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In the crystal structure of the title compound, [Fe(C8H4O4)(C3H7NO)]n, the FeII atom and the terephthalate group occupy special positions of 2/m site symmetry. The FeII atom is octa­hedrally coordinated: two O atoms of two dimethyl­formamide mol­ecules occupy the axial positions, and the equatorial sites are occupied by the carboxylate O atoms of four different terephthalate groups. The compound adopts a polymeric three-dimensional framework structure. The C and N atoms of the dimethylformamide ligand are disordered equally over two sites each, with further disorder of the H atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044091/bt2503sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044091/bt2503Isup2.hkl
Contains datablock I

CCDC reference: 663597

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.040
  • wR factor = 0.113
  • Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level A ABSTM02_ALERT_3_A The ratio of expected to reported Tmax/Tmin(RR') is < 0.50 Tmin and Tmax reported: 0.357 0.909 Tmin(prime) and Tmax expected: 0.733 0.907 RR(prime) = 0.486 Please check that your absorption correction is appropriate.
Author Response: The range is given by SADABS. A moderately heavy atom model is assumed.
PLAT061_ALERT_3_A Tmax/Tmin Range Test RR' too Large .............       0.48
Author Response: As above.

Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT076_ALERT_1_C Occupancy 0.50 less than 1.0 for Sp.pos . C4 PLAT076_ALERT_1_C Occupancy 0.50 less than 1.0 for Sp.pos . H4 PLAT076_ALERT_1_C Occupancy 0.50 less than 1.0 for Sp.pos . C5 PLAT076_ALERT_1_C Occupancy 0.50 less than 1.0 for Sp.pos . C6 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe1 PLAT301_ALERT_3_C Main Residue Disorder ......................... 15.00 Perc. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 29 C5 -N1 -C4 -O2 0.00 0.05 2.665 1.555 1.555 1.555 PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.11 Ratio
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C11 H11 Fe1 N1 O5 Atom count from _chemical_formula_moiety: PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

This study continues with the study on [(C8H4O4)(C3H7NO)Co]n (Fu et al., 2004; the present Fe(II) analog is isostructural with the Co(II) analog (Fu et al., 2004).

Related literature top

This FeII compound has the same structure as the CoII analogue (Fu et al., 2004).

Experimental top

Ferrous chloride tetrahydrate (0.198 g, 1 mmol), terephthalic acid (0.166 g, 1 mmol) and N,N-dimethylformamide (10 ml) were sealed in a 15-ml, Teflon-lined, stainless-steel bomb, which was heated at 433 K for 2 days. Red crystals were obtained when the bomb was cooled slowly to room temperature; yield 30% based on Fe.

Refinement top

The DMF molecule (comprising the O2, N1, C4, C5 and C6 atoms) lies on the Wyckoff 4 e site (of mm2 symmetry) and is disordered over two positions with respect to its carbon atoms only. As the disorder refined to almost 1/2, the occupancies of these carbon atoms was fixed as 1/4. The three N—C distances were restrained to within ±0.01 Å.

Hydrogen atoms were placed at calculated positions (C—H = 0.93 Å for the sp2 hybridized parent C atoms and 0.96 Å for the methyl C atoms) and were included in the refinements in the riding model approximation, with U(H) = 1.2Ueq for the aromatic H atoms and 1.5Ueq for the methyl H atoms. The two methyl groups were rotated so as to fit the electron density.

Structure description top

This study continues with the study on [(C8H4O4)(C3H7NO)Co]n (Fu et al., 2004; the present Fe(II) analog is isostructural with the Co(II) analog (Fu et al., 2004).

