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The title compound, (C10H9N2)[Fe(C7H3NO4)2]·3H2O, was prepared from the ligand pyridine-2,6-dicarboxylic acid with FeCl3·6H2O in the presence of 2,2-bipyridine. The FeIII atom is six-coordinate in a distorted octa­hedral geometry. The compound contains protonated 2,2′-bipyridine and doubly deprotonated pyridine-2,6-dicarboxyl­ate (pydc) units; the protonated 2,2′-bipyridine bridges adjacent [Fe(pydc)2] complex units through hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805036469/hg6258sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805036469/hg6258Isup2.hkl
Contains datablock I

CCDC reference: 293908

Key indicators

  • Single-crystal X-ray study
  • T = 289 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.029
  • wR factor = 0.089
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H18 .. H26 .. 2.01 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 14 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Fe1 - N1 .. 5.94 su PLAT432_ALERT_2_C Short Inter X...Y Contact O7 .. C19 .. 3.00 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C14 H6 Fe N2 O8 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C10 H9 N2 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H2 O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4 H2 O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 5 H2 O
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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: SHELXTL.

2-(2-Pyridyl)pyridinium bis(pyridine-2,6-dicarboxylato-κ2O2,O6)iron(III) trihydrate top
Crystal data top
(C10H9N2)[Fe(C7H3NO4)2]·3H2OZ = 2
Mr = 597.30F(000) = 614
Triclinic, P1Dx = 1.563 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.4528 (19) ÅCell parameters from 1694 reflections
b = 10.840 (2) Åθ = 2.2–28.2°
c = 13.178 (3) ŵ = 0.66 mm1
α = 104.62 (3)°T = 289 K
β = 99.57 (3)°Block, green
γ = 97.02 (3)°0.19 × 0.16 × 0.14 mm
V = 1269.3 (4) Å3
Data collection top
Bruker SMART CCD
diffractometer
6109 independent reflections
Radiation source: fine-focus sealed tube5427 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
φ and ω scansθmax = 28.2°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 1212
Tmin = 0.884, Tmax = 0.913k = 1414
15248 measured reflectionsl = 1717
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029All H-atom parameters refined
