Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048556/cf2152sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048556/cf2152Isup2.hkl |
CCDC reference: 1294011
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.054
- wR factor = 0.140
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT245_ALERT_2_B U(iso) H1W Smaller than U(eq) O1W by ... 0.05 AngSq PLAT245_ALERT_2_B U(iso) H2W Smaller than U(eq) O1W by ... 0.05 AngSq PLAT420_ALERT_2_B D-H Without Acceptor O1W - H2W ... ?
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for N4 - C16 .. 5.62 su PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT794_ALERT_5_G Check Predicted Bond Valency for Fe1 (3) 4.26 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
A mixture of iron trichloride (0.1 mmol) and 2-pyridinecarbonyl-8-aminoquinoline (0.2 mmol) in 25 ml me thanol was refluxed for 2 h and filtered. The filtrate was evaporated naturally in an open flask. Green crystals were obtained after one week in a yield of 12%. Anal. Calc. for C30H22ClFeN6O7: C 53.73, H 2.99, N 12.54%; Found: 53.68, H 3.02, N 12.51%.
The H atoms of the water molecule were located in a difference density map and were refined with distance restraints [H···H = 1.38 (2) Å and O—H = 0.82 (2) Å] and with Uiso(H) = 0.08 Å2. All other H atoms were placed in calculated positions with a C—H bond distance of 0.93 Å and Uiso(H) = 1.2Ueq(C).
Complexes containing carbonyl amine (organic amide) ligands have been the interest of chemists due to their potential applications, such as in catalysis, optics, information storage, medicine, molecular electrochemistry, biochemistry and biological pharmaceuticals (Li et al., 1993; Go et al., 2004). Thus far, N-containing aromatic carbonyl amines have been widely used in dye intermediates, organic synthesis, sensitization materials, functional pigments, adipiodone and acetrizoic acid (An et al., 2000). Pyridine carbonyl amine is also a good ligand in coordination chemistry due to its strong coordination ability and versatile coordination modes, so much attention has been paid to it in recent years (Baroni et al., 1996; Hundal et al., 2002). Here we report the new title complex.
The title compound contains an iron(III) cation chelated by two 2-pyridinecarbonyl-8-aminoquinoline ligands via six N atoms, exhibiting octahedral geometry around the central iron ion (Fig. 1). The Fe—N bond length are in the range 1.880 (3)–1.972 (3) Å. Each ligand is planar (r.m.s. deviations 0.0314 and 0.0282 Å). The dihedral angle between the two ligand planes is 86.55 (1)°. There is a weak intermolecular hydrogen bond between water and perchlorate, contributing to the packing.
