.377 (8) | C8—H8A | 0.9300 |
C1—C6 | 1.418 (9) | C9—C10 | 1.498 (9) |
C1—C2 | 1.422 (9) | C10—H10A | 0.9600 |
C2—C3 | 1.380 (8) | C10—H10B | 0.9600 |
C3—C4 | 1.418 (8) | C10—H10C | 0.9600 |
C3—H3A | 0.9300 | ||
O1i—Cu—O1 | 135.0 (2) | C5—C4—C3 | 122.6 (6) |
O1i—Cu—N1 | 98.4 (2) | C5—C4—H4A | 118.7 |
O1—Cu—N1 | 83.1 (2) | C3—C4—H4A | 118.7 |
O1i—Cu—N1i | 83.1 (2) | C4—C5—C6 | 119.7 (6) |
O1—Cu—N1i | 98.4 (2) | C4—C5—H5A | 120.2 |
N1—Cu—N1i | 176.2 (3) | C6—C5—H5A | 120.2 |
O1i—Cu—O1W | 112.5 (1) | C5—C6—C1 | 118.7 (6) |
O1—Cu—O1W | 112.50 (12) | C5—C6—C7 | 125.3 (6) |
N1—Cu—O1W | 88.12 (14) | C1—C6—C7 | 116.0 (6) |
N1i—Cu—O1W | 88.1 (1) | C8—C7—C6 | 120.2 (6) |
C2—O1—Cu | 112.3 (3) | C8—C7—H7A | 119.9 |
Cu—O1W—H1W1 | 109.5 | C6—C7—H7A | 119.9 |
C9—N1—C1 | 119.8 (6) | C7—C8—C9 | 121.8 (6) |
C9—N1—Cu | 129.8 (4) | C7—C8—H8A | 119.1 |
C1—N1—Cu | 110.4 (4) | C9—C8—H8A | 119.1 |
N1—C1—C6 | 122.5 (6) | N1—C9—C8 | 119.6 (6) |
N1—C1—C2 | 116.7 (6) | N1—C9—C10 | 118.7 (5) |
C6—C1—C2 | 120.8 (6) | C8—C9—C10 | 121.6 (6) |
O1—C2—C3 | 124.0 (6) | C9—C10—H10A | 109.5 |
O1—C2—C1 | 117.4 (5) | C9—C10—H10B | 109.5 |
C3—C2—C1 | 118.6 (6) | H10A—C10—H10B | 109.5 |
C2—C3—C4 | 119.6 (6) | C9—C10—H10C | 109.5 |
C2—C3—H3A | 120.2 | H10A—C10—H10C | 109.5 |
C4—C3—H3A | 120.2 | H10B—C10—H10C | 109.5 |
O1i—Cu—O1—C2 | 94.3 (4) | O1—C2—C3—C4 | −178.8 (6) |
N1—Cu—O1—C2 | −0.6 (4) | C1—C2—C3—C4 | 2.1 (9) |
N1i—Cu—O1—C2 | −177.1 (4) | C2—C3—C4—C5 | −0.6 (11) |
O1W—Cu—O1—C2 | −85.7 (4) | C3—C4—C5—C6 | −0.4 (12) |
O1i—Cu—N1—C9 | 48.0 (5) | C4—C5—C6—C1 | −0.2 (11) |
O1—Cu—N1—C9 | −177.4 (5) | C4—C5—C6—C7 | 179.6 (8) |
O1W—Cu—N1—C9 | −64.5 (5) | N1—C1—C6—C5 | −178.6 (6) |
O1i—Cu—N1—C1 | −134.8 (4) | C2—C1—C6—C5 | 1.8 (10) |
O1—Cu—N1—C1 | −0.2 (4) | N1—C1—C6—C7 | 1.6 (10) |
O1W—Cu—N1—C1 | 112.7 (4) | C2—C1—C6—C7 | −178.0 (6) |
C9—N1—C1—C6 | −1.2 (9) | C5—C6—C7—C8 | 179.6 (7) |
Cu—N1—C1—C6 | −178.7 (5) | C1—C6—C7—C8 | −0.6 (11) |
C9—N1—C1—C2 | 178.5 (5) | C6—C7—C8—C9 | −0.9 (11) |
Cu—N1—C1—C2 | 1.0 (7) | C1—N1—C9—C8 | −0.3 (9) |
Cu—O1—C2—C3 | −177.8 (5) | Cu—N1—C9—C8 | 176.6 (5) |
Cu—O1—C2—C1 | 1.3 (7) | C1—N1—C9—C10 | −178.5 (6) |
N1—C1—C2—O1 | −1.6 (8) | Cu—N1—C9—C10 | −1.6 (9) |
C6—C1—C2—O1 | 178.1 (5) | C7—C8—C9—N1 | 1.4 (10) |
N1—C1—C2—C3 | 177.6 (6) | C7—C8—C9—C10 | 179.5 (7) |
C6—C1—C2—C3 | −2.7 (9) |
Symmetry code: (i) −x, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O1ii | 0.82 | 1.97 | 2.752 (5) | 159 |
Symmetry code: (ii) −x−1/2, y+1/2, z. |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | [Fe(C10H8NO)3] | [Cu(C10H8NO)2(H2O)] |
Mr | 530.37 | 397.90 |
Crystal system, space group | Monoclinic, C2/c | Orthorhombic, Pbcn |
Temperature (K) | 293 | 293 |
a, b, c (Å) | 23.8220 (3), 16.0839 (3), 15.6819 (3) | 7.5388 (2), 9.1091 (1), 24.8514 (6) |
