Tris(2-N-methyl­amino­carbonyl-3-hydr­oxy-1,6-dimethyl-1,4-dihydro-4-pyridinonato)­iron(III) dimethyl­formamide disolvate

Tam, T.F.; Leung-Toung, R.; Wang, Y.; Spino, M.; Williams, G.; Lough, A.J.

doi:10.1107/S1600536805029776

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Tris(2-N-methylaminocarbonyl-3-hydroxy-1,6-dimethyl-1,4-dihydro-4-pyridinonato)iron(III) dimethylformamide disolvate

T. F. Tam, R. Leung-Toung, Y. Wang, M. Spino, G. Williams and A. J. Lough

In the crystal structure of the title compound, Fe(C₉H₁₁N₂O₃)₃·2C₃H₇NO, the Fe^III ion is six-coordinate with a distorted octahedral configuration consisting of six donor O atoms from three bidentate ligands. Two of the amide NH groups are involved in intramolecular N—H

O_p (p = phenolic) hydrogen bonds, while the third is involved in forming centrosymmetric dimers via intermolecular N—H

O_p hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029776/hb6268sup1.cif Contains datablocks k02141, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029776/hb6268Isup2.hkl Contains datablock I

CCDC reference: 287568

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.003 Å
R factor = 0.047
wR factor = 0.126
Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.59 Ratio
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N7
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N8
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C32

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Iron chelation therapy is now a mainstay for the treatment of human conditions of iron overload, e.g. transfusion-dependent β-thalassaemia (Cohen et al., 2004). At present, the bidentate 1,2-dimethyl-3-hydroxy-4-pyridinone ligand (L1; also known as CP20, deferiprone or Ferriprox) is the only oral iron chelator drug approved (in 48 countries) for β-thalassaemic patients (Tam et al., 2003). However, L1 undergoes extensive metabolism in the liver, and more than 85% of the administered drug is recovered in the urine as the inactive 3-O-glucuronide. Hence, information on the structure of the ligand (L), as well as of the FeL₃ chelate, is important for the design of new bidentate Fe^III-sequestering agents with better pharmacokinetic profiles. The single-crystal X-ray structures of Fe(L1)₃ (Charalambous et al., 1988; Clarke et al., 1992) and M(L1)₃ (M = Al and Ga; Nelson et al., 1988) have been reported previously. We report here the structure of the title compound, (I), an iron(III) complex of a related ligand, 2-N-methylaminocarbonyl-3-hydroxy-1,6-dimethyl-1,4-dihydro-4-pyridinone (L2).

The structure of (I) is shown in Fig. 1, and selected geometrical data are given in Table 1. The Fe^III ion is six-coordinate, with a distorted octahedral configuration consisting of six donor O atoms from three bidentate ligands. There is a difference in the Fe—O bond lengths (Table 1), with three (Fe—O2,O5,O8) being significantly shorter than the other three (Fe—O1,O3,O7). In addition, the short and long bond distances (Table 1) for the chelating C—O groups indicate that some ketonic character has been retained in the complex.

The amide groups of all three ligands are rotated out of the planes of the respective pyridinone rings to which they are bonded, giving dihedral angles of −102.5 (3), −135.3 (3) and 146.6 (3)° for C2—C3—C6—O3, C11—C12—C15—O6 and C20—C21—C24—O9, respectively. The largest out of plane rotation for the amide group containing N2 facilitates the formation of an intermolecular N—H···O hydrogen bond linking molecules into centrosymmetric dimers (Fig. 2), creating R²₂(24) rings (Bernstein et al., 1995), while the NH groups of the other two amide moieties are involved in intramolecular N—H···O hydrogen bonds, one of which is also involved in the formation of an N—H···O hydrogen bond to one dimethylformamide solvent molecule (see Table 2 for hydrogen-bond geometries). There are also numerous weak C—H···O interactions present in the crystal structure of (I), with H···O distances ranging from 2.17 to 2.59 Å, but these are not discussed in detail here.

Experimental top

The ligand (2.15 g, 11.0 mmol) (Tam & Li, 2002) was dissolved in a NaHCO₃/Na₂CO₃ buffer solution (100 ml, pH 9.7), and FeCl₃·6H₂O (0.988 g, 3.67 mmol) was added. The mixture was stirred at room temperature for a few days. The resulting red solid was collected by filtration, and was recrystallized from a mixture of CH₂Cl₂ and ethyl acetate. Suitable crystals of (I) for X-ray structure determination were obtained by recrystallization from wet DMF and diethyl ether.