For related literature, see: Li et al. (1993); Go et al. (2004); An et al. (2000); Baroni et al. (1996); Hundal et al. (2002).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).
Fig. 1. The asymmetric unit of the title structure, drawn with 30% probability displacement ellipsoids. |
[Fe(C15H10N3O)2]ClO4·H2O | Z = 2 |
Mr = 669.84 | F(000) = 686 |
Triclinic, P1 | Dx = 1.552 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2452 (10) Å | Cell parameters from 5559 reflections |
b = 11.944 (2) Å | θ = 3.1–26.0° |
c = 13.0523 (10) Å | µ = 0.68 mm−1 |
α = 95.807 (5)° | T = 293 K |
β = 90.462 (1)° | Block, green |
γ = 91.615 (5)° | 0.42 × 0.26 × 0.22 mm |
V = 1433.3 (3) Å3 |
Bruker APEXII CCD area-detector diffractometer | 5559 independent reflections |
Radiation source: fine-focus sealed tube | 3729 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
φ and ω scans | θmax = 26.0°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = 0→11 |
Tmin = 0.763, Tmax = 0.865 | k = −14→14 |
13425 measured reflections | l = −16→16 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.092P)2] where P = (Fo2 + 2Fc2)/3 |
5559 reflections | (Δ/σ)max < 0.001 |
413 parameters | Δρmax = 0.50 e Å−3 |
3 restraints | Δρmin = −0.42 e Å−3 |
[Fe(C15H10N3O)2]ClO4·H2O | γ = 91.615 (5)° |
Mr = 669.84 | V = 1433.3 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.2452 (10) Å | Mo Kα radiation |
b = 11.944 (2) Å | µ = 0.68 mm−1 |
c = 13.0523 (10) Å | T = 293 K |
α = 95.807 (5)° | 0.42 × 0.26 × 0.22 mm |
β = 90.462 (1)° |
Bruker APEXII CCD area-detector diffractometer | 5559 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 3729 reflections with I > 2σ(I) |
Tmin = 0.763, Tmax = 0.865 | Rint = 0.022 |
13425 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 3 restraints |
wR(F2) = 0.140 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.50 e Å−3 |
5559 reflections | Δρmin = −0.42 e Å−3 |
413 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 | ||
C1 | 0.7506 (5) | 0.3112 (4) | 0.3721 (3) | 0.0659 (10) | |
H1A | 0.7130 | 0.3810 | 0.3939 | 0.079* | |
C2 | 0.8893 (6) | 0.2844 (5) | 0.4060 (4) | 0.0892 (15) | |
H2A | 0.9414 | 0.3358 | 0.4515 | 0.107* | |
C3 | 0.9464 (5) | 0.1862 (5) | 0.3735 (4) | 0.0820 (13) | |
H3A | 1.0389 | 0.1704 | 0.3954 | 0.098* | |
C4 | 0.8682 (5) | 0.1051 (4) | 0.3056 (3) | 0.0654 (11) | |
C5 | 0.9158 (5) | −0.0009 (5) | 0.2647 (4) | 0.0792 (13) | |
H5A | 1.0073 | −0.0234 | 0.2826 | 0.095* | |
C6 | 0.8324 (6) | −0.0699 (4) | 0.2007 (4) | 0.0796 (14) | |
H6A | 0.8677 | −0.1392 | 0.1751 | 0.096* | |
C7 | 0.6920 (5) | −0.0408 (3) | 0.1706 (3) | 0.0628 (10) | |
H7A | 0.6361 | −0.0905 | 0.1261 | 0.075* | |
C8 | 0.6395 (4) | 0.0610 (3) | 0.2073 (3) | 0.0499 (8) | |
C9 | 0.7297 (4) | 0.1362 (3) | 0.2760 (3) | 0.0493 (8) | |
