In the title compound, [FeCl(C
18H
14N
2O
6)], the iron(III) is coordinated by N and O atoms at the basal sites and Cl at the apical site to form a distorted square pyramid. Hydrogen bonding in carboxylic acid dimers and π–π stacking interactions through benzene rings of the ligand lead to paired chains, which are alternately crosslinked with each other to form a non-porous solid. The title compound is potentially a good building block for the construction of highly porous mixed-metal-organic frameworks (M'MOFs). The O
O distances in the carboxylic acid dimers are 2.555 (6) and 2.664 (6) Å.
Supporting information
CCDC reference: 242026
Key indicators
- Single-crystal X-ray study
- T = 102 K
- Mean (C-C) = 0.010 Å
- R factor = 0.074
- wR factor = 0.167
- Data-to-parameter ratio = 13.9
checkCIF/PLATON results
No syntax errors found
Alert level A
RINTA01_ALERT_3_A The value of Rint is greater than 0.20
Rint given 0.214
| Author Response: This is a result of the extremely small size
of the best crystals we could grow. The data were collected
very slowly at low T. The fact that we were able to solve
the structure, refine non-H atoms to fairly reasonably
shaped ellipsoids, and see the H atoms in difference maps
is a testament to the power of modern instrumentation. We
comment in the _publ_section_exptl_refinement on the limitations caused
by the small sample size. The limited precision of the
results resulted in submission to Acta E rather than Section C.
|
PLAT020_ALERT_3_A The value of Rint is greater than 0.10 ......... 0.21
| Author Response: See above.
|
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc.
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.03
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
2 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Chloro[
N,
N'-ethylenebis(5-carboxysalicylideneiminato)]iron(III)
top
Crystal data top
[FeCl(C18H14N2O6)] | F(000) = 908 |
Mr = 445.61 | Dx = 1.633 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6177 reflections |
a = 9.177 (5) Å | θ = 2.5–26.0° |
b = 15.124 (10) Å | µ = 1.02 mm−1 |
c = 13.334 (7) Å | T = 102 K |
β = 101.73 (2)° | Blade, red |
V = 1812.0 (18) Å3 | 0.13 × 0.05 × 0.01 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler) diffractometer | 3554 independent reflections |
Radiation source: fine-focus sealed tube | 1615 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.214 |
ω scans with κ offsets | θmax = 26.2°, θmin = 3.1° |
