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The crystal structure of the title compound, [Fe(C
6H
4NO
2)(C
6H
4.5NO
2)(C
6H
5NO
2)](BF
4)
0.5, is regarded as consisting of disordered mononuclear [Fe
II(C
6H
4.5NO
2)
3]
0.5+ cations and tetrafluoroborate anions. The
N,
O-chelated Fe lies on a special position of site symmetry 3 and the acid H atom on a special position of site symmetry
. The B atom is located on a special position of site symmetry
. The disordered mononuclear units are linked through the acid H atom into a layer motif.
Supporting information
CCDC reference: 608374
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.008 Å
- Disorder in solvent or counterion
- R factor = 0.065
- wR factor = 0.154
- Data-to-parameter ratio = 11.6
checkCIF/PLATON results
No syntax errors found
Alert level B
ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
Tmin and Tmax reported: 0.437 0.920
Tmin(prime) and Tmax expected: 0.862 0.919
RR(prime) = 0.506
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.50
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.39
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 57.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.31 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: C18 H13.5 B0.5 F2 Fe1 N3 O6
Atom count from _chemical_formula_moiety:
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
6 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
3 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.
Hemi{tris(picolinic acid-
κ2N,
O)iron(II)/tris(picolinato-
κ2N,
O)iron(II)} hemi(tetrafluoroborate)
top
Crystal data top
[Fe(C6H4NO2)(C6H4.5NO2)(C6H5NO2)](BF4)0.5 | Dx = 1.620 Mg m−3 |
Mr = 467.07 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, P3 | Cell parameters from 724 reflections |
Hall symbol: -P 3 | θ = 3.0–23.4° |
a = 13.564 (2) Å | µ = 0.85 mm−1 |
c = 6.0108 (9) Å | T = 295 K |
V = 957.7 (2) Å3 | Block, orange |
Z = 2 | 0.17 × 0.15 × 0.10 mm |
F(000) = 474 | |
Data collection top
Bruker APEX area-detector diffractometer | 1128 independent reflections |
Radiation source: fine-focus sealed tube | 1055 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
φ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→16 |
Tmin = 0.437, Tmax = 0.920 | k = −16→7 |
4988 measured reflections | l = −7→6 |
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H-atom parameters constrained |
S = 1.21 | w = 1/[σ2(Fo2) + (0.0655P)2 + 1.2441P] where P = (Fo2 + 2Fc2)/3 |
1128 reflections | (Δ/σ)max = 0.001 |