C10 | 0.3957 (4) | 0.0540 (3) | 0.1333 (3) | 0.0565 (9) | |
C11 | 0.2748 (4) | 0.1304 (3) | 0.1266 (3) | 0.0558 (9) | |
C12 | 0.1473 (5) | 0.1020 (4) | 0.0708 (4) | 0.0775 (13) | |
H12A | 0.1345 | 0.0310 | 0.0349 | 0.093* | |
C13 | 0.0417 (6) | 0.1792 (5) | 0.0691 (5) | 0.0886 (15) | |
H13A | −0.0438 | 0.1605 | 0.0325 | 0.106* | |
C14 | 0.0606 (5) | 0.2840 (4) | 0.1211 (4) | 0.0719 (11) | |
H14A | −0.0106 | 0.3373 | 0.1190 | 0.086* | |
C15 | 0.1869 (4) | 0.3094 (3) | 0.1767 (3) | 0.0549 (8) | |
H15A | 0.1990 | 0.3798 | 0.2139 | 0.066* | |
C16 | 0.3662 (4) | 0.1163 (4) | 0.4101 (3) | 0.0652 (10) | |
H16A | 0.3955 | 0.0529 | 0.3692 | 0.078* | |
C17 | 0.2985 (5) | 0.1049 (5) | 0.5041 (4) | 0.0806 (14) | |
H17A | 0.2844 | 0.0338 | 0.5262 | 0.097* | |
C18 | 0.2533 (5) | 0.1969 (5) | 0.5631 (3) | 0.0823 (14) | |
H18A | 0.2067 | 0.1890 | 0.6249 | 0.099* | |
C19 | 0.2761 (4) | 0.3008 (4) | 0.5316 (3) | 0.0672 (11) | |
H19A | 0.2458 | 0.3645 | 0.5717 | 0.081* | |
C20 | 0.3443 (4) | 0.3107 (3) | 0.4402 (2) | 0.0523 (8) | |
C21 | 0.3797 (4) | 0.4214 (3) | 0.4006 (3) | 0.0527 (8) | |
C22 | 0.5049 (4) | 0.4906 (3) | 0.2525 (3) | 0.0466 (7) | |
C23 | 0.4968 (5) | 0.6065 (3) | 0.2745 (3) | 0.0617 (10) | |
H23A | 0.4490 | 0.6370 | 0.3327 | 0.074* | |
C24 | 0.5625 (5) | 0.6769 (3) | 0.2070 (4) | 0.0744 (12) | |
H24A | 0.5569 | 0.7544 | 0.2219 | 0.089* | |
C25 | 0.6329 (5) | 0.6370 (3) | 0.1220 (4) | 0.0709 (12) | |
H25A | 0.6763 | 0.6868 | 0.0804 | 0.085* | |
C26 | 0.6412 (4) | 0.5202 (3) | 0.0953 (3) | 0.0583 (9) | |
C27 | 0.7120 (4) | 0.4666 (4) | 0.0094 (3) | 0.0629 (10) | |
H27A | 0.7621 | 0.5101 | −0.0346 | 0.075* | |
C28 | 0.7083 (4) | 0.3521 (4) | −0.0105 (3) | 0.0625 (10) | |
H28A | 0.7535 | 0.3176 | −0.0683 | 0.075* | |
C29 | 0.6363 (4) | 0.2882 (3) | 0.0567 (3) | 0.0528 (8) | |
H29A | 0.6335 | 0.2103 | 0.0423 | 0.063* | |
C30 | 0.5729 (4) | 0.4481 (3) | 0.1621 (3) | 0.0467 (7) | |
Cl1 | 0.98024 (13) | 0.38673 (11) | 0.75442 (12) | 0.0874 (4) | |
Fe1 | 0.48026 (5) | 0.25820 (4) | 0.25203 (3) | 0.03984 (17) | |
N1 | 0.6730 (3) | 0.2379 (2) | 0.3095 (2) | 0.0500 (7) | |
N2 | 0.5060 (3) | 0.1068 (2) | 0.1892 (2) | 0.0493 (7) | |
N3 | 0.2932 (3) | 0.2345 (2) | 0.1783 (2) | 0.0439 (6) | |
N4 | 0.3889 (3) | 0.2191 (2) | 0.3789 (2) | 0.0478 (6) | |
N5 | 0.4503 (3) | 0.4062 (2) | 0.3099 (2) | 0.0448 (6) | |
N6 | 0.5710 (3) | 0.3329 (2) | 0.1409 (2) | 0.0437 (6) | |
O1 | 0.3877 (4) | −0.0438 (2) | 0.0916 (3) | 0.0865 (10) | |
O2 | 0.3503 (4) | 0.5108 (3) | 0.4477 (2) | 0.0778 (8) | |
O3 | 1.0848 (7) | 0.4603 (6) | 0.7251 (5) | 0.166 (2) | |
O4 | 0.9827 (10) | 0.2839 (6) | 0.6934 (8) | 0.227 (4) | |
O5 | 1.0194 (7) | 0.3498 (9) | 0.8547 (6) | 0.217 (4) | |
