Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042122/bi2233sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042122/bi2233Isup2.hkl |
CCDC reference: 1296678
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.036
- wR factor = 0.100
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Fe1
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT794_ALERT_5_G Check Predicted Bond Valency for Fe1 (2) 2.13 PLAT794_ALERT_5_G Check Predicted Bond Valency for Fe2 (2) 2.15 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 2 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
For related literature, see: Li et al. (1993); Go et al. (2004); An et al. (2000); Baroni et al. (1996); Hundal et al. (2002).
A mixture of FeSO4 (0.1 mmol), imidazole-4,5-dicarboxylic acid (0.1 mmol) and 2,2'-bipyridine (0.1 mmol) in 10 ml of a mixed ethanol/water solvent (1:1) was placed in a 25 ml Teflon-lined stainless steel autoclave and kept at 473 K for 10 d. Green crystals of the title compound were obtained after cooling to room temperature with a yield of 5%. Elemental analysis calculated: C 49.18, H 2.73, N 7.65%; found: C 49.12, H 2.77, N 7.61%.
H atoms bound to C atoms were placed geometrically and refined as riding atoms with C—H= 0.93 Å and with Uiso(H) = 1.2Ueq(C). The H atom on O1 was also placed geometrically and refined as riding atom with O—H = 0.82 Å and with Uiso(H) = 1.5Ueq(O). The H atom on O6 was located in a difference Fourier map and refined with O—H restrained to be 0.82 (1) Å and with Uiso(H) = 1.5Ueq(O).
Complexes containing carboxylic acids are of interest to chemists on account of their potential applications, such as catalysis, optics, information storage, medicine, molecular electrochemistry, biochemistry and biological pharmaceutics (Li et al., 1993; Go et al., 2004). Thus far, N-containing aromatic carboxylic acids, for example adipiodone and acetrizoic acid, have been widely used in organic synthesis, as dye intermediates, sensitization materials and functional pigments (An et al., 2000). Pyridine carboxylic acid is also used extensively in coordination chemistry due to its strong coordinating ability and versatile coordination modes (Baroni et al. (1996); Hundal et al. (2002)).
In the title compound, the asymetric unit contains two crystallographically independent monomer units. As shown in Fig. 1, FeII atoms have a distorted octahedral geometry formed by two carboxylate O atoms and four N atoms, two of which belong to the 2,2'-bipyridine ligand and the other two to the imidazole ring. The Fe—O and Fe—N bond lengths are in the range 2.110 (2)–2.216 (2) and 2.071 (2)–2.296 (2) Å, respectively. The carboxy and carboxylate groups of the 5-carboxy-4-carboxylatoimidazol-1-ide ligand coordinate in a monodentate fashion to two FeII atoms, giving rise to one-dimensional zigzag chains along [010] (Fig. 2). The 2,2'-bipyridine ligands are situated between these chains.
For related literature, see: Li et al. (1993); Go et al. (2004); An et al. (2000); Baroni et al. (1996); Hundal et al. (2002).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).