wR(F2) = 0.089 w = 1/[σ2(Fo2) + (0.0557P)2 + 0.1599P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.003
6109 reflectionsΔρmax = 0.30 e Å3
446 parametersΔρmin = 0.29 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.042 (2)
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
Fe11.21159 (2)1.012510 (17)0.276042 (13)0.03895 (8)
C11.10970 (14)0.89091 (13)0.04497 (10)0.0404 (3)
C21.10646 (18)0.86523 (16)0.06389 (11)0.0512 (3)
H131.025 (2)0.8003 (17)0.1145 (15)0.055 (5)*
C31.2132 (2)0.93735 (18)0.09575 (13)0.0579 (4)
H161.214 (2)0.9295 (19)0.1634 (16)0.061 (5)*
C41.31930 (19)1.03177 (17)0.02112 (13)0.0540 (4)
H151.392 (2)1.0823 (18)0.0411 (15)0.059 (5)*
C51.31569 (15)1.05072 (13)0.08602 (11)0.0430 (3)
C61.00540 (15)0.82893 (13)0.10014 (11)0.0437 (3)
C71.41809 (16)1.14479 (14)0.18294 (13)0.0496 (3)
C81.28169 (13)0.96779 (12)0.48805 (11)0.0381 (3)
C91.28659 (17)0.98559 (16)0.59655 (12)0.0492 (3)
H91.345 (2)0.946 (2)0.6310 (17)0.069 (6)*
C101.20997 (19)1.07602 (16)0.64695 (12)0.0533 (4)
H231.214 (2)1.088 (2)0.7161 (19)0.075 (6)*
C111.13078 (16)1.14499 (14)0.58981 (12)0.0476 (3)
H31.077 (2)1.2127 (19)0.6215 (16)0.062 (5)*
C121.13216 (13)1.12264 (11)0.48240 (10)0.0364 (2)
C131.35535 (15)0.87677 (13)0.41572 (12)0.0450 (3)
C141.05822 (14)1.18649 (12)0.40357 (12)0.0418 (3)
C150.74181 (14)1.51557 (12)0.55089 (12)0.0413 (3)
C160.65395 (14)1.59761 (13)0.51764 (14)0.0469 (3)
H140.6135 (19)1.6575 (17)0.5703 (14)0.056 (5)*
C170.63148 (16)1.60073 (14)0.41259 (15)0.0517 (3)
H120.572 (2)1.6543 (19)0.3915 (16)0.064 (5)*
C180.69487 (19)1.52254 (16)0.33987 (15)0.0574 (4)
H20.682 (2)1.5261 (19)0.2675 (17)0.072 (6)*
C190.78036 (19)1.44211 (16)0.37424 (14)0.0549 (4)
H110.826 (2)1.384 (2)0.3259 (18)0.076 (6)*
C200.9213 (3)1.4181 (2)0.77323 (17)0.0728 (5)
H81.003 (3)1.375 (2)0.7816 (19)0.082 (7)*
C210.8512 (3)1.4641 (2)0.85575 (17)0.0788 (6)
H220.885 (2)1.453 (2)0.928 (2)0.084 (7)*
C220.7418 (3)1.5316 (2)0.83785 (16)0.0756 (6)
H10.696 (3)1.567 (3)0.892 (2)0.101 (8)*
C230.7039 (2)1.55318 (17)0.73884 (14)0.0598 (4)
H70.629 (2)1.6003 (19)0.7242 (16)0.063 (5)*
C240.77842 (15)1.50220 (13)0.65973 (12)0.0463 (3)
O10.90329 (13)0.74476 (12)0.04758 (10)0.0654 (3)
O21.03544 (11)0.87399 (10)0.20259 (8)0.0475 (2)
O31.52052 (15)1.21704 (13)0.17306 (12)0.0750 (4)
O41.38381 (12)1.13941 (10)0.27249 (9)0.0535 (3)