O6 | 0.8419 (5) | 0.4240 (4) | 0.7667 (4) | 0.1305 (16) | |
O1W | 0.2728 (13) | 0.8676 (9) | 0.3076 (14) | 0.131 (3) | |
H1W | 0.205 (4) | 0.839 (4) | 0.339 (3) | 0.080* | |
H2W | 0.265 (5) | 0.846 (5) | 0.2461 (12) | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.065 (2) | 0.067 (2) | 0.062 (2) | 0.0114 (19) | −0.0079 (19) | −0.0116 (19) |
C2 | 0.071 (3) | 0.103 (4) | 0.089 (4) | 0.007 (3) | −0.023 (2) | −0.015 (3) |
C3 | 0.065 (3) | 0.101 (4) | 0.081 (3) | 0.016 (3) | −0.013 (2) | 0.010 (3) |
C4 | 0.068 (2) | 0.073 (3) | 0.061 (2) | 0.024 (2) | 0.0157 (19) | 0.029 (2) |
C5 | 0.072 (3) | 0.082 (3) | 0.089 (3) | 0.028 (2) | 0.013 (2) | 0.026 (3) |
C6 | 0.098 (4) | 0.065 (3) | 0.081 (3) | 0.030 (3) | 0.033 (3) | 0.023 (2) |
C7 | 0.080 (3) | 0.0421 (18) | 0.068 (2) | 0.0120 (17) | 0.019 (2) | 0.0127 (17) |
C8 | 0.065 (2) | 0.0432 (17) | 0.0430 (18) | 0.0080 (15) | 0.0105 (15) | 0.0080 (14) |
C9 | 0.059 (2) | 0.0482 (18) | 0.0431 (18) | 0.0130 (15) | 0.0152 (14) | 0.0123 (14) |
C10 | 0.069 (2) | 0.0368 (17) | 0.061 (2) | −0.0049 (16) | 0.0072 (18) | −0.0056 (15) |
C11 | 0.063 (2) | 0.0456 (18) | 0.057 (2) | −0.0090 (16) | 0.0050 (16) | −0.0014 (15) |
C12 | 0.074 (3) | 0.067 (3) | 0.086 (3) | −0.015 (2) | −0.007 (2) | −0.016 (2) |
C13 | 0.069 (3) | 0.087 (3) | 0.106 (4) | −0.001 (3) | −0.019 (3) | −0.005 (3) |
C14 | 0.058 (2) | 0.080 (3) | 0.078 (3) | 0.005 (2) | −0.007 (2) | 0.010 (2) |
C15 | 0.060 (2) | 0.053 (2) | 0.053 (2) | 0.0063 (16) | 0.0018 (16) | 0.0094 (16) |
C16 | 0.063 (2) | 0.078 (3) | 0.058 (2) | 0.003 (2) | 0.0010 (18) | 0.023 (2) |
C17 | 0.082 (3) | 0.101 (4) | 0.064 (3) | −0.007 (3) | 0.007 (2) | 0.035 (3) |
C18 | 0.075 (3) | 0.128 (5) | 0.045 (2) | −0.004 (3) | 0.014 (2) | 0.016 (3) |
C19 | 0.064 (2) | 0.096 (3) | 0.041 (2) | 0.005 (2) | 0.0107 (16) | 0.001 (2) |
C20 | 0.0500 (19) | 0.072 (2) | 0.0333 (16) | 0.0063 (16) | −0.0027 (13) | −0.0014 (15) |
C21 | 0.055 (2) | 0.057 (2) | 0.0434 (18) | 0.0195 (16) | −0.0027 (15) | −0.0150 (15) |
C22 | 0.0518 (19) | 0.0366 (16) | 0.0495 (19) | 0.0031 (13) | −0.0073 (14) | −0.0048 (13) |
C23 | 0.070 (2) | 0.0432 (18) | 0.069 (3) | 0.0068 (17) | −0.0058 (19) | −0.0076 (17) |
C24 | 0.086 (3) | 0.0384 (19) | 0.099 (4) | −0.0039 (19) | −0.010 (3) | 0.010 (2) |
C25 | 0.075 (3) | 0.051 (2) | 0.088 (3) | −0.015 (2) | −0.008 (2) | 0.021 (2) |
C26 | 0.054 (2) | 0.053 (2) | 0.069 (2) | −0.0122 (17) | −0.0141 (17) | 0.0205 (18) |
C27 | 0.056 (2) | 0.079 (3) | 0.057 (2) | −0.0057 (19) | 0.0038 (17) | 0.027 (2) |
C28 | 0.058 (2) | 0.081 (3) | 0.050 (2) | 0.0023 (19) | 0.0108 (16) | 0.0108 (19) |
C29 | 0.055 (2) | 0.054 (2) | 0.0493 (19) | 0.0042 (15) | 0.0015 (15) | 0.0044 (16) |