[Fe(C5H2N2O4)(C10H8N2)] | F(000) = 1488 |
Mr = 366.12 | Dx = 1.743 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5866 reflections |
a = 19.9862 (10) Å | θ = 2.3–26.7° |
b = 9.8828 (5) Å | µ = 1.11 mm−1 |
c = 14.4351 (7) Å | T = 293 K |
β = 101.806 (1)° | Block, green |
V = 2790.9 (2) Å3 | 0.43 × 0.35 × 0.28 mm |
Z = 8 |
Bruker APEXII CCD area-detector diffractometer | 5866 independent reflections |
Radiation source: fine-focus sealed tube | 4863 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
φ and ω scans | θmax = 26.7°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −25→20 |
Tmin = 0.647, Tmax = 0.746 | k = −11→10 |
15091 measured reflections | l = −17→18 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.061P)2 + 2.1242P] where P = (Fo2 + 2Fc2)/3 |
5866 reflections | (Δ/σ)max < 0.001 |
437 parameters | Δρmax = 0.44 e Å−3 |
1 restraint | Δρmin = −0.49 e Å−3 |
[Fe(C5H2N2O4)(C10H8N2)] | V = 2790.9 (2) Å3 |
Mr = 366.12 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 19.9862 (10) Å | µ = 1.11 mm−1 |
b = 9.8828 (5) Å | T = 293 K |
c = 14.4351 (7) Å | 0.43 × 0.35 × 0.28 mm |
β = 101.806 (1)° |
Bruker APEXII CCD area-detector diffractometer | 5866 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 4863 reflections with I > 2σ(I) |
Tmin = 0.647, Tmax = 0.746 | Rint = 0.027 |
15091 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 1 restraint |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.44 e Å−3 |
5866 reflections | Δρmin = −0.49 e Å−3 |
437 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.25412 (13) | −0.1015 (3) | 0.11260 (18) | 0.0286 (6) | |
C2 | 0.18886 (14) | −0.1492 (3) | 0.09414 (19) | 0.0336 (6) | |
H2 | 0.1524 | −0.0904 | 0.0745 | 0.040* | |
C3 | 0.17701 (14) | −0.2887 (3) | 0.1050 (2) | 0.0357 (6) | |
H3 | 0.1325 | −0.3220 | 0.0911 | 0.043* | |
C4 | 0.23018 (15) | −0.3752 (3) | 0.13573 (19) | 0.0335 (6) | |
H4 | 0.2231 | −0.4671 | 0.1437 | 0.040* | |
C5 | 0.29390 (14) | −0.3204 (3) | 0.15413 (19) | 0.0318 (6) | |
H5 | 0.3310 | −0.3771 | 0.1754 | 0.038* | |
C6 | 0.27142 (13) | 0.0457 (3) | 0.09936 (18) | 0.0287 (6) | |
C7 | 0.22341 (14) | 0.1449 (3) | 0.06224 (19) | 0.0338 (6) | |
H7 | 0.1774 | 0.1219 | 0.0452 | 0.041* | |
C8 | 0.24383 (15) | 0.2782 (3) | 0.0504 (2) | 0.0365 (6) | |
H8 | 0.2116 | 0.3439 | 0.0266 | 0.044* | |
C9 | 0.31112 (15) | 0.3106 (3) | 0.0741 (2) | 0.0371 (6) | |
H9 | 0.3266 | 0.3978 | 0.0665 | 0.045* | |
C10 | 0.35557 (14) | 0.2074 (3) | 0.1101 (2) | 0.0355 (6) | |
H10 | 0.4019 | 0.2281 | 0.1267 | 0.043* | |