Computing details top

Data collection: Collect (Nonius, 2003); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. View of (I), showing 30% probability displacement ellipsoids (arbitrary spheres for the H atoms involved in hydrogen bonds; other H atoms have been omitted). Dashed lines lines indicate the hydrogen bonds.
	Fig. 2. View of an N—H···O hydrogen-bonded (dashed lines) centrosymmetric dimer of Fe(L2)₃ molecules in (I). Colour codes: green Fe, red O, blue N and black C. H atoms not involved in hydrogen bonding have been omitted.

(I) top

Crystal data top

Fe(C₉H₁₁N₂O₃)₃·2C₃H₇NO	Z = 2
M_r = 787.64	F(000) = 830
Triclinic, P1	D_x = 1.435 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.1137 (2) Å	Cell parameters from 24188 reflections
b = 13.0414 (3) Å	θ = 2.9–27.5°
c = 13.8382 (3) Å	µ = 0.48 mm⁻¹
α = 79.1515 (10)°	T = 150 K
β = 68.8106 (10)°	Needle, red
γ = 79.7017 (9)°	0.10 × 0.06 × 0.04 mm
V = 1823.18 (7) Å³

Data collection top

Bruker–Nonius KappaCCD diffractometer	8323 independent reflections
Radiation source: fine-focus sealed tube	6063 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 2.9°
ϕ scans and ω scans with κ offsets	h = −14→14
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −16→16
T_min = 0.910, T_max = 0.982	l = −17→17
24188 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0484P)² + 0.7105P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
8323 reflections	Δρ_max = 0.55 e Å⁻³
492 parameters	Δρ_min = −0.49 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0071 (13)

Crystal data top

Fe(C₉H₁₁N₂O₃)₃·2C₃H₇NO	γ = 79.7017 (9)°
M_r = 787.64	V = 1823.18 (7) Å³
Triclinic, P1	Z = 2
a = 11.1137 (2) Å	Mo Kα radiation
b = 13.0414 (3) Å	µ = 0.48 mm⁻¹
c = 13.8382 (3) Å	T = 150 K
α = 79.1515 (10)°	0.10 × 0.06 × 0.04 mm
β = 68.8106 (10)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	8323 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	6063 reflections with I > 2σ(I)
T_min = 0.910, T_max = 0.982	R_int = 0.062
24188 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.01	Δρ_max = 0.55 e Å⁻³
8323 reflections	Δρ_min = −0.49 e Å⁻³
492 parameters

