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In the title compound, [FeCl(C18H14N2O6)], 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680401030X/lh6213sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680401030X/lh6213Isup2.hkl
Contains datablock I

CCDC reference: 242026

Key indicators

  • Single-crystal X-ray study
  • T = 102 K
  • Mean [sigma](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

Computing details top

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 = 445.61Dx = 1.633 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6177 reflections
a = 9.177 (5) Åθ = 2.5–26.0°
b = 15.124 (10) ŵ = 1.02 mm1
c = 13.334 (7) ÅT = 102 K
β = 101.73 (2)°Blade, red
V = 1812.0 (18) Å30.13 × 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 tube1615 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.214
ω scans with κ offsetsθmax = 26.2°, θmin = 3.1°
Absorption correction: multi-scan
(HKL SCALEPACK; Otwinowski & Minor, 1997)
h = 1011
Tmin = 0.933, Tmax = 0.990k = 1818
19196 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H-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 parametersΔρmax = 0.45 e Å3
0 restraintsΔρmin = 0.44 e Å3
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
xyzUiso*/Ueq
Fe10.59099 (11)0.51971 (6)0.36826 (9)0.0293 (3)
Cl10.6587 (2)0.60412 (14)0.24890 (17)0.0482 (6)
O10.7640 (5)0.4637 (3)0.4402 (4)0.0281 (12)
O20.5784 (5)0.6022 (3)0.4744 (4)0.0321 (12)
O31.1629 (5)0.1255 (3)0.4965 (4)0.0372 (14)
H3O1.20330.07730.48670.056*
O40.9777 (5)0.0708 (3)0.3781 (4)0.0329 (13)
O50.1144 (5)0.9162 (3)0.3708 (4)0.0340 (13)
H5O0.07770.96720.36910.051*
O60.2972 (5)0.9789 (3)0.4856 (4)0.0347 (12)
N10.5306 (6)0.3983 (4)0.2977 (4)0.0272 (14)
N20.3560 (6)0.5279 (4)0.3316 (4)0.0281 (14)
C10.8275 (7)0.3866 (4)0.4336 (6)0.0257 (17)
C20.9716 (7)0.3716 (4)0.4914 (6)0.0289 (18)
H21.02260.41820.53170.035*
C31.0394 (7)0.2916 (5)0.4907 (6)0.0308 (19)
H31.13750.28340.52940.037*
C40.9651 (8)0.2203 (4)0.4328 (6)0.0282 (18)
C50.8241 (7)0.2342 (4)0.3761 (5)0.0234 (16)
H50.77330.18660.33760.028*
C60.7532 (7)0.3163 (4)0.3736 (5)0.0221 (16)
C70.6047 (8)0.3247 (5)0.3109 (5)0.0273 (17)
H70.55910.27330.27760.033*
C80.3841 (8)0.3981 (5)0.2319 (6)0.0367 (19)
H8A0.34880.33660.21800.044*
H8B0.38770.42690.16580.044*
C90.2787 (8)0.4484 (4)0.2862 (6)0.0319 (18)
H9A0.18690.46480.23670.038*
H9B0.25070.41100.34020.038*
C100.2833 (8)0.5978 (4)0.3453 (5)0.0260 (17)
H100.17870.59820.32060.031*
C110.3523 (7)0.6760 (4)0.3963 (5)0.0224 (16)
C120.2685 (8)0.7550 (4)0.3877 (6)0.0258 (17)
H120.17020.75580.34770.031*
C130.3291 (7)0.8321 (4)0.4376 (5)0.0226 (16)
C140.4725 (7)0.8293 (5)0.4997 (6)0.0279 (18)
H140.51440.88150.53350.034*
C150.5523 (7)0.7524 (4)0.5120 (5)0.0239 (17)
H150.64710.75120.55680.029*
C160.4975 (7)0.6759 (4)0.4601 (6)0.0289 (18)
C171.0357 (8)0.1323 (4)0.4327 (6)0.0305 (19)