C30 | 0.0432 (17) | 0.0452 (17) | 0.0511 (19) | −0.0048 (14) | −0.0085 (14) | 0.0033 (14) |
Cl1 | 0.0700 (7) | 0.0850 (8) | 0.1068 (10) | 0.0213 (6) | 0.0178 (6) | 0.0009 (7) |
Fe1 | 0.0500 (3) | 0.0338 (2) | 0.0350 (3) | 0.00393 (17) | 0.00660 (17) | −0.00136 (17) |
N1 | 0.0540 (16) | 0.0532 (16) | 0.0425 (15) | −0.0015 (13) | 0.0048 (12) | 0.0040 (12) |
N2 | 0.0642 (18) | 0.0317 (13) | 0.0509 (16) | 0.0042 (12) | 0.0100 (13) | −0.0018 (11) |
N3 | 0.0504 (15) | 0.0390 (13) | 0.0419 (14) | −0.0029 (11) | 0.0076 (11) | 0.0028 (11) |
N4 | 0.0561 (16) | 0.0530 (16) | 0.0354 (14) | 0.0044 (13) | 0.0022 (11) | 0.0096 (12) |
N5 | 0.0513 (16) | 0.0417 (14) | 0.0408 (14) | 0.0076 (12) | 0.0022 (11) | −0.0013 (11) |
N6 | 0.0530 (15) | 0.0378 (13) | 0.0392 (14) | −0.0006 (11) | 0.0033 (11) | −0.0011 (11) |
O1 | 0.100 (2) | 0.0401 (14) | 0.113 (3) | −0.0018 (15) | −0.0040 (19) | −0.0202 (15) |
O2 | 0.099 (2) | 0.0683 (18) | 0.0624 (17) | 0.0251 (15) | 0.0108 (15) | −0.0191 (14) |
O3 | 0.149 (5) | 0.175 (6) | 0.180 (6) | −0.043 (4) | 0.034 (4) | 0.052 (5) |
O4 | 0.264 (9) | 0.114 (5) | 0.294 (10) | 0.041 (5) | 0.111 (7) | −0.046 (5) |
O5 | 0.143 (5) | 0.369 (12) | 0.157 (6) | 0.035 (6) | 0.007 (4) | 0.110 (7) |
O6 | 0.107 (3) | 0.134 (4) | 0.157 (4) | 0.057 (3) | 0.024 (3) | 0.027 (3) |
O1W | 0.188 (9) | 0.117 (6) | 0.088 (6) | 0.054 (6) | 0.041 (5) | −0.008 (5) |
C1—N1 | 1.327 (5) | C18—H18A | 0.930 |
C1—C2 | 1.410 (6) | C19—C20 | 1.368 (5) |
C1—H1A | 0.930 | C19—H19A | 0.930 |
C2—C3 | 1.332 (7) | C20—N4 | 1.363 (5) |
C2—H2A | 0.930 | C20—C21 | 1.496 (6) |
C3—C4 | 1.422 (7) | C21—O2 | 1.215 (4) |
C3—H3A | 0.930 | C21—N5 | 1.356 (4) |
C4—C5 | 1.407 (7) | C22—C23 | 1.389 (5) |
C4—C9 | 1.406 (6) | C22—C30 | 1.398 (5) |
C5—C6 | 1.336 (8) | C22—N5 | 1.400 (4) |
C5—H5A | 0.930 | C23—C24 | 1.408 (6) |
C6—C7 | 1.416 (7) | C23—H23A | 0.930 |
C6—H6A | 0.930 | C24—C25 | 1.343 (7) |
C7—C8 | 1.365 (5) | C24—H24A | 0.930 |
C7—H7A | 0.930 | C25—C26 | 1.408 (6) |
C8—N2 | 1.392 (5) | C25—H25A | 0.930 |
C8—C9 | 1.445 (5) | C26—C27 | 1.409 (6) |
C9—N1 | 1.368 (5) | C26—C30 | 1.424 (5) |
C10—O1 | 1.239 (4) | C27—C28 | 1.366 (6) |
C10—N2 | 1.352 (5) | C27—H27A | 0.930 |
C10—C11 | 1.470 (6) | C28—C29 | 1.381 (5) |
C11—N3 | 1.359 (4) | C28—H28A | 0.930 |
C11—C12 | 1.396 (6) | C29—N6 | 1.330 (5) |
C12—C13 | 1.363 (7) | C29—H29A | 0.930 |
C12—H12A | 0.930 | C30—N6 | 1.376 (4) |
C13—C14 | 1.368 (7) | Cl1—O3 | 1.371 (5) |
C13—H13A | 0.930 | Cl1—O6 | 1.372 (4) |
C14—C15 | 1.380 (6) | Cl1—O4 | 1.395 (7) |
C14—H14A | 0.930 | Cl1—O5 | 1.469 (7) |
C15—N3 | 1.349 (5) | Fe1—N5 | 1.880 (3) |
C15—H15A | 0.930 | Fe1—N2 | 1.930 (3) |
C16—N4 | 1.343 (5) | Fe1—N1 | 1.959 (3) |
C16—C17 | 1.400 (6) | Fe1—N4 | 1.958 (3) |
C16—H16A | 0.930 | Fe1—N6 | 1.960 (3) |