C11 | 0.52108 (13) | 0.1314 (3) | 0.22142 (18) | 0.0281 (5) | |
H11 | 0.5347 | 0.1320 | 0.1635 | 0.034* | |
C12 | 0.51363 (13) | 0.1848 (3) | 0.35977 (18) | 0.0270 (5) | |
C13 | 0.47003 (13) | 0.0770 (3) | 0.32962 (18) | 0.0265 (5) | |
C14 | 0.41974 (13) | 0.0067 (3) | 0.37172 (19) | 0.0289 (6) | |
C15 | 0.52678 (13) | 0.2659 (3) | 0.44617 (18) | 0.0286 (6) | |
C16 | 0.24864 (14) | −0.0084 (3) | 0.85456 (18) | 0.0305 (6) | |
C17 | 0.31616 (15) | 0.0270 (3) | 0.8779 (2) | 0.0417 (7) | |
H17 | 0.3489 | −0.0364 | 0.9043 | 0.050* | |
C18 | 0.33542 (16) | 0.1596 (4) | 0.8615 (2) | 0.0486 (8) | |
H18 | 0.3814 | 0.1833 | 0.8768 | 0.058* | |
C19 | 0.28792 (15) | 0.2557 (3) | 0.8235 (2) | 0.0424 (7) | |
H19 | 0.3004 | 0.3435 | 0.8115 | 0.051* | |
C20 | 0.22184 (14) | 0.2149 (3) | 0.80465 (19) | 0.0342 (6) | |
H20 | 0.1882 | 0.2775 | 0.7799 | 0.041* | |
C21 | 0.22464 (13) | −0.1523 (3) | 0.86056 (18) | 0.0305 (6) | |
C22 | 0.26600 (16) | −0.2602 (3) | 0.8977 (2) | 0.0392 (7) | |
H22 | 0.3119 | −0.2446 | 0.9239 | 0.047* | |
C23 | 0.24014 (18) | −0.3919 (3) | 0.8965 (2) | 0.0468 (8) | |
H23 | 0.2684 | −0.4631 | 0.9221 | 0.056* | |
C24 | 0.17451 (17) | −0.4144 (3) | 0.8583 (2) | 0.0445 (8) | |
H24 | 0.1555 | −0.5004 | 0.8568 | 0.053* | |
C25 | 0.13582 (16) | −0.3022 (3) | 0.8205 (2) | 0.0377 (7) | |
H25 | 0.0902 | −0.3166 | 0.7924 | 0.045* | |
C26 | 0.06717 (13) | 0.1530 (3) | 0.60594 (17) | 0.0280 (5) | |
C27 | 0.04097 (12) | 0.2468 (3) | 0.66939 (17) | 0.0251 (5) | |
C28 | −0.00283 (13) | 0.3567 (3) | 0.65276 (17) | 0.0254 (5) | |
C29 | 0.02308 (13) | 0.3216 (3) | 0.79865 (17) | 0.0267 (5) | |
H29 | 0.0255 | 0.3308 | 0.8634 | 0.032* | |
C30 | −0.04275 (12) | 0.4138 (3) | 0.56638 (17) | 0.0248 (5) | |
Fe1 | 0.100575 (14) | 0.02478 (3) | 0.78559 (2) | 0.01296 (10) | |
Fe2 | 0.402091 (15) | −0.09584 (3) | 0.18027 (2) | 0.01510 (10) | |
N1 | 0.47565 (11) | 0.0429 (2) | 0.24137 (15) | 0.0275 (5) | |
N2 | 0.05700 (11) | 0.2242 (2) | 0.76226 (14) | 0.0265 (5) | |
N3 | 0.33654 (11) | 0.0779 (2) | 0.12307 (16) | 0.0298 (5) | |
N4 | 0.30592 (11) | −0.1867 (2) | 0.14295 (15) | 0.0296 (5) | |
N5 | 0.20255 (11) | 0.0867 (2) | 0.82027 (15) | 0.0295 (5) | |
N6 | 0.15995 (11) | −0.1735 (2) | 0.82203 (16) | 0.0316 (5) | |
N7 | −0.01405 (11) | 0.4035 (2) | 0.73571 (14) | 0.0263 (5) | |
N8 | 0.54562 (11) | 0.2190 (2) | 0.29037 (15) | 0.0282 (5) | |
O1 | 0.41577 (10) | 0.0408 (2) | 0.45503 (14) | 0.0355 (5) | |
H1 | 0.4462 | 0.0953 | 0.4756 | 0.053* | |
O2 | 0.38175 (10) | −0.0777 (2) | 0.32461 (14) | 0.0343 (4) | |