This FeII compound has the same structure as the CoII analogue (Fu et al., 2004).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: Atomic coordinates taken from Fu et al. (2004); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) plot of a portion of [Fe(C8H4O4)(C3H7NO)]n. Displacement ellipsoids are drawn at the 50% probability level, and H atoms are drawn as spheres of arbitrary radii. The disorder in the DMF molecules is not shown.
Poly[(µ2-N,N-dimethylformamide-κ2O:O) (µ4-terephthalato-κ4O:O':O'':O''')iron(II)] top
Crystal data top
[Fe(C8H4O4)(C3H7NO)]F(000) = 600
Mr = 293.06Dx = 1.558 Mg m3
Orthorhombic, ImmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 2b 2Cell parameters from 2096 reflections
a = 19.3652 (15) Åθ = 2.5–28.5°
b = 7.2856 (6) ŵ = 1.22 mm1
c = 8.8571 (7) ÅT = 295 K
V = 1249.62 (17) Å3Block, red
Z = 40.25 × 0.19 × 0.08 mm
Data collection top
Bruker APEX area-detector
diffractometer
791 independent reflections
Radiation source: fine-focus sealed tube730 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ and ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2524
Tmin = 0.357, Tmax = 0.909k = 97
3421 measured reflectionsl = 811
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0721P)2 + 1.8869P]
where P = (Fo2 + 2Fc2)/3
791 reflections(Δ/σ)max = 0.001
63 parametersΔρmax = 0.73 e Å3
3 restraintsΔρmin = 0.66 e Å3
Crystal data top
[Fe(C8H4O4)(C3H7NO)]V = 1249.62 (17) Å3
Mr = 293.06Z = 4
Orthorhombic, ImmaMo Kα radiation
a = 19.3652 (15) ŵ = 1.22 mm1
b = 7.2856 (6) ÅT = 295 K
c = 8.8571 (7) Å0.25 × 0.19 × 0.08 mm
Data collection top
Bruker APEX area-detector
diffractometer
791 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
730 reflections with I > 2σ(I)
Tmin = 0.357, Tmax = 0.909Rint = 0.021
3421 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0403 restraints
wR(F2) = 0.113H-atom parameters constrained
S = 1.08Δρmax = 0.73 e Å3
791 reflectionsΔρmin = 0.66 e Å3
63 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Fe10.50000.50000.50000.0209 (3)
O10.42136 (10)0.5968 (3)0.3639 (3)0.0461 (6)
O20.50000.75000.6390 (4)0.0333 (8)
N10.50000.75000.8974 (5)0.0533 (15)
C10.39343 (19)0.75000.3459 (5)0.0360 (8)
C20.31894 (19)0.75000.2960 (5)0.0390 (9)
C30.28393 (15)0.5876 (4)0.2733 (5)0.0630 (11)
H30.30640.47660.28960.076*
C40.5267 (4)0.75000.7594 (8)0.0380 (16)0.50
H40.57470.75000.75670.046*0.50
C50.5296 (7)0.75001.0396 (10)0.078 (4)0.50
H5A0.57760.78141.03150.117*0.25
H5B0.52520.63021.08370.117*0.25
H5C0.50660.83841.10220.117*0.25
C60.4266 (5)0.75000.9021 (13)0.088 (4)0.50
H6A0.41130.70100.99700.133*0.25
H6B0.40900.67560.82130.133*0.25
H6C0.40990.87340.89100.133*0.25
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0135 (4)0.0240 (4)0.0250 (4)0.0000.0000.0017 (2)
O10.0312 (9)0.0361 (11)0.0709 (13)0.0036 (8)0.0270 (9)0.0003 (9)
O20.044 (2)0.0279 (17)0.0279 (17)0.0000.0000.000
N10.084 (4)0.046 (3)0.029 (2)0.0000.0000.000
C10.0266 (17)0.0360 (19)0.045 (2)0.0000.0180 (15)0.000
C20.0261 (17)0.0346 (18)0.056 (2)0.0000.0204 (16)0.000
C30.0374 (17)0.0293 (14)0.122 (3)0.0040 (11)0.0381 (19)0.0023 (17)
C40.052 (4)0.029 (3)0.033 (3)0.0000.006 (3)0.000
C50.136 (13)0.068 (7)0.030 (4)0.0000.010 (6)0.000
C60.125 (12)0.094 (9)0.047 (6)0.0000.026 (7)0.000