C17—C18 | 1.355 (8) | Fe1—N3 | 1.972 (3) |
C17—H17A | 0.930 | O1W—H1W | 0.84 (3) |
C18—C19 | 1.357 (7) | O1W—H2W | 0.82 (3) |
N1—C1—C2 | 120.6 (4) | C30—C22—N5 | 113.1 (3) |
N1—C1—H1A | 119.7 | C22—C23—C24 | 118.8 (4) |
C2—C1—H1A | 119.7 | C22—C23—H23A | 120.6 |
C3—C2—C1 | 120.5 (5) | C24—C23—H23A | 120.6 |
C3—C2—H2A | 119.7 | C25—C24—C23 | 122.9 (4) |
C1—C2—H2A | 119.7 | C25—C24—H24A | 118.6 |
C2—C3—C4 | 121.0 (4) | C23—C24—H24A | 118.6 |
C2—C3—H3A | 119.5 | C24—C25—C26 | 120.4 (4) |
C4—C3—H3A | 119.5 | C24—C25—H25A | 119.8 |
C5—C4—C9 | 117.4 (4) | C26—C25—H25A | 119.8 |
C5—C4—C3 | 126.9 (4) | C27—C26—C25 | 126.5 (4) |
C9—C4—C3 | 115.7 (4) | C27—C26—C30 | 116.3 (3) |
C6—C5—C4 | 121.5 (5) | C25—C26—C30 | 117.2 (4) |
C6—C5—H5A | 119.3 | C28—C27—C26 | 121.2 (4) |
C4—C5—H5A | 119.3 | C28—C27—H27A | 119.4 |
C5—C6—C7 | 122.1 (4) | C26—C27—H27A | 119.4 |
C5—C6—H6A | 119.0 | C27—C28—C29 | 118.9 (4) |
C7—C6—H6A | 119.0 | C27—C28—H28A | 120.5 |
C8—C7—C6 | 119.4 (4) | C29—C28—H28A | 120.5 |
C8—C7—H7A | 120.3 | N6—C29—C28 | 123.1 (4) |
C6—C7—H7A | 120.3 | N6—C29—H29A | 118.5 |
C7—C8—N2 | 129.4 (4) | C28—C29—H29A | 118.5 |
C7—C8—C9 | 118.7 (4) | N6—C30—C22 | 116.6 (3) |
N2—C8—C9 | 111.8 (3) | N6—C30—C26 | 121.5 (3) |
N1—C9—C4 | 122.6 (4) | C22—C30—C26 | 121.9 (3) |
N1—C9—C8 | 116.5 (3) | O3—Cl1—O6 | 118.2 (4) |
C4—C9—C8 | 120.9 (3) | O3—Cl1—O4 | 111.2 (5) |
O1—C10—N2 | 128.8 (4) | O6—Cl1—O4 | 111.5 (5) |
O1—C10—C11 | 120.9 (4) | O3—Cl1—O5 | 109.7 (5) |
N2—C10—C11 | 110.3 (3) | O6—Cl1—O5 | 104.6 (4) |
N3—C11—C12 | 120.0 (4) | O4—Cl1—O5 | 99.8 (6) |
N3—C11—C10 | 116.0 (3) | N5—Fe1—N2 | 178.08 (13) |
C12—C11—C10 | 124.1 (3) | N5—Fe1—N1 | 98.93 (12) |
C13—C12—C11 | 119.5 (4) | N2—Fe1—N1 | 82.88 (12) |
C13—C12—H12A | 120.3 | N5—Fe1—N4 | 83.05 (12) |
C11—C12—H12A | 120.3 | N2—Fe1—N4 | 97.59 (12) |
C12—C13—C14 | 120.4 (4) | N1—Fe1—N4 | 91.11 (12) |
C12—C13—H13A | 119.8 | N5—Fe1—N6 | 83.80 (11) |
C14—C13—H13A | 119.8 | N2—Fe1—N6 | 95.61 (11) |
C13—C14—C15 | 118.9 (4) | N1—Fe1—N6 | 89.06 (12) |
C13—C14—H14A | 120.5 | N4—Fe1—N6 | 166.71 (11) |
C15—C14—H14A | 120.5 | N5—Fe1—N3 | 97.17 (12) |
N3—C15—C14 | 121.4 (4) | N2—Fe1—N3 | 81.03 (12) |
N3—C15—H15A | 119.3 | N1—Fe1—N3 | 163.89 (12) |
C14—C15—H15A | 119.3 | N4—Fe1—N3 | 90.17 (11) |
N4—C16—C17 | 119.9 (4) | N6—Fe1—N3 | 93.34 (11) |
N4—C16—H16A | 120.0 | C1—N1—C9 | 119.6 (3) |
C17—C16—H16A | 120.0 | C1—N1—Fe1 | 127.3 (3) |
C18—C17—C16 | 120.2 (5) | C9—N1—Fe1 | 113.1 (2) |
C18—C17—H17A | 119.9 | C10—N2—C8 | 125.6 (3) |
C16—C17—H17A | 119.9 | C10—N2—Fe1 | 118.8 (2) |
C19—C18—C17 | 119.8 (4) | C8—N2—Fe1 | 115.6 (2) |
C19—C18—H18A | 120.1 | C15—N3—C11 | 119.7 (3) |
C17—C18—H18A | 120.1 | C15—N3—Fe1 | 126.5 (2) |
C18—C19—C20 | 119.2 (4) | C11—N3—Fe1 | 113.8 (2) |