O3 | 0.56775 (10) | 0.3637 (2) | 0.45259 (13) | 0.0344 (4) | |
O4 | 0.49475 (10) | 0.2334 (2) | 0.50895 (13) | 0.0364 (5) | |
O5 | −0.08546 (9) | 0.50345 (19) | 0.57110 (12) | 0.0285 (4) | |
O6 | −0.03321 (9) | 0.3645 (2) | 0.48931 (12) | 0.0310 (4) | |
O7 | 0.05428 (11) | 0.1818 (2) | 0.52042 (13) | 0.0394 (5) | |
O8 | 0.10133 (10) | 0.0515 (2) | 0.64077 (13) | 0.0313 (4) | |
H6 | −0.0001 (13) | 0.314 (2) | 0.499 (3) | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0262 (13) | 0.0346 (15) | 0.0241 (12) | 0.0017 (11) | 0.0032 (10) | 0.0001 (10) |
C2 | 0.0277 (14) | 0.0376 (16) | 0.0337 (14) | −0.0009 (12) | 0.0019 (11) | 0.0051 (12) |
C3 | 0.0272 (14) | 0.0438 (17) | 0.0343 (14) | −0.0068 (12) | 0.0021 (11) | 0.0025 (13) |
C4 | 0.0366 (15) | 0.0313 (15) | 0.0321 (13) | −0.0073 (12) | 0.0058 (11) | 0.0017 (12) |
C5 | 0.0311 (14) | 0.0298 (15) | 0.0337 (13) | 0.0003 (11) | 0.0045 (11) | 0.0017 (11) |
C6 | 0.0253 (13) | 0.0333 (15) | 0.0264 (12) | −0.0007 (11) | 0.0029 (10) | −0.0005 (11) |
C7 | 0.0269 (14) | 0.0398 (16) | 0.0326 (14) | 0.0028 (12) | 0.0014 (11) | 0.0001 (12) |
C8 | 0.0363 (15) | 0.0330 (16) | 0.0376 (15) | 0.0077 (12) | 0.0012 (12) | 0.0046 (12) |
C9 | 0.0390 (16) | 0.0301 (15) | 0.0416 (15) | −0.0019 (12) | 0.0066 (13) | 0.0039 (12) |
C10 | 0.0288 (14) | 0.0375 (16) | 0.0393 (15) | −0.0041 (12) | 0.0049 (11) | 0.0021 (13) |
C11 | 0.0240 (12) | 0.0339 (15) | 0.0259 (12) | −0.0025 (11) | 0.0037 (10) | −0.0004 (11) |
C12 | 0.0220 (12) | 0.0312 (14) | 0.0269 (12) | 0.0020 (10) | 0.0029 (10) | 0.0012 (11) |
C13 | 0.0232 (12) | 0.0297 (14) | 0.0255 (12) | 0.0040 (10) | 0.0025 (10) | 0.0005 (10) |
C14 | 0.0244 (13) | 0.0310 (14) | 0.0306 (13) | 0.0036 (11) | 0.0042 (10) | −0.0001 (11) |
C15 | 0.0239 (12) | 0.0309 (14) | 0.0290 (13) | 0.0030 (11) | 0.0010 (10) | 0.0001 (11) |
C16 | 0.0258 (13) | 0.0412 (16) | 0.0234 (12) | 0.0041 (12) | 0.0028 (10) | −0.0005 (11) |
C17 | 0.0256 (14) | 0.054 (2) | 0.0430 (16) | 0.0045 (13) | 0.0014 (12) | −0.0012 (14) |
C18 | 0.0258 (15) | 0.062 (2) | 0.0547 (19) | −0.0096 (15) | 0.0009 (13) | −0.0088 (17) |
C19 | 0.0357 (16) | 0.0442 (18) | 0.0468 (17) | −0.0089 (14) | 0.0073 (13) | −0.0026 (14) |
C20 | 0.0318 (14) | 0.0337 (16) | 0.0356 (14) | −0.0034 (12) | 0.0033 (11) | −0.0003 (12) |
C21 | 0.0268 (13) | 0.0417 (16) | 0.0239 (12) | 0.0055 (12) | 0.0072 (10) | 0.0032 (11) |
C22 | 0.0341 (15) | 0.0472 (19) | 0.0364 (15) | 0.0117 (13) | 0.0076 (12) | 0.0069 (13) |
C23 | 0.0469 (19) | 0.045 (2) | 0.0507 (18) | 0.0204 (15) | 0.0159 (15) | 0.0115 (15) |