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

	x	y	z	U_iso*/U_eq
Fe1	0.28889 (3)	0.78711 (3)	0.31899 (3)	0.02347 (11)
O1	0.13327 (15)	0.86403 (13)	0.42099 (12)	0.0277 (4)
O2	0.15914 (15)	0.78742 (12)	0.25152 (12)	0.0249 (3)
O3	−0.0445 (2)	0.88024 (15)	0.09043 (14)	0.0442 (5)
O4	0.39554 (15)	0.78024 (12)	0.41420 (12)	0.0273 (4)
O5	0.26770 (16)	0.64055 (12)	0.39429 (12)	0.0272 (4)
O6	0.12059 (19)	0.42974 (16)	0.64768 (15)	0.0457 (5)
O7	0.44153 (15)	0.74585 (12)	0.19147 (13)	0.0282 (4)
O8	0.34766 (15)	0.92895 (12)	0.25283 (13)	0.0277 (4)
O9	0.5792 (2)	1.15986 (18)	0.1839 (2)	0.0608 (6)
N1	−0.18036 (19)	0.89789 (16)	0.32609 (16)	0.0293 (4)
N2	−0.0428 (2)	0.71133 (16)	0.16850 (16)	0.0329 (5)
H2A	−0.0475	0.6693	0.2272	0.040*
N3	0.34979 (18)	0.51250 (15)	0.62407 (15)	0.0276 (4)
N4	0.18348 (19)	0.43692 (16)	0.47298 (16)	0.0306 (4)
H4A	0.2386	0.4583	0.4114	0.037*
N5	0.64957 (19)	0.99485 (17)	0.04944 (16)	0.0322 (5)
N6	0.3728 (2)	1.12730 (18)	0.2389 (2)	0.0465 (6)
H6A	0.3171	1.0888	0.2359	0.056*
C1	0.0307 (2)	0.87723 (17)	0.39419 (17)	0.0240 (5)
C2	0.0437 (2)	0.83489 (17)	0.30184 (17)	0.0228 (5)
C3	−0.0623 (2)	0.84712 (18)	0.26940 (18)	0.0261 (5)
C4	−0.1943 (2)	0.93950 (19)	0.4134 (2)	0.0314 (5)
C5	−0.0893 (2)	0.92964 (19)	0.4468 (2)	0.0296 (5)
H5A	−0.0993	0.9594	0.5073	0.036*
C6	−0.0494 (2)	0.81407 (19)	0.16729 (19)	0.0292 (5)
C7	−0.0279 (3)	0.6658 (2)	0.0762 (2)	0.0475 (7)
H7A	−0.0269	0.5893	0.0938	0.071*
H7B	0.0539	0.6822	0.0211	0.071*
H7C	−0.1008	0.6952	0.0514	0.071*
C8	−0.2936 (2)	0.9061 (2)	0.2919 (2)	0.0412 (7)
H8A	−0.3672	0.8802	0.3509	0.062*
H8B	−0.2715	0.8637	0.2350	0.062*
H8C	−0.3173	0.9798	0.2672	0.062*
C9	−0.3236 (3)	0.9950 (2)	0.4713 (2)	0.0443 (7)
H9A	−0.3149	1.0291	0.5254	0.066*
H9B	−0.3865	0.9440	0.5041	0.066*
H9C	−0.3540	1.0483	0.4223	0.066*
C10	0.3841 (2)	0.69697 (18)	0.48249 (18)	0.0248 (5)
C11	0.3128 (2)	0.61858 (18)	0.47260 (17)	0.0245 (5)
C12	0.2925 (2)	0.53021 (19)	0.54708 (18)	0.0260 (5)
C13	0.4169 (2)	0.5842 (2)	0.63377 (19)	0.0317 (5)
C14	0.4330 (2)	0.6767 (2)	0.56441 (19)	0.0309 (5)
H14A	0.4785	0.7275	0.5731	0.037*
C15	0.1930 (2)	0.46036 (18)	0.55926 (19)	0.0288 (5)
C16	0.0819 (3)	0.3759 (2)	0.4802 (2)	0.0383 (6)
H16A	0.0584	0.3953	0.4168	0.058*
H16B	0.0053	0.3906	0.5414	0.058*
H16C	0.1139	0.3007	0.4872	0.058*
C17	0.3462 (3)	0.4106 (2)	0.6930 (2)	0.0364 (6)
H17A	0.4291	0.3907	0.7057	0.055*
H17B	0.3319	0.3565	0.6592	0.055*
H17C	0.2753	0.4172	0.7597	0.055*
C18	0.4712 (3)	0.5635 (3)	0.7213 (2)	0.0446 (7)
H18A	0.4024	0.5448	0.7876	0.067*
H18B	0.5047	0.6268	0.7248	0.067*
H18C	0.5418	0.5053	0.7087	0.067*
C19	0.5094 (2)	0.82285 (19)	0.14194 (18)	0.0272 (5)
C20	0.4609 (2)	0.92401 (18)	0.17708 (18)	0.0255 (5)
C21	0.5344 (2)	1.00793 (19)	0.13354 (19)	0.0283 (5)
C22	0.6930 (2)	0.9018 (2)	0.01139 (19)	0.0327 (6)