α, β, γ (°) | 90, 123.571 (1), 90 | 90, 90, 90 |
V (Å3) | 5006.31 (15) | 1706.59 (6) |
Z | 8 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.64 | 1.30 |
Crystal size (mm) | 0.48 × 0.40 × 0.08 | 0.34 × 0.16 × 0.06 |
Data collection | ||
Diffractometer | Siemens SMART CCD area detector diffractometer | Siemens SMART CCD area detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | Empirical (using intensity measurements) (SADABS, Sheldrick, 1996) |
Tmin, Tmax | 0.749, 0.951 | 0.666, 0.926 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16629, 5734, 3729 | 8856, 1500, 1056 |
Rint | 0.072 | 0.119 |
(sin θ/λ)max (Å−1) | 0.650 | 0.594 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.142, 0.94 | 0.088, 0.239, 1.07 |
No. of reflections | 5734 | 1500 |
No. of parameters | 337 | 104 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.45, −0.96 | 1.84, −1.52 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT and SADABS (Sheldrick, 1996), SHELXTL (Sheldrick, 1997), SHELXTL and PLATON (Spek, 1990).
Fe—O3 | 1.934 (2) | Fe—N2 | 2.204 (2) |
Fe—O1 | 1.939 (2) | Fe—N1 | 2.220 (2) |
Fe—O2 | 1.947 (2) | Fe—N3 | 2.405 (2) |
O3—Fe—O1 | 94.51 (8) | O1—Fe—N1 | 80.01 (8) |
O1—Fe—O2 | 99.67 (8) | O2—Fe—N1 | 87.20 (8) |
O1—Fe—N2 | 86.80 (8) | O3—Fe—N3 | 75.36 (8) |
O2—Fe—N2 | 79.69 (8) | C12—O3—Fe | 123.2 (2) |
O3—Fe—N1 | 93.13 (8) | C11—N3—Fe | 106.7 (2) |
Cu—O1i | 1.991 (4) | Cu—N1i | 2.018 (5) |
Cu—O1 | 1.991 (4) | Cu—O1W | 2.273 (6) |
Cu—N1 | 2.018 (5) | ||
O1i—Cu—N1 | 98.4 (2) | O1—Cu—N1i | 98.4 (2) |
O1—Cu—N1 | 83.1 (2) | O1i—Cu—O1W | 112.5 (1) |
O1i—Cu—N1i | 83.1 (2) | N1i—Cu—O1W | 88.1 (1) |
Symmetry code: (i) −x, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O1ii | 0.82 | 1.970 | 2.752 (5) | 159 |
Symmetry code: (ii) −x−1/2, y+1/2, z. |
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8-Quinolinol and its substituted analogues have been widely used as an extracting agent for transition metals and for the fluorescence analysis of 3 A group elements as well as in the preparation of non-linear optical materials with second harmonic generation at high intensity and stability at room temperature (Sanz-Medel et al., 1987; Sugiyama et al., 1991; Kato et al., 1988). Its complexes with transition metals have also found extensive applications. For example, bis(8-quinolinolato-N,O)nickel(II) has been used as a free-resistant additive for olefin polymers and as a fungicide for leather (Uma & Krishnamurthi, 1984). Also, tri(8-quinolinolato)cobalt(III) has been synthesized and used to assist in the metal-ligand assignments which are further based on Zn labelling of the Zn complex, and on the effects of metal ion substitution in relation to expectations based on crystal field theory (Nakamoto & Ohkaku, 1971). In this paper, we report the crystal structures of compounds (I) and (II). \sch