C24 | 0.0488 (19) | 0.0328 (17) | 0.0558 (19) | 0.0067 (14) | 0.0194 (16) | 0.0039 (14) |
C25 | 0.0383 (16) | 0.0338 (16) | 0.0441 (16) | 0.0028 (13) | 0.0157 (13) | 0.0014 (13) |
C26 | 0.0256 (13) | 0.0311 (14) | 0.0267 (12) | 0.0015 (11) | 0.0041 (10) | 0.0007 (11) |
C27 | 0.0220 (12) | 0.0289 (14) | 0.0239 (11) | −0.0013 (10) | 0.0036 (9) | 0.0015 (10) |
C28 | 0.0239 (12) | 0.0278 (13) | 0.0243 (11) | −0.0019 (10) | 0.0042 (9) | −0.0007 (10) |
C29 | 0.0272 (13) | 0.0320 (14) | 0.0205 (11) | 0.0009 (11) | 0.0041 (9) | 0.0005 (10) |
C30 | 0.0220 (12) | 0.0274 (14) | 0.0247 (12) | −0.0016 (10) | 0.0045 (10) | −0.0007 (10) |
Fe1 | 0.00936 (16) | 0.01382 (18) | 0.01510 (16) | 0.00017 (11) | 0.00110 (11) | 0.00294 (11) |
Fe2 | 0.00912 (16) | 0.01409 (18) | 0.01998 (17) | 0.00012 (11) | −0.00194 (12) | −0.00090 (12) |
N1 | 0.0225 (11) | 0.0331 (13) | 0.0258 (10) | 0.0005 (9) | 0.0022 (8) | −0.0010 (9) |
N2 | 0.0255 (11) | 0.0296 (12) | 0.0237 (10) | 0.0010 (9) | 0.0036 (8) | 0.0018 (9) |
N3 | 0.0246 (11) | 0.0315 (12) | 0.0322 (11) | −0.0007 (9) | 0.0034 (9) | 0.0022 (10) |
N4 | 0.0253 (11) | 0.0337 (13) | 0.0282 (11) | −0.0011 (9) | 0.0018 (9) | 0.0008 (9) |
N5 | 0.0233 (11) | 0.0382 (14) | 0.0270 (11) | 0.0002 (9) | 0.0049 (9) | 0.0010 (9) |
N6 | 0.0287 (12) | 0.0343 (13) | 0.0323 (11) | 0.0042 (10) | 0.0075 (9) | 0.0014 (10) |
N7 | 0.0258 (11) | 0.0298 (12) | 0.0227 (10) | 0.0009 (9) | 0.0031 (8) | −0.0003 (9) |
N8 | 0.0251 (11) | 0.0325 (12) | 0.0263 (11) | −0.0008 (9) | 0.0035 (8) | 0.0009 (9) |
O1 | 0.0325 (11) | 0.0430 (13) | 0.0332 (10) | −0.0032 (9) | 0.0116 (8) | −0.0016 (9) |
O2 | 0.0266 (10) | 0.0404 (11) | 0.0366 (10) | −0.0060 (8) | 0.0078 (8) | −0.0017 (9) |
O3 | 0.0307 (10) | 0.0383 (11) | 0.0321 (10) | −0.0033 (9) | 0.0015 (8) | −0.0053 (8) |
O4 | 0.0373 (11) | 0.0437 (12) | 0.0287 (10) | −0.0003 (9) | 0.0078 (8) | −0.0035 (9) |
O5 | 0.0247 (9) | 0.0341 (10) | 0.0259 (9) | 0.0044 (8) | 0.0034 (7) | 0.0022 (8) |
O6 | 0.0297 (10) | 0.0377 (11) | 0.0243 (9) | 0.0053 (8) | 0.0026 (7) | 0.0014 (8) |
O7 | 0.0485 (12) | 0.0471 (13) | 0.0234 (9) | 0.0151 (10) | 0.0089 (8) | 0.0011 (9) |
O8 | 0.0323 (10) | 0.0328 (10) | 0.0293 (9) | 0.0077 (8) | 0.0077 (8) | 0.0016 (8) |
C1—N4 | 1.337 (3) | C20—N5 | 1.357 (4) |
C1—C2 | 1.361 (4) | C20—H20 | 0.930 |
C1—C6 | 1.517 (4) | C21—N6 | 1.316 (3) |
C2—C3 | 1.413 (4) | C21—C22 | 1.388 (4) |
C2—H2 | 0.930 | C22—C23 | 1.400 (5) |
C3—C4 | 1.365 (4) | C22—H22 | 0.930 |
C3—H3 | 0.930 | C23—C24 | 1.333 (5) |
C4—C5 | 1.359 (4) | C23—H23 | 0.930 |