C23	0.6256 (2)	0.8157 (2)	0.05765 (19)	0.0324 (5)
H23A	0.6592	0.7503	0.0314	0.039*
C24	0.4979 (3)	1.1057 (2)	0.1849 (2)	0.0366 (6)
C25	0.3250 (3)	1.2117 (3)	0.3024 (3)	0.0590 (9)
H25A	0.2370	1.2022	0.3510	0.088*
H25B	0.3230	1.2792	0.2573	0.088*
H25C	0.3824	1.2112	0.3421	0.088*
C26	0.7246 (3)	1.0846 (2)	−0.0055 (2)	0.0514 (8)
H26A	0.7450	1.0885	−0.0811	0.077*
H26B	0.8054	1.0745	0.0102	0.077*
H26C	0.6728	1.1501	0.0181	0.077*
C27	0.8154 (3)	0.8938 (3)	−0.0817 (2)	0.0426 (7)
H27A	0.8872	0.9118	−0.0655	0.064*
H27B	0.8031	0.9426	−0.1415	0.064*
H27C	0.8357	0.8218	−0.0990	0.064*
N7	0.0956 (2)	0.73488 (19)	0.75274 (17)	0.0398 (5)
O10	0.1436 (2)	0.58480 (17)	0.85225 (16)	0.0527 (5)
C28	0.0412 (4)	0.7850 (3)	0.6726 (3)	0.0683 (10)
H28A	−0.0033	0.7348	0.6574	0.102*
H28B	0.1111	0.8083	0.6089	0.102*
H28C	−0.0211	0.8459	0.6972	0.102*
C29	0.1687 (3)	0.7974 (3)	0.7827 (3)	0.0538 (8)
H29A	0.1925	0.7583	0.8423	0.081*
H29B	0.1152	0.8635	0.8024	0.081*
H29C	0.2477	0.8125	0.7236	0.081*
C30	0.0919 (3)	0.6329 (2)	0.7895 (2)	0.0436 (7)
H30A	0.0456	0.5947	0.7654	0.052*
O11	0.2237 (3)	0.4605 (2)	0.24787 (19)	0.0664 (7)
N8	0.2922 (3)	0.54095 (19)	0.0819 (2)	0.0525 (7)
C31	0.3368 (5)	0.6347 (3)	0.0119 (3)	0.0888 (15)
H31A	0.3473	0.6850	0.0519	0.133*
H31B	0.2729	0.6667	−0.0220	0.133*
H31C	0.4205	0.6158	−0.0414	0.133*
C32	0.2877 (4)	0.4527 (3)	0.0343 (3)	0.0704 (11)
H32A	0.2566	0.3943	0.0890	0.106*
H32B	0.3750	0.4304	−0.0124	0.106*
H32C	0.2285	0.4735	−0.0059	0.106*
C33	0.2574 (3)	0.5368 (2)	0.1850 (3)	0.0527 (8)
H33A	0.2592	0.5986	0.2112	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.02321 (18)	0.02204 (18)	0.02636 (19)	−0.00289 (12)	−0.01067 (13)	−0.00142 (12)
O1	0.0258 (8)	0.0318 (9)	0.0298 (9)	−0.0028 (7)	−0.0132 (7)	−0.0077 (7)
O2	0.0245 (8)	0.0249 (8)	0.0268 (8)	−0.0007 (6)	−0.0108 (7)	−0.0046 (6)
O3	0.0644 (13)	0.0429 (11)	0.0341 (10)	−0.0199 (10)	−0.0288 (10)	0.0109 (8)
O4	0.0276 (8)	0.0250 (8)	0.0319 (9)	−0.0048 (7)	−0.0139 (7)	−0.0008 (7)
O5	0.0328 (9)	0.0248 (8)	0.0278 (9)	−0.0064 (7)	−0.0156 (7)	0.0007 (6)
O6	0.0476 (11)	0.0570 (13)	0.0323 (10)	−0.0245 (10)	−0.0125 (9)	0.0099 (9)
O7	0.0278 (8)	0.0256 (8)	0.0311 (9)	−0.0036 (7)	−0.0101 (7)	−0.0035 (7)
O8	0.0252 (8)	0.0233 (8)	0.0322 (9)	−0.0023 (6)	−0.0081 (7)	−0.0023 (7)
O9	0.0505 (13)	0.0507 (13)	0.0900 (18)	−0.0192 (11)	−0.0243 (13)	−0.0172 (12)
N1	0.0247 (10)	0.0305 (11)	0.0362 (11)	−0.0022 (8)	−0.0168 (9)	−0.0012 (9)
N2	0.0435 (12)	0.0329 (12)	0.0247 (10)	−0.0087 (10)	−0.0133 (9)	−0.0018 (8)
N3	0.0252 (10)	0.0290 (11)	0.0259 (10)	0.0014 (8)	−0.0101 (8)	0.0012 (8)
N4	0.0314 (11)	0.0299 (11)	0.0309 (11)	−0.0050 (9)	−0.0106 (9)	−0.0040 (8)
N5	0.0270 (10)	0.0390 (12)	0.0314 (11)	−0.0098 (9)	−0.0126 (9)	0.0042 (9)
N6	0.0402 (13)	0.0332 (13)	0.0691 (17)	−0.0049 (10)	−0.0159 (12)	−0.0187 (12)