97 parameters | Δρmax = 0.74 e Å−3 |
6 restraints | Δρmin = −0.31 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Fe1 | 0.6667 | 0.3333 | 0.08941 (16) | 0.0306 (4) | |
F1 | 0.0971 (8) | 0.0162 (7) | 0.3730 (18) | 0.168 (4) | 0.67 |
O1 | 0.6008 (2) | 0.1833 (2) | 0.2873 (5) | 0.0378 (7) | |
O2 | 0.4535 (3) | 0.0092 (2) | 0.3321 (5) | 0.0484 (9) | |
N1 | 0.5135 (3) | 0.2122 (3) | −0.0838 (5) | 0.0306 (8) | |
C1 | 0.5068 (4) | 0.1033 (3) | 0.2321 (7) | 0.033 (1) | |
C2 | 0.4500 (4) | 0.1171 (3) | 0.0300 (7) | 0.036 (1) | |
C3 | 0.3413 (4) | 0.0387 (4) | −0.0314 (8) | 0.053 (1) | |
C4 | 0.2961 (5) | 0.0588 (5) | −0.221 (1) | 0.061 (2) | |
C5 | 0.3621 (5) | 0.1533 (4) | −0.3428 (8) | 0.053 (1) | |
C6 | 0.4707 (4) | 0.2298 (4) | −0.2692 (7) | 0.042 (1) | |
B1 | 0.0000 | 0.0000 | 0.5000 | 0.20 (1) | |
H2o | 0.4891 | 0.0105 | 0.4433 | 0.058* | 0.50 |
H3 | 0.2986 | −0.0267 | 0.0526 | 0.063* | |
H4 | 0.2217 | 0.0081 | −0.2640 | 0.074* | |
H5 | 0.3347 | 0.1667 | −0.4745 | 0.064* | |
H6 | 0.5153 | 0.2954 | −0.3516 | 0.050* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Fe1 | 0.0288 (4) | 0.0288 (4) | 0.0340 (6) | 0.0144 (2) | 0.000 | 0.000 |
F1 | 0.136 (7) | 0.083 (5) | 0.279 (12) | 0.051 (6) | −0.010 (7) | −0.009 (7) |
O1 | 0.038 (2) | 0.035 (2) | 0.038 (2) | 0.016 (1) | −0.006 (1) | 0.005 (1) |
O2 | 0.051 (2) | 0.031 (2) | 0.050 (2) | 0.010 (2) | −0.010 (2) | 0.012 (1) |
N1 | 0.036 (2) | 0.030 (2) | 0.029 (2) | 0.019 (2) | −0.002 (1) | 0.002 (1) |
C1 | 0.036 (2) | 0.028 (2) | 0.034 (2) | 0.015 (2) | −0.002 (2) | 0.002 (2) |
C2 | 0.040 (2) | 0.030 (2) | 0.036 (2) | 0.016 (2) | −0.007 (2) | −0.003 (2) |
C3 | 0.045 (3) | 0.037 (3) | 0.064 (3) | 0.011 (2) | −0.015 (2) | 0.002 (2) |
C4 | 0.048 (3) | 0.052 (3) | 0.073 (4) | 0.016 (3) | −0.025 (3) | −0.011 (3) |
C5 | 0.067 (3) | 0.059 (3) | 0.045 (3) | 0.040 (3) | −0.023 (2) | −0.010 (2) |
C6 | 0.057 (3) | 0.042 (3) | 0.035 (2) | 0.031 (2) | −0.003 (2) | 0.003 (2) |
B1 | 0.20 (1) | 0.20 (1) | 0.20 (2) | 0.099 (5) | 0.000 | 0.000 |
Geometric parameters (Å, º) top
Fe1—O1 | 2.130 (3) | C2—C3 | 1.368 (6) |
Fe1—O1i | 2.130 (3) | C3—C4 | 1.383 (7) |
Fe1—O1ii | 2.130 (3) | C4—C5 | 1.354 (8) |
Fe1—N1 | 2.165 (3) | C5—C6 | 1.384 (7) |
Fe1—N1i | 2.165 (3) | B1—F1iii | 1.441 (9) |
Fe1—N1ii | 2.165 (3) | B1—F1iv | 1.441 (9) |
F1—B1 | 1.441 (9) | B1—F1v | 1.441 (9) |
O1—C1 | 1.236 (5) | B1—F1vi | 1.441 (9) |
O2—C1 | 1.261 (5) | B1—F1vii | 1.441 (9) |
O2—H2o | 0.8200 | C3—H3 | 0.9300 |
N1—C2 | 1.327 (5) | C4—H4 | 0.9300 |
N1—C6 | 1.331 (5) | C5—H5 | 0.9300 |