Geometric parameters (Å, º) top
Fe1—O1i2.0663 (17)N1—C6iv1.422 (9)
Fe1—O1ii2.0663 (17)C1—O1v1.250 (2)
Fe1—O12.0663 (17)C1—C21.509 (5)
Fe1—O1iii2.0663 (17)C2—C31.378 (3)
Fe1—O22.199 (2)C2—C3v1.378 (3)
Fe1—O2i2.199 (2)C3—C3vi1.377 (5)
O1—C11.250 (2)C3—H30.9300
O2—C41.185 (8)C4—H40.9300
O2—C4iv1.185 (8)C5—H5A0.9600
O2—Fe1iv2.1987 (19)C5—H5B0.9600
N1—C4iv1.327 (7)C5—H5C0.9600
N1—C41.327 (7)C6—H6A0.9600
N1—C51.384 (8)C6—H6B0.9600
N1—C5iv1.384 (8)C6—H6C0.9600
N1—C61.422 (9)
O1i—Fe1—O1ii85.05 (13)C4iv—N1—C668.7 (6)
O1i—Fe1—O1180.0C4—N1—C6114.6 (7)
O1ii—Fe1—O194.95 (13)C5—N1—C6112.8 (8)
O1i—Fe1—O1iii94.95 (13)C5iv—N1—C663.9 (8)
O1ii—Fe1—O1iii180.00 (7)C4iv—N1—C6iv114.6 (7)
O1—Fe1—O1iii85.05 (13)C4—N1—C6iv68.7 (6)
O1i—Fe1—O287.49 (7)C5—N1—C6iv63.9 (8)
O1ii—Fe1—O292.51 (7)C5iv—N1—C6iv112.8 (8)
O1—Fe1—O292.51 (7)C6—N1—C6iv176.7 (10)
O1iii—Fe1—O287.49 (7)O1v—C1—O1126.4 (3)
O1i—Fe1—O2i92.51 (7)O1v—C1—C2116.81 (16)
O1ii—Fe1—O2i87.49 (7)O1—C1—C2116.81 (16)
O1—Fe1—O2i87.49 (7)C3—C2—C3v118.3 (3)
O1iii—Fe1—O2i92.51 (7)C3—C2—C1120.87 (17)
O2—Fe1—O2i180.0C3v—C2—C1120.87 (17)
C1—O1—Fe1134.27 (19)C3vi—C3—C2120.86 (17)
C4—O2—C4iv51.8 (8)C3vi—C3—H3119.6
C4—O2—Fe1120.26 (12)C2—C3—H3119.6
C4iv—O2—Fe1120.26 (12)O2—C4—N1131.1 (7)
C4—O2—Fe1iv120.26 (12)O2—C4—H4114.4
C4iv—O2—Fe1iv120.26 (12)N1—C4—H4114.4
Fe1—O2—Fe1iv111.87 (15)N1—C5—H5A109.5
C4iv—N1—C445.9 (7)N1—C5—H5B109.5
C4iv—N1—C5178.5 (7)N1—C5—H5C109.5
C4—N1—C5132.6 (6)N1—C6—H6A109.5
C4iv—N1—C5iv132.6 (6)N1—C6—H6B109.5
C4—N1—C5iv178.5 (7)N1—C6—H6C109.5
C5—N1—C5iv49.0 (12)
O1ii—Fe1—O1—C180.3 (4)Fe1—O1—C1—O1v29.3 (7)
O1iii—Fe1—O1—C199.7 (4)Fe1—O1—C1—C2151.3 (3)
O2—Fe1—O1—C112.5 (3)O1v—C1—C2—C3180.0 (4)
O2i—Fe1—O1—C1167.5 (3)O1—C1—C2—C30.6 (6)
O1i—Fe1—O2—C417.2 (4)O1v—C1—C2—C3v0.6 (6)
O1ii—Fe1—O2—C4102.1 (4)O1—C1—C2—C3v180.0 (4)
O1—Fe1—O2—C4162.8 (4)C3v—C2—C3—C3vi1.0 (10)
O1iii—Fe1—O2—C477.9 (4)C1—C2—C3—C3vi179.6 (5)
O1i—Fe1—O2—C4iv77.9 (5)C4iv—O2—C4—N10.0
O1ii—Fe1—O2—C4iv162.8 (4)Fe1—O2—C4—N1106.5 (2)
O1—Fe1—O2—C4iv102.1 (5)Fe1iv—O2—C4—N1106.5 (2)
O1iii—Fe1—O2—C4iv17.2 (4)C4iv—N1—C4—O20.0
O1i—Fe1—O2—Fe1iv132.46 (6)C5iv—N1—C4—O20.00 (5)
O1ii—Fe1—O2—Fe1iv47.54 (6)C6—N1—C4—O20.000 (2)
O1—Fe1—O2—Fe1iv47.54 (6)C6iv—N1—C4—O2180.000 (2)
O1iii—Fe1—O2—Fe1iv132.46 (6)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z; (iii) x, y+1, z+1; (iv) x+1, y+3/2, z; (v) x, y+3/2, z; (vi) x+1/2, y, z+1/2.

Experimental details

Crystal data
Chemical formula[Fe(C8H4O4)(C3H7NO)]
Mr293.06
Crystal system, space groupOrthorhombic, Imma
Temperature (K)295
a, b, c (Å)19.3652 (15), 7.2856 (6), 8.8571 (7)
V3)1249.62 (17)
Z4
Radiation typeMo Kα
µ (mm1)1.22
Crystal size (mm)0.25 × 0.19 × 0.08
Data collection
DiffractometerBruker APEX area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.357, 0.909
No. of measured, independent and
observed [I > 2σ(I)] reflections
3421, 791, 730
Rint0.021
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.113, 1.08
No. of reflections791
No. of parameters63
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.73, 0.66

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), Atomic coordinates taken from Fu et al. (2004), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).

 

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