C1	0.0257 (11)	0.0213 (11)	0.0259 (12)	−0.0051 (9)	−0.0104 (9)	0.0003 (9)
C2	0.0245 (11)	0.0190 (11)	0.0252 (11)	−0.0034 (9)	−0.0103 (9)	0.0011 (8)
C3	0.0289 (12)	0.0238 (12)	0.0280 (12)	−0.0052 (9)	−0.0138 (10)	0.0014 (9)
C4	0.0264 (12)	0.0287 (13)	0.0381 (14)	−0.0001 (10)	−0.0105 (11)	−0.0061 (10)
C5	0.0268 (12)	0.0303 (13)	0.0342 (13)	−0.0027 (10)	−0.0107 (10)	−0.0098 (10)
C6	0.0273 (12)	0.0357 (14)	0.0289 (13)	−0.0098 (10)	−0.0148 (10)	0.0019 (10)
C7	0.064 (2)	0.0491 (18)	0.0336 (15)	−0.0096 (15)	−0.0181 (14)	−0.0107 (13)
C8	0.0309 (13)	0.0507 (17)	0.0517 (17)	−0.0011 (12)	−0.0265 (13)	−0.0088 (13)
C9	0.0275 (13)	0.0487 (17)	0.0561 (18)	0.0044 (12)	−0.0136 (13)	−0.0157 (14)
C10	0.0204 (10)	0.0260 (12)	0.0273 (12)	0.0004 (9)	−0.0080 (9)	−0.0051 (9)
C11	0.0228 (11)	0.0256 (12)	0.0253 (12)	0.0004 (9)	−0.0098 (9)	−0.0035 (9)
C12	0.0244 (11)	0.0302 (12)	0.0237 (12)	−0.0023 (9)	−0.0095 (9)	−0.0027 (9)
C13	0.0237 (12)	0.0434 (15)	0.0273 (13)	−0.0010 (10)	−0.0107 (10)	−0.0023 (10)
C14	0.0282 (12)	0.0381 (14)	0.0311 (13)	−0.0059 (10)	−0.0150 (10)	−0.0039 (10)
C15	0.0331 (13)	0.0230 (12)	0.0296 (13)	−0.0037 (10)	−0.0125 (10)	0.0024 (9)
C16	0.0456 (15)	0.0301 (14)	0.0440 (16)	−0.0123 (12)	−0.0168 (13)	−0.0054 (11)
C17	0.0372 (14)	0.0360 (14)	0.0312 (13)	0.0015 (11)	−0.0138 (11)	0.0058 (11)
C18	0.0429 (15)	0.0623 (19)	0.0343 (15)	−0.0128 (14)	−0.0221 (13)	0.0039 (13)
C19	0.0248 (11)	0.0318 (13)	0.0285 (12)	−0.0008 (10)	−0.0149 (10)	−0.0027 (10)
C20	0.0246 (11)	0.0281 (12)	0.0268 (12)	−0.0035 (9)	−0.0141 (10)	0.0001 (9)
C21	0.0276 (12)	0.0300 (13)	0.0304 (13)	−0.0050 (10)	−0.0154 (10)	0.0012 (10)
C22	0.0282 (12)	0.0442 (15)	0.0268 (13)	−0.0047 (11)	−0.0125 (10)	−0.0005 (11)
C23	0.0294 (12)	0.0357 (14)	0.0332 (13)	−0.0003 (10)	−0.0120 (11)	−0.0082 (11)
C24	0.0380 (14)	0.0314 (14)	0.0457 (16)	−0.0107 (11)	−0.0205 (13)	0.0011 (11)
C25	0.0552 (19)	0.0407 (17)	0.081 (2)	−0.0076 (15)	−0.0140 (18)	−0.0240 (16)
C26	0.0516 (18)	0.0476 (18)	0.0467 (18)	−0.0241 (15)	−0.0050 (14)	0.0070 (14)
C27	0.0329 (14)	0.0627 (19)	0.0280 (14)	−0.0047 (13)	−0.0079 (11)	−0.0018 (13)
N7	0.0429 (13)	0.0457 (14)	0.0328 (12)	−0.0045 (11)	−0.0142 (10)	−0.0079 (10)
O10	0.0632 (14)	0.0483 (13)	0.0406 (12)	0.0009 (11)	−0.0138 (10)	−0.0060 (9)
C28	0.095 (3)	0.067 (2)	0.053 (2)	0.008 (2)	−0.043 (2)	−0.0124 (17)
C29	0.0523 (18)	0.058 (2)	0.0531 (19)	−0.0166 (16)	−0.0153 (15)	−0.0070 (15)
C30	0.0431 (16)	0.0496 (18)	0.0372 (15)	−0.0060 (13)	−0.0064 (13)	−0.0176 (13)
O11	0.0832 (18)	0.0606 (16)	0.0525 (14)	−0.0037 (13)	−0.0231 (13)	−0.0055 (12)
N8	0.085 (2)	0.0335 (13)	0.0498 (15)	−0.0063 (13)	−0.0375 (15)	−0.0041 (11)
C31	0.162 (5)	0.055 (2)	0.075 (3)	−0.043 (3)	−0.070 (3)	0.017 (2)
C32	0.119 (3)	0.0432 (19)	0.061 (2)	−0.010 (2)	−0.042 (2)	−0.0128 (16)
C33	0.077 (2)	0.0359 (16)	0.057 (2)	0.0051 (15)	−0.0400 (18)	−0.0095 (14)