C1—C2 | 1.500 (6) | C6—H6 | 0.9300 |
| | | |
O1—Fe1—O1i | 91.9 (1) | C4—C5—C6 | 119.2 (4) |
O1—Fe1—O1ii | 91.9 (1) | N1—C6—C5 | 122.0 (4) |
O1—Fe1—N1 | 76.0 (1) | F1iii—B1—F1iv | 94.5 (6) |
O1ii—Fe1—N1 | 94.3 (1) | F1iii—B1—F1v | 180.0 (7) |
O1—Fe1—N1ii | 166.5 (1) | F1iv—B1—F1v | 85.5 (6) |
O1i—Fe1—O1ii | 91.9 (1) | F1iii—B1—F1 | 85.5 (6) |
O1i—Fe1—N1i | 76.0 (1) | F1iv—B1—F1 | 85.5 (6) |
O1—Fe1—N1i | 94.3 (1) | F1v—B1—F1 | 94.5 (6) |
O1ii—Fe1—N1i | 166.5 (1) | F1iii—B1—F1vi | 85.5 (6) |
O1i—Fe1—N1 | 166.5 (1) | F1iv—B1—F1vi | 180.000 (1) |
O1i—Fe1—N1ii | 94.3 (1) | F1v—B1—F1vi | 94.5 (6) |
O1ii—Fe1—N1ii | 76.0 (1) | F1—B1—F1vi | 94.5 (6) |
N1—Fe1—N1i | 98.8 (1) | F1iii—B1—F1vii | 94.5 (6) |
N1—Fe1—N1ii | 98.8 (1) | F1iv—B1—F1vii | 94.5 (6) |
N1i—Fe1—N1ii | 98.8 (1) | F1v—B1—F1vii | 85.5 (6) |
C1—O1—Fe1 | 116.4 (2) | F1—B1—F1vii | 180.0 (4) |
C2—N1—C6 | 118.4 (4) | F1vi—B1—F1vii | 85.5 (6) |
C2—N1—Fe1 | 113.6 (2) | C1—O2—H2o | 109.5 |
C6—N1—Fe1 | 127.2 (3) | C2—C3—H3 | 120.6 |
O1—C1—O2 | 125.4 (4) | C4—C3—H3 | 120.6 |
O1—C1—C2 | 118.4 (4) | C5—C4—H4 | 120.5 |
O2—C1—C2 | 116.2 (4) | C3—C4—H4 | 120.5 |
N1—C2—C3 | 122.6 (4) | C4—C5—H5 | 120.4 |
N1—C2—C1 | 114.5 (3) | C6—C5—H5 | 120.4 |
C3—C2—C1 | 122.9 (4) | N1—C6—H6 | 119.0 |
C2—C3—C4 | 118.7 (5) | C5—C6—H6 | 119.0 |
C5—C4—C3 | 118.9 (5) | | |
| | | |
O1i—Fe1—O1—C1 | −180.0 (3) | Fe1—O1—C1—C2 | 1.9 (5) |
O1ii—Fe1—O1—C1 | 88.1 (4) | C6—N1—C2—C3 | −2.4 (6) |
N1i—Fe1—O1—C1 | −103.9 (3) | Fe1—N1—C2—C3 | 168.4 (4) |
N1—Fe1—O1—C1 | −5.9 (3) | C6—N1—C2—C1 | 178.2 (4) |
N1ii—Fe1—O1—C1 | 62.9 (6) | Fe1—N1—C2—C1 | −11.1 (4) |
O1i—Fe1—N1—C2 | 35.2 (7) | O1—C1—C2—N1 | 6.4 (6) |
O1—Fe1—N1—C2 | 9.2 (3) | O2—C1—C2—N1 | −173.4 (4) |
O1ii—Fe1—N1—C2 | −81.6 (3) | O1—C1—C2—C3 | −173.0 (4) |
N1i—Fe1—N1—C2 | 101.5 (3) | O2—C1—C2—C3 | 7.2 (6) |
N1ii—Fe1—N1—C2 | −158.1 (3) | N1—C2—C3—C4 | 0.7 (7) |
O1i—Fe1—N1—C6 | −155.0 (5) | C1—C2—C3—C4 | −179.9 (5) |
O1—Fe1—N1—C6 | 179.0 (4) | C2—C3—C4—C5 | 2.0 (8) |
O1ii—Fe1—N1—C6 | 88.2 (4) | C3—C4—C5—C6 | −2.9 (8) |
N1i—Fe1—N1—C6 | −88.8 (3) | C2—N1—C6—C5 | 1.4 (6) |
N1ii—Fe1—N1—C6 | 11.7 (4) | Fe1—N1—C6—C5 | −168.0 (3) |
Fe1—O1—C1—O2 | −178.3 (3) | C4—C5—C6—N1 | 1.3 (7) |
Symmetry codes: (i) −y+1, x−y, z; (ii) −x+y+1, −x+1, z; (iii) x−y, x, −z+1; (iv) y, −x+y, −z+1; (v) −x+y, −x, z; (vi) −y, x−y, z; (vii) −x, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2o···O2viii | 0.82 | 1.65 | 2.459 (6) | 171 |
Symmetry code: (viii) −x+1, −y, −z+1. |
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