Absorption correction: multi-scan (HKL SCALEPACK; Otwinowski & Minor, 1997) | h = −10→11 |
Tmin = 0.933, Tmax = 0.990 | k = −18→18 |
19196 measured reflections | l = −16→16 |
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)] = 0.074 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0487P)2 + 0.9967P] where P = (Fo2 + 2Fc2)/3 |
3554 reflections | (Δ/σ)max < 0.001 |
255 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Fe1 | 0.59099 (11) | 0.51971 (6) | 0.36826 (9) | 0.0293 (3) | |
Cl1 | 0.6587 (2) | 0.60412 (14) | 0.24890 (17) | 0.0482 (6) | |
O1 | 0.7640 (5) | 0.4637 (3) | 0.4402 (4) | 0.0281 (12) | |
O2 | 0.5784 (5) | 0.6022 (3) | 0.4744 (4) | 0.0321 (12) | |
O3 | 1.1629 (5) | 0.1255 (3) | 0.4965 (4) | 0.0372 (14) | |
H3O | 1.2033 | 0.0773 | 0.4867 | 0.056* | |
O4 | 0.9777 (5) | 0.0708 (3) | 0.3781 (4) | 0.0329 (13) | |
O5 | 0.1144 (5) | 0.9162 (3) | 0.3708 (4) | 0.0340 (13) | |
H5O | 0.0777 | 0.9672 | 0.3691 | 0.051* | |
O6 | 0.2972 (5) | 0.9789 (3) | 0.4856 (4) | 0.0347 (12) | |
N1 | 0.5306 (6) | 0.3983 (4) | 0.2977 (4) | 0.0272 (14) | |
N2 | 0.3560 (6) | 0.5279 (4) | 0.3316 (4) | 0.0281 (14) | |
C1 | 0.8275 (7) | 0.3866 (4) | 0.4336 (6) | 0.0257 (17) | |
C2 | 0.9716 (7) | 0.3716 (4) | 0.4914 (6) | 0.0289 (18) | |
H2 | 1.0226 | 0.4182 | 0.5317 | 0.035* | |
C3 | 1.0394 (7) | 0.2916 (5) | 0.4907 (6) | 0.0308 (19) | |
H3 | 1.1375 | 0.2834 | 0.5294 | 0.037* | |
C4 | 0.9651 (8) | 0.2203 (4) | 0.4328 (6) | 0.0282 (18) | |
C5 | 0.8241 (7) | 0.2342 (4) | 0.3761 (5) | 0.0234 (16) | |
H5 | 0.7733 | 0.1866 | 0.3376 | 0.028* | |
C6 | 0.7532 (7) | 0.3163 (4) | 0.3736 (5) | 0.0221 (16) | |
C7 | 0.6047 (8) | 0.3247 (5) | 0.3109 (5) | 0.0273 (17) | |
H7 | 0.5591 | 0.2733 | 0.2776 | 0.033* | |
C8 | 0.3841 (8) | 0.3981 (5) | 0.2319 (6) | 0.0367 (19) | |
H8A | 0.3488 | 0.3366 | 0.2180 | 0.044* | |
H8B | 0.3877 | 0.4269 | 0.1658 | 0.044* | |
C9 | 0.2787 (8) | 0.4484 (4) | 0.2862 (6) | 0.0319 (18) | |
H9A | 0.1869 | 0.4648 | 0.2367 | 0.038* | |
H9B | 0.2507 | 0.4110 | 0.3402 | 0.038* | |
C10 | 0.2833 (8) | 0.5978 (4) | 0.3453 (5) | 0.0260 (17) | |
H10 | 0.1787 | 0.5982 | 0.3206 | 0.031* | |
C11 | 0.3523 (7) | 0.6760 (4) | 0.3963 (5) | 0.0224 (16) | |
C12 | 0.2685 (8) | 0.7550 (4) | 0.3877 (6) | 0.0258 (17) | |
H12 | 0.1702 | 0.7558 | 0.3477 | 0.031* | |
C13 | 0.3291 (7) | 0.8321 (4) | 0.4376 (5) | 0.0226 (16) | |
C14 | 0.4725 (7) | 0.8293 (5) | 0.4997 (6) | 0.0279 (18) | |
H14 | 0.5144 | 0.8815 | 0.5335 | 0.034* | |
C15 | 0.5523 (7) | 0.7524 (4) | 0.5120 (5) | 0.0239 (17) | |
H15 | 0.6471 | 0.7512 | 0.5568 | 0.029* | |