C4—H4 | 0.930 | C24—C25 | 1.397 (4) |
C5—N4 | 1.358 (4) | C24—H24 | 0.930 |
C5—H5 | 0.930 | C25—N6 | 1.358 (4) |
C6—N3 | 1.315 (3) | C25—H25 | 0.930 |
C6—C7 | 1.399 (4) | C26—O7 | 1.241 (3) |
C7—C8 | 1.400 (4) | C26—O8 | 1.259 (3) |
C7—H7 | 0.930 | C26—C27 | 1.473 (4) |
C8—C9 | 1.357 (4) | C27—N2 | 1.332 (3) |
C8—H8 | 0.930 | C27—C28 | 1.384 (4) |
C9—C10 | 1.382 (4) | C28—N7 | 1.345 (3) |
C9—H9 | 0.930 | C28—C30 | 1.450 (3) |
C10—N3 | 1.359 (4) | C29—N7 | 1.325 (3) |
C10—H10 | 0.930 | C29—N2 | 1.345 (3) |
C11—N1 | 1.334 (3) | C29—H29 | 0.930 |
C11—N8 | 1.334 (3) | C30—O5 | 1.242 (3) |
C11—H11 | 0.930 | C30—O6 | 1.264 (3) |
C12—N8 | 1.337 (3) | Fe1—N7i | 2.074 (2) |
C12—C13 | 1.389 (4) | Fe1—N5 | 2.088 (2) |
C12—C15 | 1.460 (4) | Fe1—O8 | 2.1102 (18) |
C13—N1 | 1.344 (3) | Fe1—N2 | 2.153 (2) |
C13—C14 | 1.453 (4) | Fe1—O5i | 2.1613 (18) |
C14—O2 | 1.234 (3) | Fe1—N6 | 2.296 (2) |
C14—O1 | 1.267 (3) | Fe2—N1 | 2.071 (2) |
C15—O4 | 1.254 (3) | Fe2—N4 | 2.090 (2) |
C15—O3 | 1.258 (3) | Fe2—N8ii | 2.107 (2) |
C16—N5 | 1.338 (4) | Fe2—O3ii | 2.162 (2) |
C16—C17 | 1.368 (4) | Fe2—O2 | 2.210 (2) |
C16—C21 | 1.509 (4) | Fe2—N3 | 2.215 (2) |
C17—C18 | 1.399 (5) | N7—Fe1iii | 2.074 (2) |
C17—H17 | 0.930 | N8—Fe2iv | 2.107 (2) |
C18—C19 | 1.375 (5) | O1—H1 | 0.820 |
C18—H18 | 0.930 | O3—Fe2iv | 2.162 (2) |
C19—C20 | 1.354 (4) | O5—Fe1iii | 2.1613 (18) |
C19—H19 | 0.930 | O6—H6 | 0.82 (3) |
N4—C1—C2 | 119.5 (3) | O7—C26—O8 | 124.4 (2) |
N4—C1—C6 | 117.7 (2) | O7—C26—C27 | 116.5 (2) |
C2—C1—C6 | 122.8 (2) | O8—C26—C27 | 119.1 (2) |
C1—C2—C3 | 119.5 (3) | N2—C27—C28 | 108.6 (2) |
C1—C2—H2 | 120.3 | N2—C27—C26 | 118.5 (2) |
C3—C2—H2 | 120.3 | C28—C27—C26 | 132.7 (2) |
C4—C3—C2 | 120.7 (3) | N7—C28—C27 | 109.3 (2) |
C4—C3—H3 | 119.7 | N7—C28—C30 | 118.0 (2) |
C2—C3—H3 | 119.7 | C27—C28—C30 | 132.2 (2) |
C5—C4—C3 | 116.8 (3) | N7—C29—N2 | 115.2 (2) |
C5—C4—H4 | 121.6 | N7—C29—H29 | 122.4 |
C3—C4—H4 | 121.6 | N2—C29—H29 | 122.4 |
N4—C5—C4 | 123.1 (3) | O5—C30—O6 | 123.5 (2) |
N4—C5—H5 | 118.5 | O5—C30—C28 | 119.6 (2) |
C4—C5—H5 | 118.5 | O6—C30—C28 | 116.8 (2) |
N3—C6—C7 | 119.7 (3) | N7i—Fe1—N5 | 161.40 (9) |
N3—C6—C1 | 116.0 (2) | N7i—Fe1—O8 | 95.75 (8) |
C7—C6—C1 | 124.3 (2) | N5—Fe1—O8 | 89.80 (8) |
C6—C7—C8 | 120.8 (3) | N7i—Fe1—N2 | 101.96 (8) |
C6—C7—H7 | 119.6 | N5—Fe1—N2 | 96.50 (9) |
C8—C7—H7 | 119.6 | O8—Fe1—N2 | 79.36 (8) |
C9—C8—C7 | 119.4 (3) | N7i—Fe1—O5i | 79.05 (7) |
C9—C8—H8 | 120.3 | N5—Fe1—O5i | 96.88 (8) |
C7—C8—H8 | 120.3 | O8—Fe1—O5i | 172.39 (7) |