O51.42644 (15)0.80468 (13)0.45041 (12)0.0715 (4)
O61.33437 (12)0.88697 (10)0.31892 (8)0.0503 (2)
O70.98110 (13)1.26553 (11)0.43196 (11)0.0626 (3)
O81.08591 (12)1.14980 (10)0.30978 (8)0.0486 (2)
O91.3130 (2)1.38080 (18)0.87714 (16)0.0854 (5)
H171.252 (2)1.346 (2)0.8957 (19)0.076 (7)*
O100.6738 (2)1.35037 (19)1.04958 (16)0.0976 (5)
H180.584 (2)1.3777 (19)1.0375 (15)0.055 (5)*
H60.608 (3)1.308 (3)1.087 (2)0.120 (10)*
O110.5145 (2)1.2095 (2)0.84814 (18)0.0889 (5)
H40.550 (3)1.198 (3)0.797 (2)0.101 (9)*
H260.578 (3)1.248 (3)0.897 (2)0.096 (10)*
N11.21225 (12)0.98084 (10)0.11519 (9)0.0384 (2)
N21.20706 (10)1.03623 (9)0.43515 (8)0.0334 (2)
N30.80041 (13)1.44057 (11)0.47627 (11)0.0454 (3)
H100.854 (2)1.3940 (19)0.4920 (16)0.060 (5)*
N40.88636 (16)1.43551 (14)0.67615 (12)0.0586 (3)
H51.377 (3)1.347 (4)0.882 (3)0.151 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.04496 (12)0.04056 (12)0.03181 (11)0.01044 (8)0.01206 (7)0.00678 (7)
C10.0443 (6)0.0415 (6)0.0366 (6)0.0158 (5)0.0089 (5)0.0090 (5)
C20.0610 (9)0.0570 (8)0.0357 (7)0.0207 (7)0.0070 (6)0.0101 (6)
C30.0769 (11)0.0711 (10)0.0370 (7)0.0290 (8)0.0207 (7)0.0217 (7)
C40.0637 (9)0.0620 (9)0.0533 (8)0.0234 (7)0.0284 (7)0.0297 (7)
C50.0469 (7)0.0434 (7)0.0468 (7)0.0160 (5)0.0183 (6)0.0178 (5)
C60.0446 (7)0.0413 (7)0.0435 (7)0.0101 (5)0.0102 (5)0.0065 (5)
C70.0493 (7)0.0441 (7)0.0586 (9)0.0092 (6)0.0198 (6)0.0136 (6)
C80.0348 (6)0.0384 (6)0.0409 (6)0.0055 (5)0.0074 (5)0.0111 (5)
C90.0501 (8)0.0555 (8)0.0418 (7)0.0026 (6)0.0050 (6)0.0193 (6)
C100.0644 (9)0.0568 (9)0.0354 (7)0.0029 (7)0.0177 (6)0.0082 (6)
C110.0525 (7)0.0412 (7)0.0459 (7)0.0015 (6)0.0246 (6)0.0005 (6)
C120.0348 (6)0.0299 (5)0.0419 (6)0.0026 (4)0.0143 (5)0.0025 (4)
C130.0403 (6)0.0432 (7)0.0527 (8)0.0148 (5)0.0099 (5)0.0117 (6)
C140.0365 (6)0.0317 (6)0.0554 (8)0.0072 (5)0.0119 (5)0.0068 (5)
C150.0364 (6)0.0305 (6)0.0547 (8)0.0049 (4)0.0117 (5)0.0068 (5)
C160.0362 (6)0.0328 (6)0.0686 (9)0.0072 (5)0.0124 (6)0.0072 (6)
C170.0421 (7)0.0388 (7)0.0745 (10)0.0105 (5)0.0055 (7)0.0190 (7)
C180.0619 (9)0.0565 (9)0.0573 (9)0.0155 (7)0.0095 (7)0.0212 (7)
C190.0620 (9)0.0513 (8)0.0566 (9)0.0221 (7)0.0191 (7)0.0138 (7)
C200.0851 (13)0.0709 (12)0.0658 (11)0.0239 (10)0.0075 (10)0.0253 (9)
C210.0987 (16)0.0786 (13)0.0502 (10)0.0061 (11)0.0048 (10)0.0131 (9)
C220.0822 (13)0.0797 (13)0.0504 (10)0.0032 (10)0.0161 (9)0.0044 (9)