C16 | 0.4975 (7) | 0.6759 (4) | 0.4601 (6) | 0.0289 (18) | |
C17 | 1.0357 (8) | 0.1323 (4) | 0.4327 (6) | 0.0305 (19) | |
C18 | 0.2460 (7) | 0.9158 (4) | 0.4327 (5) | 0.0250 (17) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.0317 (6) | 0.0227 (5) | 0.0303 (6) | 0.0076 (5) | −0.0013 (4) | −0.0019 (6) |
Cl1 | 0.0601 (14) | 0.0407 (13) | 0.0438 (14) | 0.0025 (10) | 0.0111 (11) | 0.0080 (11) |
O1 | 0.026 (3) | 0.015 (2) | 0.042 (3) | 0.008 (2) | 0.003 (2) | −0.002 (2) |
O2 | 0.037 (3) | 0.020 (3) | 0.034 (3) | 0.011 (2) | −0.003 (2) | −0.004 (2) |
O3 | 0.026 (3) | 0.024 (3) | 0.055 (4) | 0.008 (2) | −0.007 (3) | −0.009 (3) |
O4 | 0.029 (3) | 0.019 (3) | 0.047 (4) | 0.007 (2) | 0.000 (3) | −0.009 (3) |
O5 | 0.029 (3) | 0.022 (3) | 0.045 (3) | 0.010 (2) | −0.006 (3) | −0.004 (3) |
O6 | 0.034 (3) | 0.017 (2) | 0.049 (3) | 0.004 (2) | 0.000 (2) | −0.009 (3) |
N1 | 0.026 (3) | 0.032 (3) | 0.018 (3) | 0.006 (3) | −0.009 (3) | −0.003 (3) |
N2 | 0.038 (3) | 0.019 (3) | 0.026 (3) | 0.008 (3) | 0.002 (3) | −0.005 (3) |
C1 | 0.028 (4) | 0.018 (4) | 0.031 (5) | 0.007 (3) | 0.006 (4) | 0.003 (3) |
C2 | 0.025 (4) | 0.017 (4) | 0.041 (5) | 0.007 (3) | −0.001 (4) | −0.002 (3) |
C3 | 0.020 (4) | 0.033 (4) | 0.039 (5) | −0.003 (3) | 0.005 (4) | −0.003 (4) |
C4 | 0.026 (4) | 0.023 (4) | 0.037 (5) | 0.002 (3) | 0.010 (4) | 0.000 (4) |
C5 | 0.024 (4) | 0.018 (4) | 0.027 (4) | 0.004 (3) | 0.004 (3) | −0.003 (3) |
C6 | 0.024 (4) | 0.021 (4) | 0.020 (4) | 0.005 (3) | 0.003 (3) | 0.003 (3) |
C7 | 0.038 (4) | 0.025 (4) | 0.019 (4) | 0.003 (3) | 0.007 (3) | 0.001 (3) |
C8 | 0.035 (4) | 0.033 (4) | 0.037 (5) | 0.009 (4) | −0.004 (4) | −0.006 (4) |
C9 | 0.034 (4) | 0.021 (4) | 0.035 (5) | 0.006 (3) | −0.006 (4) | −0.003 (3) |
C10 | 0.034 (4) | 0.025 (4) | 0.019 (4) | 0.007 (3) | 0.004 (3) | 0.007 (3) |
C11 | 0.027 (4) | 0.013 (3) | 0.027 (4) | 0.007 (3) | 0.007 (3) | −0.004 (3) |
C12 | 0.029 (4) | 0.024 (4) | 0.029 (4) | 0.006 (3) | 0.018 (4) | 0.000 (3) |
C13 | 0.023 (4) | 0.018 (4) | 0.030 (5) | 0.005 (3) | 0.012 (3) | 0.002 (3) |
C14 | 0.031 (4) | 0.015 (4) | 0.038 (5) | −0.006 (3) | 0.008 (4) | 0.002 (3) |
C15 | 0.018 (4) | 0.019 (4) | 0.032 (5) | 0.004 (3) | 0.001 (3) | 0.003 (3) |
C16 | 0.024 (4) | 0.024 (4) | 0.037 (5) | 0.012 (3) | 0.004 (4) | 0.001 (4) |
C17 | 0.023 (4) | 0.020 (4) | 0.047 (5) | 0.001 (3) | 0.005 (4) | −0.002 (4) |
C18 | 0.029 (4) | 0.018 (4) | 0.029 (5) | 0.006 (3) | 0.008 (4) | 0.000 (3) |
Geometric parameters (Å, º) top
Fe1—O1 | 1.881 (4) | C4—C5 | 1.375 (9) |