C8—C9—C10 | 116.6 (3) | N2—Fe1—O5i | 96.18 (7) |
C8—C9—H9 | 121.7 | N7i—Fe1—N6 | 85.24 (8) |
C10—C9—H9 | 121.7 | N5—Fe1—N6 | 76.21 (9) |
N3—C10—C9 | 124.7 (3) | O8—Fe1—N6 | 103.04 (8) |
N3—C10—H10 | 117.6 | N2—Fe1—N6 | 172.23 (8) |
C9—C10—H10 | 117.6 | O5i—Fe1—N6 | 82.20 (8) |
N1—C11—N8 | 115.3 (2) | N1—Fe2—N4 | 158.38 (9) |
N1—C11—H11 | 122.4 | N1—Fe2—N8ii | 102.12 (8) |
N8—C11—H11 | 122.4 | N4—Fe2—N8ii | 94.04 (9) |
N8—C12—C13 | 108.9 (2) | N1—Fe2—O3ii | 101.41 (8) |
N8—C12—C15 | 118.1 (2) | N4—Fe2—O3ii | 95.76 (8) |
C13—C12—C15 | 132.9 (2) | N8ii—Fe2—O3ii | 78.51 (8) |
N1—C13—C12 | 108.7 (2) | N1—Fe2—O2 | 78.24 (8) |
N1—C13—C14 | 118.4 (2) | N4—Fe2—O2 | 86.62 (8) |
C12—C13—C14 | 132.8 (2) | N8ii—Fe2—O2 | 93.45 (8) |
O2—C14—O1 | 123.5 (3) | O3ii—Fe2—O2 | 171.74 (7) |
O2—C14—C13 | 119.5 (2) | N1—Fe2—N3 | 87.68 (8) |
O1—C14—C13 | 116.9 (2) | N4—Fe2—N3 | 78.15 (9) |
O4—C15—O3 | 124.4 (2) | N8ii—Fe2—N3 | 168.44 (8) |
O4—C15—C12 | 116.6 (2) | O3ii—Fe2—N3 | 93.66 (8) |
O3—C15—C12 | 119.0 (2) | O2—Fe2—N3 | 94.57 (8) |
N5—C16—C17 | 118.8 (3) | C11—N1—C13 | 103.5 (2) |
N5—C16—C21 | 118.7 (2) | C11—N1—Fe2 | 142.88 (18) |
C17—C16—C21 | 122.4 (3) | C13—N1—Fe2 | 112.30 (17) |
C16—C17—C18 | 119.3 (3) | C27—N2—C29 | 103.7 (2) |
C16—C17—H17 | 120.3 | C27—N2—Fe1 | 108.53 (17) |
C18—C17—H17 | 120.3 | C29—N2—Fe1 | 144.53 (17) |
C19—C18—C17 | 121.5 (3) | C6—N3—C10 | 118.8 (2) |
C19—C18—H18 | 119.2 | C6—N3—Fe2 | 112.81 (18) |
C17—C18—H18 | 119.2 | C10—N3—Fe2 | 128.37 (18) |
C20—C19—C18 | 116.1 (3) | C1—N4—C5 | 120.5 (2) |
C20—C19—H19 | 122.0 | C1—N4—Fe2 | 115.04 (18) |
C18—C19—H19 | 122.0 | C5—N4—Fe2 | 124.28 (18) |
C19—C20—N5 | 122.9 (3) | C16—N5—C20 | 121.3 (2) |
C19—C20—H20 | 118.5 | C16—N5—Fe1 | 116.59 (19) |
N5—C20—H20 | 118.5 | C20—N5—Fe1 | 122.02 (18) |
N6—C21—C22 | 119.8 (3) | C21—N6—C25 | 118.1 (2) |
N6—C21—C16 | 115.0 (2) | C21—N6—Fe1 | 112.18 (19) |
C22—C21—C16 | 125.1 (3) | C25—N6—Fe1 | 129.06 (19) |
C21—C22—C23 | 121.4 (3) | C29—N7—C28 | 103.2 (2) |
C21—C22—H22 | 119.3 | C29—N7—Fe1iii | 141.96 (18) |
C23—C22—H22 | 119.3 | C28—N7—Fe1iii | 110.65 (16) |
C24—C23—C22 | 119.3 (3) | C11—N8—C12 | 103.6 (2) |
C24—C23—H23 | 120.3 | C11—N8—Fe2iv | 143.60 (18) |
C22—C23—H23 | 120.3 | C12—N8—Fe2iv | 111.23 (17) |
C23—C24—C25 | 116.6 (3) | C14—O1—H1 | 109.5 |
C23—C24—H24 | 121.7 | C14—O2—Fe2 | 111.30 (17) |
C25—C24—H24 | 121.7 | C15—O3—Fe2iv | 111.86 (16) |
N6—C25—C24 | 124.8 (3) | C30—O5—Fe1iii | 110.75 (15) |
N6—C25—H25 | 117.6 | C30—O6—H6 | 110 (3) |
C24—C25—H25 | 117.6 | C26—O8—Fe1 | 112.45 (16) |
Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) −x+1, y−1/2, −z+1/2; (iii) −x, y+1/2, −z+3/2; (iv) −x+1, y+1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O4 | 0.82 | 1.69 | 2.493 (3) | 167 |
O6—H6···O7 | 0.82 (3) | 1.69 (2) | 2.489 (2) | 167 (2) |
Experimental details
Crystal data | |
Chemical formula | [Fe(C5H2N2O4)(C10H8N2)] |
Mr | 366.12 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 19.9862 (10), 9.8828 (5), 14.4351 (7) |
β (°) | 101.806 (1) |
V (Å3) | 2790.9 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.11 |
Crystal size (mm) | 0.43 × 0.35 × 0.28 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.647, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15091, 5866, 4863 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.632 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.100, 1.00 |
No. of reflections | 5866 |
No. of parameters | 437 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.44, −0.49 |
Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O4 | 0.82 | 1.69 | 2.493 (3) | 167 |
O6—H6···O7 | 0.82 (3) | 1.69 (2) | 2.489 (2) | 167 (2) |
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Complexes containing carboxylic acids are of interest to chemists on account of their potential applications, such as catalysis, optics, information storage, medicine, molecular electrochemistry, biochemistry and biological pharmaceutics (Li et al., 1993; Go et al., 2004). Thus far, N-containing aromatic carboxylic acids, for example adipiodone and acetrizoic acid, have been widely used in organic synthesis, as dye intermediates, sensitization materials and functional pigments (An et al., 2000). Pyridine carboxylic acid is also used extensively in coordination chemistry due to its strong coordinating ability and versatile coordination modes (Baroni et al. (1996); Hundal et al. (2002)).
In the title compound, the asymetric unit contains two crystallographically independent monomer units. As shown in Fig. 1, FeII atoms have a distorted octahedral geometry formed by two carboxylate O atoms and four N atoms, two of which belong to the 2,2'-bipyridine ligand and the other two to the imidazole ring. The Fe—O and Fe—N bond lengths are in the range 2.110 (2)–2.216 (2) and 2.071 (2)–2.296 (2) Å, respectively. The carboxy and carboxylate groups of the 5-carboxy-4-carboxylatoimidazol-1-ide ligand coordinate in a monodentate fashion to two FeII atoms, giving rise to one-dimensional zigzag chains along [010] (Fig. 2). The 2,2'-bipyridine ligands are situated between these chains.