C180.2460 (7)0.9158 (4)0.4327 (5)0.0250 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0317 (6)0.0227 (5)0.0303 (6)0.0076 (5)0.0013 (4)0.0019 (6)
Cl10.0601 (14)0.0407 (13)0.0438 (14)0.0025 (10)0.0111 (11)0.0080 (11)
O10.026 (3)0.015 (2)0.042 (3)0.008 (2)0.003 (2)0.002 (2)
O20.037 (3)0.020 (3)0.034 (3)0.011 (2)0.003 (2)0.004 (2)
O30.026 (3)0.024 (3)0.055 (4)0.008 (2)0.007 (3)0.009 (3)
O40.029 (3)0.019 (3)0.047 (4)0.007 (2)0.000 (3)0.009 (3)
O50.029 (3)0.022 (3)0.045 (3)0.010 (2)0.006 (3)0.004 (3)
O60.034 (3)0.017 (2)0.049 (3)0.004 (2)0.000 (2)0.009 (3)
N10.026 (3)0.032 (3)0.018 (3)0.006 (3)0.009 (3)0.003 (3)
N20.038 (3)0.019 (3)0.026 (3)0.008 (3)0.002 (3)0.005 (3)
C10.028 (4)0.018 (4)0.031 (5)0.007 (3)0.006 (4)0.003 (3)
C20.025 (4)0.017 (4)0.041 (5)0.007 (3)0.001 (4)0.002 (3)
C30.020 (4)0.033 (4)0.039 (5)0.003 (3)0.005 (4)0.003 (4)
C40.026 (4)0.023 (4)0.037 (5)0.002 (3)0.010 (4)0.000 (4)
C50.024 (4)0.018 (4)0.027 (4)0.004 (3)0.004 (3)0.003 (3)
C60.024 (4)0.021 (4)0.020 (4)0.005 (3)0.003 (3)0.003 (3)
C70.038 (4)0.025 (4)0.019 (4)0.003 (3)0.007 (3)0.001 (3)
C80.035 (4)0.033 (4)0.037 (5)0.009 (4)0.004 (4)0.006 (4)
C90.034 (4)0.021 (4)0.035 (5)0.006 (3)0.006 (4)0.003 (3)
C100.034 (4)0.025 (4)0.019 (4)0.007 (3)0.004 (3)0.007 (3)
C110.027 (4)0.013 (3)0.027 (4)0.007 (3)0.007 (3)0.004 (3)
C120.029 (4)0.024 (4)0.029 (4)0.006 (3)0.018 (4)0.000 (3)
C130.023 (4)0.018 (4)0.030 (5)0.005 (3)0.012 (3)0.002 (3)
C140.031 (4)0.015 (4)0.038 (5)0.006 (3)0.008 (4)0.002 (3)
C150.018 (4)0.019 (4)0.032 (5)0.004 (3)0.001 (3)0.003 (3)
C160.024 (4)0.024 (4)0.037 (5)0.012 (3)0.004 (4)0.001 (4)
C170.023 (4)0.020 (4)0.047 (5)0.001 (3)0.005 (4)0.002 (4)
C180.029 (4)0.018 (4)0.029 (5)0.006 (3)0.008 (4)0.000 (3)
Geometric parameters (Å, º) top
Fe1—O11.881 (4)C4—C51.375 (9)
Fe1—O21.907 (5)C4—C171.481 (9)
Fe1—N12.086 (6)C5—C61.398 (8)
Fe1—N22.116 (6)C5—H50.9500
Fe1—Cl12.225 (3)C6—C71.453 (9)
O1—C11.315 (7)C7—H70.9500
O2—C161.332 (7)C8—C91.524 (9)
O3—C171.301 (8)C8—H8A0.9900
O3—H3O0.8400C8—H8B0.9900
O4—C171.233 (8)C9—H9A0.9900
O5—C181.317 (8)C9—H9B0.9900
O5—H5O0.8400C10—C111.445 (9)
O6—C181.223 (8)C10—H100.9500
N1—C71.298 (8)C11—C121.413 (8)
N1—C81.449 (9)C11—C161.427 (9)
N2—C101.282 (8)C12—C131.401 (9)
N2—C91.463 (8)C12—H120.9500
C1—C21.408 (9)C13—C141.405 (9)
C1—C61.419 (9)C13—C181.472 (9)
C2—C31.362 (9)C14—C151.367 (9)
C2—H20.9500C14—H140.9500
C3—C41.417 (9)C15—C161.389 (9)
C3—H30.9500C15—H150.9500
O1—Fe1—O295.1 (2)C6—C7—H7118.0
O1—Fe1—N187.3 (2)N1—C8—C9108.2 (6)
O2—Fe1—N1149.3 (2)N1—C8—H8A110.1
O1—Fe1—N2149.2 (2)C9—C8—H8A110.1
O2—Fe1—N285.4 (2)N1—C8—H8B110.1
N1—Fe1—N277.4 (2)C9—C8—H8B110.1
O1—Fe1—Cl1107.07 (16)H8A—C8—H8B108.4
O2—Fe1—Cl1102.90 (16)N2—C9—C8107.8 (6)
N1—Fe1—Cl1105.63 (18)N2—C9—H9A110.1
N2—Fe1—Cl1102.78 (17)C8—C9—H9A110.1
C1—O1—Fe1134.8 (4)N2—C9—H9B110.1
C16—O2—Fe1123.9 (5)C8—C9—H9B110.1