C230.0572 (9)0.0567 (9)0.0541 (9)0.0070 (7)0.0110 (7)0.0036 (7)
C240.0446 (7)0.0351 (6)0.0544 (8)0.0036 (5)0.0097 (6)0.0056 (5)
O10.0577 (7)0.0642 (7)0.0583 (7)0.0097 (5)0.0077 (5)0.0005 (5)
O20.0507 (5)0.0487 (5)0.0410 (5)0.0023 (4)0.0155 (4)0.0081 (4)
O30.0697 (8)0.0649 (8)0.0869 (9)0.0101 (6)0.0324 (7)0.0145 (7)
O40.0559 (6)0.0516 (6)0.0465 (6)0.0009 (4)0.0127 (4)0.0051 (4)
O50.0728 (8)0.0719 (8)0.0810 (9)0.0435 (7)0.0136 (7)0.0277 (7)
O60.0566 (6)0.0514 (6)0.0475 (6)0.0258 (5)0.0204 (4)0.0082 (4)
O70.0580 (6)0.0493 (6)0.0875 (9)0.0291 (5)0.0257 (6)0.0152 (6)
O80.0558 (6)0.0469 (5)0.0458 (5)0.0208 (4)0.0081 (4)0.0136 (4)
O90.0870 (11)0.0851 (11)0.1068 (13)0.0221 (9)0.0397 (10)0.0510 (10)
O100.1171 (15)0.0899 (12)0.0986 (13)0.0178 (11)0.0396 (11)0.0382 (10)
O110.0848 (11)0.1100 (13)0.0770 (11)0.0231 (10)0.0431 (10)0.0152 (10)
N10.0424 (5)0.0404 (5)0.0356 (5)0.0120 (4)0.0126 (4)0.0111 (4)
N20.0328 (5)0.0332 (5)0.0337 (5)0.0070 (4)0.0097 (4)0.0059 (4)
N30.0464 (6)0.0385 (6)0.0556 (7)0.0182 (5)0.0140 (5)0.0136 (5)
N40.0653 (8)0.0557 (7)0.0601 (8)0.0210 (6)0.0141 (6)0.0195 (6)
Geometric parameters (Å, º) top
Fe1—O42.0139 (12)C13—O61.2928 (19)
Fe1—O62.0185 (11)C14—O71.2194 (17)
Fe1—O22.0209 (13)C14—O71.2194 (17)
Fe1—O82.0243 (12)C14—O81.2803 (18)
Fe1—N22.0553 (11)C15—N31.3499 (18)
Fe1—N12.0612 (12)C15—C161.389 (2)
C1—N11.3274 (18)C15—C241.466 (2)
C1—C21.3849 (19)C16—C171.375 (2)
C1—C61.508 (2)C16—H140.985 (19)
C2—C31.385 (2)C17—C181.379 (3)
C2—H130.996 (18)C17—H120.92 (2)
C3—C41.391 (3)C18—C191.367 (2)
C3—H160.88 (2)C18—H20.95 (2)
C4—C51.381 (2)C19—N31.331 (2)
C4—H150.939 (19)C19—H110.97 (2)
C5—N11.3299 (17)C20—N41.334 (2)
C5—C71.516 (2)C20—C211.385 (3)
C6—O11.2196 (18)C20—H80.96 (2)
C6—O21.2837 (17)C21—C221.361 (4)
C7—O31.2148 (19)C21—H221.00 (2)
C7—O41.2877 (19)C22—C231.380 (3)
C8—N21.3265 (17)C22—H10.92 (3)
C8—C91.386 (2)C23—C241.392 (2)
C8—C131.5101 (19)C23—H70.95 (2)
C9—C101.390 (2)C24—N41.340 (2)
C9—H90.88 (2)O9—H170.757 (19)
C10—C111.386 (3)O9—H50.749 (19)
C10—H230.88 (2)O10—H180.93 (2)
C11—C121.3770 (19)O10—H60.99 (3)
C11—H30.99 (2)O11—H40.79 (3)
C12—N21.3344 (16)O11—H260.79 (3)
C12—C141.512 (2)N3—H100.80 (2)
C13—O51.2156 (18)
O4—Fe1—O694.09 (5)O6—C13—C8112.92 (11)
O4—Fe1—O2151.76 (4)O7—C14—O8126.02 (14)
O6—Fe1—O293.87 (5)O7—C14—O8126.02 (14)
O4—Fe1—O893.80 (5)O7—C14—C12120.14 (14)
O6—Fe1—O8151.63 (4)O7—C14—C12120.14 (14)