The molecular structures of compounds (I) and (II) are illustrated in Figs. 1 and 2, respectively. Selected bond lengths and angles are listed in Tables 1 and 2. In compound (I), the three 2-methyl-8-quinolinol ligands are coordinated to the central Fe atom by their oxygen and nitrogen atoms, forming five-membered chelate rings. The iron(III) atom has a slightly distorted octahedral configuration because of the result of the forced configuration of the five-membered chelate rings. Its structure is similar to that of tris(8-quinolinolate)chromium(III) (Folting et al., 1968) and tris(8-quinolinolate)manganese(III) (Xiong et al., 1995). The Fe—O bond distances in compound (I) are normal (Table 1), which are shorter than those in [Fe(OCH3)6(acac)4(N3)2] [1.986 (5) Å; Li et al. (1997)]. The Fe—N bond distances are in agreement with those in [Fe(phen)2(PhCOO)2]4+ [2.200 (4) Å; Li et al. (1995)]. Because of the methyl group steric effect, the Fe—N3 bond length is apparently longer than Fe—N1 and Fe—N2. Also, the chelate angle Fe—O3—C12 is the largest, Fe—N3—C11 being intermediate and the bite angle O3—Fe—N3 is the smallest.
In compound (II), the central pentacoordinated CuII atom and H2O group lie on a crystallographic twofold axis and its geometry is is close to trigonal bipyramidal. The basal coordination positions are occupied by three O atoms, and the apical positions are occupied by the two N atoms. The Cu—O1 and Cu—N1 distances fall within the normal range (Table 2), corresponding to the bond lengths in other five coordinative Cu complexes [Cu—O 1.910 (9)–1.997 (8) Å (Chen et al., 1997); Cu—N 1.979 (2)–2.029 (2) Å, (Liu et al., 1997); Cu—O 2.01 (1) Å and Cu—N 1.95–2.01 Å (Chen et al., 1995); Cu—O 1.942–1.958 Å and Cu—N 2.016–2.019 Å (Bu et al., 1990)]. The axial Cu—O1W bond, however, is significantly longer than the equatorial Cu—O1 bond, and is agreement with that found in a similar Cu—O1w bond compound (Liu et al., 1997). The five-membered chelate ring (Cu, O1, N1, C1 and C2) with 2-methyl-8-quinolinolate ligand are coplanar, with the maximum deviation of atoms being 0.039 (4) Å. The dihedral angle between the two quinolinolate ligand planes is 48.5 (1)°. The structure of CuO2N2 is obviously a distorted tetrahedron. The coordination plane composing of Cu, O1, O1i (i = -x, y, 1/2 - z) and O1W has a dihedral angle of 81.8 (2)° with the Cu, N1, N1i (i = -x, y, 1/2 - z) and O1W plane. They form a dihedral angle of 85.0 (2) and 66.9 (2)° with chelate ring plane, respectively.
For the compound (II), there is an intermolecular hydrogen bond, O1W—H···O1, with a separation of 2.752 (5) Å. This hydrogen bond links the molecules into a linear chain along the b axis.