Fe1—O2 | 1.907 (5) | C4—C17 | 1.481 (9) |
Fe1—N1 | 2.086 (6) | C5—C6 | 1.398 (8) |
Fe1—N2 | 2.116 (6) | C5—H5 | 0.9500 |
Fe1—Cl1 | 2.225 (3) | C6—C7 | 1.453 (9) |
O1—C1 | 1.315 (7) | C7—H7 | 0.9500 |
O2—C16 | 1.332 (7) | C8—C9 | 1.524 (9) |
O3—C17 | 1.301 (8) | C8—H8A | 0.9900 |
O3—H3O | 0.8400 | C8—H8B | 0.9900 |
O4—C17 | 1.233 (8) | C9—H9A | 0.9900 |
O5—C18 | 1.317 (8) | C9—H9B | 0.9900 |
O5—H5O | 0.8400 | C10—C11 | 1.445 (9) |
O6—C18 | 1.223 (8) | C10—H10 | 0.9500 |
N1—C7 | 1.298 (8) | C11—C12 | 1.413 (8) |
N1—C8 | 1.449 (9) | C11—C16 | 1.427 (9) |
N2—C10 | 1.282 (8) | C12—C13 | 1.401 (9) |
N2—C9 | 1.463 (8) | C12—H12 | 0.9500 |
C1—C2 | 1.408 (9) | C13—C14 | 1.405 (9) |
C1—C6 | 1.419 (9) | C13—C18 | 1.472 (9) |
C2—C3 | 1.362 (9) | C14—C15 | 1.367 (9) |
C2—H2 | 0.9500 | C14—H14 | 0.9500 |
C3—C4 | 1.417 (9) | C15—C16 | 1.389 (9) |
C3—H3 | 0.9500 | C15—H15 | 0.9500 |
| | | |
O1—Fe1—O2 | 95.1 (2) | C6—C7—H7 | 118.0 |
O1—Fe1—N1 | 87.3 (2) | N1—C8—C9 | 108.2 (6) |
O2—Fe1—N1 | 149.3 (2) | N1—C8—H8A | 110.1 |
O1—Fe1—N2 | 149.2 (2) | C9—C8—H8A | 110.1 |
O2—Fe1—N2 | 85.4 (2) | N1—C8—H8B | 110.1 |
N1—Fe1—N2 | 77.4 (2) | C9—C8—H8B | 110.1 |
O1—Fe1—Cl1 | 107.07 (16) | H8A—C8—H8B | 108.4 |
O2—Fe1—Cl1 | 102.90 (16) | N2—C9—C8 | 107.8 (6) |
N1—Fe1—Cl1 | 105.63 (18) | N2—C9—H9A | 110.1 |
N2—Fe1—Cl1 | 102.78 (17) | C8—C9—H9A | 110.1 |
C1—O1—Fe1 | 134.8 (4) | N2—C9—H9B | 110.1 |
C16—O2—Fe1 | 123.9 (5) | C8—C9—H9B | 110.1 |
C17—O3—H3O | 109.5 | H9A—C9—H9B | 108.5 |
C18—O5—H5O | 109.5 | N2—C10—C11 | 123.5 (6) |
C7—N1—C8 | 118.5 (6) | N2—C10—H10 | 118.3 |
C7—N1—Fe1 | 127.6 (5) | C11—C10—H10 | 118.3 |
C8—N1—Fe1 | 113.8 (4) | C12—C11—C16 | 118.5 (6) |
C10—N2—C9 | 120.9 (6) | C12—C11—C10 | 118.3 (6) |
C10—N2—Fe1 | 123.4 (5) | C16—C11—C10 | 123.1 (6) |
C9—N2—Fe1 | 115.7 (4) | C13—C12—C11 | 120.5 (7) |
O1—C1—C2 | 119.1 (6) | C13—C12—H12 | 119.7 |
O1—C1—C6 | 122.3 (6) | C11—C12—H12 | 119.7 |
C2—C1—C6 | 118.6 (6) | C12—C13—C14 | 119.2 (6) |
C3—C2—C1 | 121.2 (7) | C12—C13—C18 | 122.8 (6) |
C3—C2—H2 | 119.4 | C14—C13—C18 | 117.9 (6) |
C1—C2—H2 | 119.4 | C15—C14—C13 | 120.7 (7) |
C2—C3—C4 | 120.6 (6) | C15—C14—H14 | 119.6 |
C2—C3—H3 | 119.7 | C13—C14—H14 | 119.6 |
C4—C3—H3 | 119.7 | C14—C15—C16 | 121.2 (7) |
C5—C4—C3 | 118.5 (6) | C14—C15—H15 | 119.4 |
C5—C4—C17 | 120.0 (6) | C16—C15—H15 | 119.4 |
C3—C4—C17 | 121.4 (6) | O2—C16—C15 | 119.4 (6) |
C4—C5—C6 | 122.0 (6) | O2—C16—C11 | 120.8 (6) |
C4—C5—H5 | 119.0 | C15—C16—C11 | 119.7 (6) |
C6—C5—H5 | 119.0 | O4—C17—O3 | 123.3 (6) |