C17—O3—H3O109.5H9A—C9—H9B108.5
C18—O5—H5O109.5N2—C10—C11123.5 (6)
C7—N1—C8118.5 (6)N2—C10—H10118.3
C7—N1—Fe1127.6 (5)C11—C10—H10118.3
C8—N1—Fe1113.8 (4)C12—C11—C16118.5 (6)
C10—N2—C9120.9 (6)C12—C11—C10118.3 (6)
C10—N2—Fe1123.4 (5)C16—C11—C10123.1 (6)
C9—N2—Fe1115.7 (4)C13—C12—C11120.5 (7)
O1—C1—C2119.1 (6)C13—C12—H12119.7
O1—C1—C6122.3 (6)C11—C12—H12119.7
C2—C1—C6118.6 (6)C12—C13—C14119.2 (6)
C3—C2—C1121.2 (7)C12—C13—C18122.8 (6)
C3—C2—H2119.4C14—C13—C18117.9 (6)
C1—C2—H2119.4C15—C14—C13120.7 (7)
C2—C3—C4120.6 (6)C15—C14—H14119.6
C2—C3—H3119.7C13—C14—H14119.6
C4—C3—H3119.7C14—C15—C16121.2 (7)
C5—C4—C3118.5 (6)C14—C15—H15119.4
C5—C4—C17120.0 (6)C16—C15—H15119.4
C3—C4—C17121.4 (6)O2—C16—C15119.4 (6)
C4—C5—C6122.0 (6)O2—C16—C11120.8 (6)
C4—C5—H5119.0C15—C16—C11119.7 (6)
C6—C5—H5119.0O4—C17—O3123.3 (6)
C5—C6—C1118.9 (6)O4—C17—C4122.8 (7)
C5—C6—C7118.0 (6)O3—C17—C4113.9 (6)
C1—C6—C7123.1 (6)O6—C18—O5123.6 (6)
N1—C7—C6123.9 (6)O6—C18—C13120.7 (6)
N1—C7—H7118.0O5—C18—C13115.7 (6)
O2—Fe1—O1—C1159.6 (6)C2—C1—C6—C7179.8 (7)
N1—Fe1—O1—C110.3 (6)C8—N1—C7—C6179.1 (7)
N2—Fe1—O1—C170.0 (8)Fe1—N1—C7—C65.3 (10)
Cl1—Fe1—O1—C195.2 (6)C5—C6—C7—N1176.1 (7)
O1—Fe1—O2—C16162.6 (5)C1—C6—C7—N15.4 (11)
N1—Fe1—O2—C16104.2 (6)C7—N1—C8—C9134.0 (7)
N2—Fe1—O2—C1648.3 (5)Fe1—N1—C8—C942.2 (7)
Cl1—Fe1—O2—C1653.8 (5)C10—N2—C9—C8151.9 (6)
O1—Fe1—N1—C71.0 (6)Fe1—N2—C9—C826.6 (7)
O2—Fe1—N1—C796.4 (7)N1—C8—C9—N243.2 (8)
N2—Fe1—N1—C7154.1 (6)C9—N2—C10—C11175.4 (6)
Cl1—Fe1—N1—C7106.0 (6)Fe1—N2—C10—C116.2 (10)
O1—Fe1—N1—C8174.9 (5)N2—C10—C11—C12166.4 (6)
O2—Fe1—N1—C879.5 (7)N2—C10—C11—C1617.5 (11)
N2—Fe1—N1—C821.8 (5)C16—C11—C12—C132.4 (10)
Cl1—Fe1—N1—C878.2 (5)C10—C11—C12—C13178.6 (6)
O1—Fe1—N2—C10123.3 (6)C11—C12—C13—C142.4 (10)
O2—Fe1—N2—C1031.1 (6)C11—C12—C13—C18179.0 (6)
N1—Fe1—N2—C10174.5 (6)C12—C13—C14—C150.3 (10)
Cl1—Fe1—N2—C1071.1 (6)C18—C13—C14—C15176.5 (6)
O1—Fe1—N2—C958.2 (7)C13—C14—C15—C163.0 (11)
O2—Fe1—N2—C9150.4 (5)Fe1—O2—C16—C15142.0 (6)
N1—Fe1—N2—C93.9 (5)Fe1—O2—C16—C1141.2 (9)
Cl1—Fe1—N2—C9107.4 (5)C14—C15—C16—O2179.8 (7)
Fe1—O1—C1—C2170.2 (5)C14—C15—C16—C113.0 (11)
Fe1—O1—C1—C612.7 (11)C12—C11—C16—O2177.0 (6)
O1—C1—C2—C3177.0 (7)C10—C11—C16—O21.0 (11)
C6—C1—C2—C30.2 (11)C12—C11—C16—C150.3 (11)
C1—C2—C3—C41.1 (11)C10—C11—C16—C15175.7 (7)
C2—C3—C4—C51.0 (11)C5—C4—C17—O45.0 (12)
C2—C3—C4—C17178.8 (7)C3—C4—C17—O4175.2 (7)
C3—C4—C5—C60.5 (11)C5—C4—C17—O3174.0 (7)
C17—C4—C5—C6179.7 (7)C3—C4—C17—O35.8 (10)
C4—C5—C6—C11.8 (11)C12—C13—C18—O6172.5 (7)
C4—C5—C6—C7179.6 (7)C14—C13—C18—O64.1 (10)
O1—C1—C6—C5175.5 (6)C12—C13—C18—O55.7 (10)
C2—C1—C6—C51.7 (10)C14—C13—C18—O5177.6 (6)
O1—C1—C6—C73.1 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3O···O6i0.841.722.555 (6)172
O5—H5O···O4ii0.841.832.664 (6)171
Symmetry codes: (i) x+1, y1, z; (ii) x1, y+1, z.
 

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