O2—Fe1—O891.94 (5)O8—C14—C12113.85 (11)
O4—Fe1—N2106.14 (5)N3—C15—C16117.28 (14)
O6—Fe1—N275.70 (5)N3—C15—C24116.20 (12)
O2—Fe1—N2102.08 (5)C16—C15—C24126.52 (13)
O8—Fe1—N275.93 (5)C17—C16—C15119.75 (14)
O4—Fe1—N175.92 (6)C17—C16—H14120.2 (10)
O6—Fe1—N1103.12 (5)C15—C16—H14119.9 (11)
O2—Fe1—N175.89 (5)C16—C17—C18120.51 (14)
O8—Fe1—N1105.23 (5)C16—C17—H12118.7 (13)
N2—Fe1—N1177.64 (4)C18—C17—H12120.8 (13)
N1—C1—C2120.69 (14)C19—C18—C17118.75 (16)
N1—C1—C6111.34 (11)C19—C18—H2120.2 (13)
C2—C1—C6127.97 (14)C17—C18—H2121.0 (13)
C1—C2—C3117.40 (15)N3—C19—C18119.70 (15)
C1—C2—H13118.6 (11)N3—C19—H11118.6 (13)
C3—C2—H13124.0 (10)C18—C19—H11121.7 (13)
C2—C3—C4121.16 (14)N4—C20—C21123.3 (2)
C2—C3—H16122.0 (13)N4—C20—H8113.4 (14)
C4—C3—H16116.7 (13)C21—C20—H8123.2 (14)
C5—C4—C3117.88 (15)C22—C21—C20118.8 (2)
C5—C4—H15119.6 (12)C22—C21—H22121.0 (14)
C3—C4—H15122.5 (11)C20—C21—H22120.1 (14)
N1—C5—C4120.17 (14)C21—C22—C23119.6 (2)
N1—C5—C7111.10 (12)C21—C22—H1121.0 (17)
C4—C5—C7128.73 (14)C23—C22—H1119.3 (17)
O1—C6—O2126.00 (14)C22—C23—C24118.11 (19)
O1—C6—C1120.19 (13)C22—C23—H7121.5 (13)
O2—C6—C1113.81 (12)C24—C23—H7120.4 (12)
O3—C7—O4125.44 (16)N4—C24—C23122.98 (16)
O3—C7—C5121.16 (15)N4—C24—C15115.00 (14)
O4—C7—C5113.40 (12)C23—C24—C15122.00 (15)
N2—C8—C9120.56 (13)C6—O2—Fe1120.37 (9)
N2—C8—C13111.47 (11)C7—O4—Fe1120.83 (10)
C9—C8—C13127.96 (13)C13—O6—Fe1120.88 (9)
C8—C9—C10117.78 (15)C14—O8—Fe1120.42 (9)
C8—C9—H9118.5 (14)H17—O9—H5109 (3)
C10—C9—H9123.4 (14)H18—O10—H671.7 (19)
C11—C10—C9120.72 (14)H4—O11—H26106 (3)
C11—C10—H23121.6 (15)C1—N1—C5122.70 (12)
C9—C10—H23117.7 (15)C1—N1—Fe1118.56 (9)
C12—C11—C10118.08 (13)C5—N1—Fe1118.74 (10)
C12—C11—H3117.3 (11)C8—N2—C12122.25 (11)
C10—C11—H3124.6 (11)C8—N2—Fe1118.98 (8)
N2—C12—C11120.60 (13)C12—N2—Fe1118.75 (9)
N2—C12—C14111.00 (11)C19—N3—C15124.00 (13)
C11—C12—C14128.39 (12)C19—N3—H10114.9 (15)
O5—C13—O6126.63 (14)C15—N3—H10121.0 (15)
O5—C13—C8120.45 (14)C20—N4—C24117.24 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H15···O11i0.939 (19)2.56 (2)3.457 (3)159.4 (15)
O10—H6···O3ii0.99 (3)1.91 (3)2.880 (2)167 (3)
C17—H12···O5iii0.92 (2)2.32 (2)3.115 (2)144.0 (17)
N3—H10···O70.80 (2)2.04 (2)2.7246 (17)143.3 (19)
O9—H5···O11iv0.75 (2)2.11 (2)2.823 (3)161 (4)
Symmetry codes: (i) x+1, y, z1; (ii) x1, y, z+1; (iii) x1, y+1, z; (iv) x+1, y, z.
 

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