Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044091/bt2503sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044091/bt2503Isup2.hkl |
CCDC reference: 663597
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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.
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.
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).
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).
[Fe(C8H4O4)(C3H7NO)] | F(000) = 600 |
Mr = 293.06 | Dx = 1.558 Mg m−3 |
Orthorhombic, Imma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -I 2b 2 | Cell parameters from 2096 reflections |
a = 19.3652 (15) Å | θ = 2.5–28.5° |
b = 7.2856 (6) Å | µ = 1.22 mm−1 |
c = 8.8571 (7) Å | T = 295 K |
V = 1249.62 (17) Å3 | Block, red |
Z = 4 | 0.25 × 0.19 × 0.08 mm |
Bruker APEX area-detector diffractometer | 791 independent reflections |
Radiation source: fine-focus sealed tube | 730 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
φ and ω scans | θmax = 27.5°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −25→24 |
Tmin = 0.357, Tmax = 0.909 | k = −9→7 |
3421 measured reflections | l = −8→11 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-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 parameters | Δρmax = 0.73 e Å−3 |
3 restraints | Δρmin = −0.66 e Å−3 |
[Fe(C8H4O4)(C3H7NO)] | V = 1249.62 (17) Å3 |
Mr = 293.06 | Z = 4 |
Orthorhombic, Imma | Mo Kα radiation |
a = 19.3652 (15) Å | µ = 1.22 mm−1 |
b = 7.2856 (6) Å | T = 295 K |
c = 8.8571 (7) Å | 0.25 × 0.19 × 0.08 mm |
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 = 0.909 | Rint = 0.021 |
3421 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 3 restraints |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.73 e Å−3 |
791 reflections | Δρmin = −0.66 e Å−3 |
63 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Fe1 | 0.5000 | 0.5000 | 0.5000 | 0.0209 (3) | |
O1 | 0.42136 (10) | 0.5968 (3) | 0.3639 (3) | 0.0461 (6) | |
O2 | 0.5000 | 0.7500 | 0.6390 (4) | 0.0333 (8) | |
N1 | 0.5000 | 0.7500 | 0.8974 (5) | 0.0533 (15) | |
C1 | 0.39343 (19) | 0.7500 | 0.3459 (5) | 0.0360 (8) | |
C2 | 0.31894 (19) | 0.7500 | 0.2960 (5) | 0.0390 (9) | |
C3 | 0.28393 (15) | 0.5876 (4) | 0.2733 (5) | 0.0630 (11) | |
H3 | 0.3064 | 0.4766 | 0.2896 | 0.076* | |
C4 | 0.5267 (4) | 0.7500 | 0.7594 (8) | 0.0380 (16) | 0.50 |
H4 | 0.5747 | 0.7500 | 0.7567 | 0.046* | 0.50 |
C5 | 0.5296 (7) | 0.7500 | 1.0396 (10) | 0.078 (4) | 0.50 |
H5A | 0.5776 | 0.7814 | 1.0315 | 0.117* | 0.25 |
H5B | 0.5252 | 0.6302 | 1.0837 | 0.117* | 0.25 |
H5C | 0.5066 | 0.8384 | 1.1022 | 0.117* | 0.25 |
C6 | 0.4266 (5) | 0.7500 | 0.9021 (13) | 0.088 (4) | 0.50 |
H6A | 0.4113 | 0.7010 | 0.9970 | 0.133* | 0.25 |
H6B | 0.4090 | 0.6756 | 0.8213 | 0.133* | 0.25 |
H6C | 0.4099 | 0.8734 | 0.8910 | 0.133* | 0.25 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.0135 (4) | 0.0240 (4) | 0.0250 (4) | 0.000 | 0.000 | 0.0017 (2) |
O1 | 0.0312 (9) | 0.0361 (11) | 0.0709 (13) | 0.0036 (8) | −0.0270 (9) | 0.0003 (9) |
O2 | 0.044 (2) | 0.0279 (17) | 0.0279 (17) | 0.000 | 0.000 | 0.000 |
N1 | 0.084 (4) | 0.046 (3) | 0.029 (2) | 0.000 | 0.000 | 0.000 |
C1 | 0.0266 (17) | 0.0360 (19) | 0.045 (2) | 0.000 | −0.0180 (15) | 0.000 |
C2 | 0.0261 (17) | 0.0346 (18) | 0.056 (2) | 0.000 | −0.0204 (16) | 0.000 |
C3 | 0.0374 (17) | 0.0293 (14) | 0.122 (3) | 0.0040 (11) | −0.0381 (19) | 0.0023 (17) |
C4 | 0.052 (4) | 0.029 (3) | 0.033 (3) | 0.000 | −0.006 (3) | 0.000 |
C5 | 0.136 (13) | 0.068 (7) | 0.030 (4) | 0.000 | −0.010 (6) | 0.000 |
C6 | 0.125 (12) | 0.094 (9) | 0.047 (6) | 0.000 | 0.026 (7) | 0.000 |