Geometric parameters (Å, º) top

Fe1—O2	1.9801 (15)	C12—C15	1.499 (3)
Fe1—O5	2.0071 (16)	C13—C14	1.388 (4)
Fe1—O8	2.0121 (16)	C13—C18	1.500 (3)
Fe1—O1	2.0342 (16)	C14—H14A	0.9500
Fe1—O7	2.0367 (16)	C16—H16A	0.9800
Fe1—O4	2.0483 (16)	C16—H16B	0.9800
C1—O1	1.295 (3)	C16—H16C	0.9800
C2—O2	1.321 (3)	C17—H17A	0.9800
O3—C6	1.228 (3)	C17—H17B	0.9800
C10—O4	1.290 (3)	C17—H17C	0.9800
C11—O5	1.316 (3)	C18—H18A	0.9800
O6—C15	1.234 (3)	C18—H18B	0.9800
C19—O7	1.298 (3)	C18—H18C	0.9800
C20—O8	1.315 (3)	C19—C23	1.395 (3)
O9—C24	1.237 (3)	C19—C20	1.437 (3)
N1—C4	1.363 (3)	C20—C21	1.394 (3)
N1—C3	1.384 (3)	C21—C24	1.498 (4)
N1—C8	1.477 (3)	C22—C23	1.384 (3)
N2—C6	1.326 (3)	C22—C27	1.502 (3)
N2—C7	1.453 (3)	C23—H23A	0.9500
N2—H2A	0.8800	C25—H25A	0.9800
N3—C13	1.348 (3)	C25—H25B	0.9800
N3—C12	1.392 (3)	C25—H25C	0.9800
N3—C17	1.481 (3)	C26—H26A	0.9800
N4—C15	1.331 (3)	C26—H26B	0.9800
N4—C16	1.459 (3)	C26—H26C	0.9800
N4—H4A	0.8800	C27—H27A	0.9800
N5—C22	1.352 (3)	C27—H27B	0.9800
N5—C21	1.394 (3)	C27—H27C	0.9800
N5—C26	1.483 (3)	N7—C30	1.334 (4)
N6—C24	1.327 (4)	N7—C28	1.447 (4)
N6—C25	1.444 (4)	N7—C29	1.450 (4)
N6—H6A	0.8800	O10—C30	1.226 (4)
C1—C5	1.392 (3)	C28—H28A	0.9800
C1—C2	1.436 (3)	C28—H28B	0.9800
C2—C3	1.380 (3)	C28—H28C	0.9800
C3—C6	1.505 (3)	C29—H29A	0.9800
C4—C5	1.381 (3)	C29—H29B	0.9800
C4—C9	1.499 (3)	C29—H29C	0.9800
C5—H5A	0.9500	C30—H30A	0.9500
C7—H7A	0.9800	O11—C33	1.208 (4)
C7—H7B	0.9800	N8—C33	1.329 (4)
C7—H7C	0.9800	N8—C32	1.446 (4)
C8—H8A	0.9800	N8—C31	1.450 (4)
C8—H8B	0.9800	C31—H31A	0.9800
C8—H8C	0.9800	C31—H31B	0.9800
C9—H9A	0.9800	C31—H31C	0.9800
C9—H9B	0.9800	C32—H32A	0.9800
C9—H9C	0.9800	C32—H32B	0.9800
C10—C14	1.390 (3)	C32—H32C	0.9800
C10—C11	1.453 (3)	C33—H33A	0.9500
C11—C12	1.385 (3)