C18—C19—H19A | 120.4 | C16—N4—C20 | 118.8 (3) |
C20—C19—H19A | 120.4 | C16—N4—Fe1 | 128.1 (3) |
N4—C20—C19 | 122.0 (4) | C20—N4—Fe1 | 113.1 (2) |
N4—C20—C21 | 114.7 (3) | C21—N5—C22 | 126.6 (3) |
C19—C20—C21 | 123.4 (4) | C21—N5—Fe1 | 118.4 (2) |
O2—C21—N5 | 126.8 (4) | C22—N5—Fe1 | 115.0 (2) |
O2—C21—C20 | 122.5 (3) | C29—N6—C30 | 118.9 (3) |
N5—C21—C20 | 110.7 (3) | C29—N6—Fe1 | 129.5 (2) |
C23—C22—C30 | 118.8 (3) | C30—N6—Fe1 | 111.4 (2) |
C23—C22—N5 | 128.1 (3) | H1W—O1W—H2W | 109 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O4i | 0.84 (3) | 2.25 (4) | 2.934 (12) | 139 (4) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Fe(C15H10N3O)2]ClO4·H2O |
Mr | 669.84 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.2452 (10), 11.944 (2), 13.0523 (10) |
α, β, γ (°) | 95.807 (5), 90.462 (1), 91.615 (5) |
V (Å3) | 1433.3 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.68 |
Crystal size (mm) | 0.42 × 0.26 × 0.22 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.763, 0.865 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13425, 5559, 3729 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.140, 1.00 |
No. of reflections | 5559 |
No. of parameters | 413 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.50, −0.42 |
Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O4i | 0.84 (3) | 2.25 (4) | 2.934 (12) | 139 (4) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Complexes containing carbonyl amine (organic amide) ligands have been the interest of chemists due to their potential applications, such as in catalysis, optics, information storage, medicine, molecular electrochemistry, biochemistry and biological pharmaceuticals (Li et al., 1993; Go et al., 2004). Thus far, N-containing aromatic carbonyl amines have been widely used in dye intermediates, organic synthesis, sensitization materials, functional pigments, adipiodone and acetrizoic acid (An et al., 2000). Pyridine carbonyl amine is also a good ligand in coordination chemistry due to its strong coordination ability and versatile coordination modes, so much attention has been paid to it in recent years (Baroni et al., 1996; Hundal et al., 2002). Here we report the new title complex.
The title compound contains an iron(III) cation chelated by two 2-pyridinecarbonyl-8-aminoquinoline ligands via six N atoms, exhibiting octahedral geometry around the central iron ion (Fig. 1). The Fe—N bond length are in the range 1.880 (3)–1.972 (3) Å. Each ligand is planar (r.m.s. deviations 0.0314 and 0.0282 Å). The dihedral angle between the two ligand planes is 86.55 (1)°. There is a weak intermolecular hydrogen bond between water and perchlorate, contributing to the packing.