Fe1—O1i | 2.0663 (17) | N1—C6iv | 1.422 (9) |
Fe1—O1ii | 2.0663 (17) | C1—O1v | 1.250 (2) |
Fe1—O1 | 2.0663 (17) | C1—C2 | 1.509 (5) |
Fe1—O1iii | 2.0663 (17) | C2—C3 | 1.378 (3) |
Fe1—O2 | 2.199 (2) | C2—C3v | 1.378 (3) |
Fe1—O2i | 2.199 (2) | C3—C3vi | 1.377 (5) |
O1—C1 | 1.250 (2) | C3—H3 | 0.9300 |
O2—C4 | 1.185 (8) | C4—H4 | 0.9300 |
O2—C4iv | 1.185 (8) | C5—H5A | 0.9600 |
O2—Fe1iv | 2.1987 (19) | C5—H5B | 0.9600 |
N1—C4iv | 1.327 (7) | C5—H5C | 0.9600 |
N1—C4 | 1.327 (7) | C6—H6A | 0.9600 |
N1—C5 | 1.384 (8) | C6—H6B | 0.9600 |
N1—C5iv | 1.384 (8) | C6—H6C | 0.9600 |
N1—C6 | 1.422 (9) | ||
O1i—Fe1—O1ii | 85.05 (13) | C4iv—N1—C6 | 68.7 (6) |
O1i—Fe1—O1 | 180.0 | C4—N1—C6 | 114.6 (7) |
O1ii—Fe1—O1 | 94.95 (13) | C5—N1—C6 | 112.8 (8) |
O1i—Fe1—O1iii | 94.95 (13) | C5iv—N1—C6 | 63.9 (8) |
O1ii—Fe1—O1iii | 180.00 (7) | C4iv—N1—C6iv | 114.6 (7) |
O1—Fe1—O1iii | 85.05 (13) | C4—N1—C6iv | 68.7 (6) |
O1i—Fe1—O2 | 87.49 (7) | C5—N1—C6iv | 63.9 (8) |
O1ii—Fe1—O2 | 92.51 (7) | C5iv—N1—C6iv | 112.8 (8) |
O1—Fe1—O2 | 92.51 (7) | C6—N1—C6iv | 176.7 (10) |
O1iii—Fe1—O2 | 87.49 (7) | O1v—C1—O1 | 126.4 (3) |
O1i—Fe1—O2i | 92.51 (7) | O1v—C1—C2 | 116.81 (16) |
O1ii—Fe1—O2i | 87.49 (7) | O1—C1—C2 | 116.81 (16) |
O1—Fe1—O2i | 87.49 (7) | C3—C2—C3v | 118.3 (3) |
O1iii—Fe1—O2i | 92.51 (7) | C3—C2—C1 | 120.87 (17) |
O2—Fe1—O2i | 180.0 | C3v—C2—C1 | 120.87 (17) |
C1—O1—Fe1 | 134.27 (19) | C3vi—C3—C2 | 120.86 (17) |
C4—O2—C4iv | 51.8 (8) | C3vi—C3—H3 | 119.6 |
C4—O2—Fe1 | 120.26 (12) | C2—C3—H3 | 119.6 |
C4iv—O2—Fe1 | 120.26 (12) | O2—C4—N1 | 131.1 (7) |
C4—O2—Fe1iv | 120.26 (12) | O2—C4—H4 | 114.4 |
C4iv—O2—Fe1iv | 120.26 (12) | N1—C4—H4 | 114.4 |
Fe1—O2—Fe1iv | 111.87 (15) | N1—C5—H5A | 109.5 |
C4iv—N1—C4 | 45.9 (7) | N1—C5—H5B | 109.5 |
C4iv—N1—C5 | 178.5 (7) | N1—C5—H5C | 109.5 |
C4—N1—C5 | 132.6 (6) | N1—C6—H6A | 109.5 |
C4iv—N1—C5iv | 132.6 (6) | N1—C6—H6B | 109.5 |
C4—N1—C5iv | 178.5 (7) | N1—C6—H6C | 109.5 |
C5—N1—C5iv | 49.0 (12) | ||
O1ii—Fe1—O1—C1 | −80.3 (4) | Fe1—O1—C1—O1v | 29.3 (7) |
O1iii—Fe1—O1—C1 | 99.7 (4) | Fe1—O1—C1—C2 | −151.3 (3) |
O2—Fe1—O1—C1 | 12.5 (3) | O1v—C1—C2—C3 | 180.0 (4) |
O2i—Fe1—O1—C1 | −167.5 (3) | O1—C1—C2—C3 | 0.6 (6) |
O1i—Fe1—O2—C4 | −17.2 (4) | O1v—C1—C2—C3v | −0.6 (6) |
O1ii—Fe1—O2—C4 | −102.1 (4) | O1—C1—C2—C3v | 180.0 (4) |
O1—Fe1—O2—C4 | 162.8 (4) | C3v—C2—C3—C3vi | 1.0 (10) |
O1iii—Fe1—O2—C4 | 77.9 (4) | C1—C2—C3—C3vi | −179.6 (5) |
O1i—Fe1—O2—C4iv | −77.9 (5) | C4iv—O2—C4—N1 | 0.0 |
O1ii—Fe1—O2—C4iv | −162.8 (4) | Fe1—O2—C4—N1 | −106.5 (2) |
O1—Fe1—O2—C4iv | 102.1 (5) | Fe1iv—O2—C4—N1 | 106.5 (2) |
O1iii—Fe1—O2—C4iv | 17.2 (4) | C4iv—N1—C4—O2 | 0.0 |
O1i—Fe1—O2—Fe1iv | 132.46 (6) | C5iv—N1—C4—O2 | 0.00 (5) |
O1ii—Fe1—O2—Fe1iv | 47.54 (6) | C6—N1—C4—O2 | 0.000 (2) |
O1—Fe1—O2—Fe1iv | −47.54 (6) | C6iv—N1—C4—O2 | 180.000 (2) |
O1iii—Fe1—O2—Fe1iv | −132.46 (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)] |
Mr | 293.06 |
Crystal system, space group | Orthorhombic, Imma |
Temperature (K) | 295 |
a, b, c (Å) | 19.3652 (15), 7.2856 (6), 8.8571 (7) |
V (Å3) | 1249.62 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.22 |
Crystal size (mm) | 0.25 × 0.19 × 0.08 |
Data collection | |
Diffractometer | Bruker APEX area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.357, 0.909 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3421, 791, 730 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.113, 1.08 |
No. of reflections | 791 |
No. of parameters | 63 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
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).