O2—Fe1—O5	93.98 (6)	N4—C15—C12	118.0 (2)
O2—Fe1—O8	99.02 (7)	N4—C16—H16A	109.5
O5—Fe1—O8	166.59 (7)	N4—C16—H16B	109.5
O2—Fe1—O1	81.53 (6)	H16A—C16—H16B	109.5
O5—Fe1—O1	98.07 (7)	N4—C16—H16C	109.5
O8—Fe1—O1	87.16 (6)	H16A—C16—H16C	109.5
O2—Fe1—O7	93.14 (6)	H16B—C16—H16C	109.5
O5—Fe1—O7	96.30 (7)	N3—C17—H17A	109.5
O8—Fe1—O7	79.79 (6)	N3—C17—H17B	109.5
O1—Fe1—O7	164.98 (7)	H17A—C17—H17B	109.5
O2—Fe1—O4	169.33 (6)	N3—C17—H17C	109.5
O5—Fe1—O4	80.10 (6)	H17A—C17—H17C	109.5
O8—Fe1—O4	87.55 (6)	H17B—C17—H17C	109.5
O1—Fe1—O4	90.46 (6)	C13—C18—H18A	109.5
O7—Fe1—O4	96.32 (7)	C13—C18—H18B	109.5
C1—O1—Fe1	112.04 (14)	H18A—C18—H18B	109.5
C2—O2—Fe1	112.54 (13)	C13—C18—H18C	109.5
C10—O4—Fe1	112.76 (14)	H18A—C18—H18C	109.5
C11—O5—Fe1	113.43 (13)	H18B—C18—H18C	109.5
C19—O7—Fe1	112.58 (15)	O7—C19—C23	125.5 (2)
C20—O8—Fe1	113.46 (14)	O7—C19—C20	117.3 (2)
C4—N1—C3	121.22 (19)	C23—C19—C20	117.2 (2)
C4—N1—C8	119.4 (2)	O8—C20—C21	124.3 (2)
C3—N1—C8	119.3 (2)	O8—C20—C19	115.4 (2)
C6—N2—C7	122.2 (2)	C21—C20—C19	120.3 (2)
C6—N2—H2A	118.9	N5—C21—C20	119.0 (2)
C7—N2—H2A	118.9	N5—C21—C24	120.6 (2)
C13—N3—C12	121.4 (2)	C20—C21—C24	120.0 (2)
C13—N3—C17	118.1 (2)	N5—C22—C23	120.5 (2)
C12—N3—C17	120.4 (2)	N5—C22—C27	118.8 (2)
C15—N4—C16	120.2 (2)	C23—C22—C27	120.7 (2)
C15—N4—H4A	119.9	C22—C23—C19	121.4 (2)
C16—N4—H4A	119.9	C22—C23—H23A	119.3
C22—N5—C21	121.4 (2)	C19—C23—H23A	119.3
C22—N5—C26	117.6 (2)	O9—C24—N6	121.1 (3)
C21—N5—C26	120.9 (2)	O9—C24—C21	122.8 (3)
C24—N6—C25	122.2 (2)	N6—C24—C21	115.9 (2)
C24—N6—H6A	118.9	N6—C25—H25A	109.5
C25—N6—H6A	118.9	N6—C25—H25B	109.5
O1—C1—C5	125.4 (2)	H25A—C25—H25B	109.5
O1—C1—C2	116.7 (2)	N6—C25—H25C	109.5
C5—C1—C2	118.0 (2)	H25A—C25—H25C	109.5
O2—C2—C3	123.7 (2)	H25B—C25—H25C	109.5
O2—C2—C1	117.19 (19)	N5—C26—H26A	109.5
C3—C2—C1	119.1 (2)	N5—C26—H26B	109.5
C2—C3—N1	120.5 (2)	H26A—C26—H26B	109.5
C2—C3—C6	120.9 (2)	N5—C26—H26C	109.5
N1—C3—C6	118.44 (19)	H26A—C26—H26C	109.5
N1—C4—C5	119.5 (2)	H26B—C26—H26C	109.5
N1—C4—C9	119.3 (2)	C22—C27—H27A	109.5
C5—C4—C9	121.2 (2)	C22—C27—H27B	109.5
C4—C5—C1	121.7 (2)	H27A—C27—H27B	109.5
C4—C5—H5A	119.2	C22—C27—H27C	109.5
C1—C5—H5A	119.2	H27A—C27—H27C	109.5
O3—C6—N2	124.8 (2)	H27B—C27—H27C	109.5
O3—C6—C3	120.2 (2)	C30—N7—C28	122.1 (3)
N2—C6—C3	115.0 (2)	C30—N7—C29	120.7 (3)
N2—C7—H7A	109.5	C28—N7—C29	116.8 (3)
N2—C7—H7B	109.5	N7—C28—H28A	109.5
H7A—C7—H7B	109.5	N7—C28—H28B	109.5
N2—C7—H7C	109.5	H28A—C28—H28B	109.5
H7A—C7—H7C	109.5	N7—C28—H28C	109.5
H7B—C7—H7C	109.5	H28A—C28—H28C	109.5
N1—C8—H8A	109.5	H28B—C28—H28C	109.5
N1—C8—H8B	109.5	N7—C29—H29A	109.5
H8A—C8—H8B	109.5	N7—C29—H29B	109.5
N1—C8—H8C	109.5	H29A—C29—H29B	109.5
H8A—C8—H8C	109.5	N7—C29—H29C	109.5
H8B—C8—H8C	109.5	H29A—C29—H29C	109.5
C4—C9—H9A	109.5	H29B—C29—H29C	109.5
C4—C9—H9B	109.5	O10—C30—N7	124.9 (3)
H9A—C9—H9B	109.5	O10—C30—H30A	117.5
C4—C9—H9C	109.5	N7—C30—H30A	117.5
H9A—C9—H9C	109.5	C33—N8—C32	121.9 (3)
H9B—C9—H9C	109.5	C33—N8—C31	121.2 (3)
O4—C10—C14	125.6 (2)	C32—N8—C31	116.9 (3)
O4—C10—C11	116.6 (2)	N8—C31—H31A	109.5
C14—C10—C11	117.8 (2)	N8—C31—H31B	109.5
O5—C11—C12	125.2 (2)	H31A—C31—H31B	109.5
O5—C11—C10	116.04 (19)	N8—C31—H31C	109.5
C12—C11—C10	118.7 (2)	H31A—C31—H31C	109.5
C11—C12—N3	120.3 (2)	H31B—C31—H31C	109.5
C11—C12—C15	121.9 (2)	N8—C32—H32A	109.5
N3—C12—C15	117.03 (19)	N8—C32—H32B	109.5
N3—C13—C14	120.0 (2)	H32A—C32—H32B	109.5
N3—C13—C18	119.2 (2)	N8—C32—H32C	109.5
C14—C13—C18	120.8 (2)	H32A—C32—H32C	109.5
C13—C14—C10	121.6 (2)	H32B—C32—H32C	109.5
C13—C14—H14A	119.2	O11—C33—N8	125.0 (3)
C10—C14—H14A	119.2	O11—C33—H33A	117.5
O6—C15—N4	122.5 (2)	N8—C33—H33A	117.5
O6—C15—C12	119.4 (2)