C5—C6—C1 | 118.9 (6) | O4—C17—C4 | 122.8 (7) |
C5—C6—C7 | 118.0 (6) | O3—C17—C4 | 113.9 (6) |
C1—C6—C7 | 123.1 (6) | O6—C18—O5 | 123.6 (6) |
N1—C7—C6 | 123.9 (6) | O6—C18—C13 | 120.7 (6) |
N1—C7—H7 | 118.0 | O5—C18—C13 | 115.7 (6) |
| | | |
O2—Fe1—O1—C1 | 159.6 (6) | C2—C1—C6—C7 | −179.8 (7) |
N1—Fe1—O1—C1 | 10.3 (6) | C8—N1—C7—C6 | 179.1 (7) |
N2—Fe1—O1—C1 | 70.0 (8) | Fe1—N1—C7—C6 | −5.3 (10) |
Cl1—Fe1—O1—C1 | −95.2 (6) | C5—C6—C7—N1 | −176.1 (7) |
O1—Fe1—O2—C16 | 162.6 (5) | C1—C6—C7—N1 | 5.4 (11) |
N1—Fe1—O2—C16 | −104.2 (6) | C7—N1—C8—C9 | 134.0 (7) |
N2—Fe1—O2—C16 | −48.3 (5) | Fe1—N1—C8—C9 | −42.2 (7) |
Cl1—Fe1—O2—C16 | 53.8 (5) | C10—N2—C9—C8 | 151.9 (6) |
O1—Fe1—N1—C7 | −1.0 (6) | Fe1—N2—C9—C8 | −26.6 (7) |
O2—Fe1—N1—C7 | −96.4 (7) | N1—C8—C9—N2 | 43.2 (8) |
N2—Fe1—N1—C7 | −154.1 (6) | C9—N2—C10—C11 | 175.4 (6) |
Cl1—Fe1—N1—C7 | 106.0 (6) | Fe1—N2—C10—C11 | −6.2 (10) |
O1—Fe1—N1—C8 | 174.9 (5) | N2—C10—C11—C12 | 166.4 (6) |
O2—Fe1—N1—C8 | 79.5 (7) | N2—C10—C11—C16 | −17.5 (11) |
N2—Fe1—N1—C8 | 21.8 (5) | C16—C11—C12—C13 | 2.4 (10) |
Cl1—Fe1—N1—C8 | −78.2 (5) | C10—C11—C12—C13 | 178.6 (6) |
O1—Fe1—N2—C10 | 123.3 (6) | C11—C12—C13—C14 | −2.4 (10) |
O2—Fe1—N2—C10 | 31.1 (6) | C11—C12—C13—C18 | −179.0 (6) |
N1—Fe1—N2—C10 | −174.5 (6) | C12—C13—C14—C15 | −0.3 (10) |
Cl1—Fe1—N2—C10 | −71.1 (6) | C18—C13—C14—C15 | 176.5 (6) |
O1—Fe1—N2—C9 | −58.2 (7) | C13—C14—C15—C16 | 3.0 (11) |
O2—Fe1—N2—C9 | −150.4 (5) | Fe1—O2—C16—C15 | −142.0 (6) |
N1—Fe1—N2—C9 | 3.9 (5) | Fe1—O2—C16—C11 | 41.2 (9) |
Cl1—Fe1—N2—C9 | 107.4 (5) | C14—C15—C16—O2 | −179.8 (7) |
Fe1—O1—C1—C2 | 170.2 (5) | C14—C15—C16—C11 | −3.0 (11) |
Fe1—O1—C1—C6 | −12.7 (11) | C12—C11—C16—O2 | 177.0 (6) |
O1—C1—C2—C3 | 177.0 (7) | C10—C11—C16—O2 | 1.0 (11) |
C6—C1—C2—C3 | −0.2 (11) | C12—C11—C16—C15 | 0.3 (11) |
C1—C2—C3—C4 | −1.1 (11) | C10—C11—C16—C15 | −175.7 (7) |
C2—C3—C4—C5 | 1.0 (11) | C5—C4—C17—O4 | 5.0 (12) |
C2—C3—C4—C17 | −178.8 (7) | C3—C4—C17—O4 | −175.2 (7) |
C3—C4—C5—C6 | 0.5 (11) | C5—C4—C17—O3 | −174.0 (7) |
C17—C4—C5—C6 | −179.7 (7) | C3—C4—C17—O3 | 5.8 (10) |
C4—C5—C6—C1 | −1.8 (11) | C12—C13—C18—O6 | 172.5 (7) |
C4—C5—C6—C7 | 179.6 (7) | C14—C13—C18—O6 | −4.1 (10) |
O1—C1—C6—C5 | −175.5 (6) | C12—C13—C18—O5 | −5.7 (10) |
C2—C1—C6—C5 | 1.7 (10) | C14—C13—C18—O5 | 177.6 (6) |
O1—C1—C6—C7 | 3.1 (11) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3O···O6i | 0.84 | 1.72 | 2.555 (6) | 172 |
O5—H5O···O4ii | 0.84 | 1.83 | 2.664 (6) | 171 |
Symmetry codes: (i) x+1, y−1, z; (ii) x−1, y+1, z. |