C2—C3—C6—O3	−102.5 (3)	C20—C21—C24—O9	146.6 (3)
C11—C12—C15—O6	−135.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O6ⁱ	0.88	1.96	2.797 (3)	158
N4—H4A···O11	0.88	2.32	2.946 (3)	128
N4—H4A···O5	0.88	2.41	2.860 (3)	112
N6—H6A···O8	0.88	2.03	2.615 (3)	123

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	Fe(C₉H₁₁N₂O₃)₃·2C₃H₇NO
M_r	787.64
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	11.1137 (2), 13.0414 (3), 13.8382 (3)
α, β, γ (°)	79.1515 (10), 68.8106 (10), 79.7017 (9)
V (Å³)	1823.18 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.48
Crystal size (mm)	0.10 × 0.06 × 0.04

Data collection
Diffractometer	Bruker–Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.910, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	24188, 8323, 6063
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.126, 1.01
No. of reflections	8323
No. of parameters	492
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.49

Computer programs: Collect (Nonius, 2003), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXTL (Sheldrick, 2001), SHELXTL.

Selected bond lengths (Å) top

Fe1—O2	1.9801 (15)	C1—O1	1.295 (3)
Fe1—O5	2.0071 (16)	C2—O2	1.321 (3)
Fe1—O8	2.0121 (16)	C10—O4	1.290 (3)
Fe1—O1	2.0342 (16)	C11—O5	1.316 (3)
Fe1—O7	2.0367 (16)	C19—O7	1.298 (3)
Fe1—O4	2.0483 (16)	C20—O8	1.315 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O6ⁱ	0.88	1.96	2.797 (3)	158
N4—H4A···O11	0.88	2.32	2.946 (3)	128
N4—H4A···O5	0.88	2.41	2.860 (3)	112
N6—H6A···O8	0.88	2.03	2.615 (3)	123

Symmetry code: (i) −x, −y+1, −z+1.

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