Literature DB >> 21579668

Bis[2-(8-quinolylimino-meth-yl)phenolato-κN,N',O]iron(III) azide.

Yoshihiro Kojima, Kazuya Kato, Yuuki Yamamoto, Katsuya Inoue, Shinya Hayami.

Abstract

The title compound, [Fe(C(16)H(11)N(2)O)(2)]N(3), consists of a [Fe(qsal)(2)](+) cation [Hqsal = N-(8-quinol-yl)salicylaldimine] and an azide anion. The Fe(III) ion, lying on a twofold rotation axis, is coordinated by four N atoms and two O atoms from two tridentate qsal ligands in an octa-hedral geometry. The mol-ecules are connected into a three-dimensional network by inter-molecular C-H⋯N and C-H⋯O inter-actions. π-π inter-actions [inter-planar distance = 3.58 (1) Å] between the quinoline rings of adjacent mol-ecules further stabilize the crystal structure.

Entities: Chemical Disease Species

Year: 2010 PMID： 21579668 PMCID： PMC2979845 DOI： 10.1107/S1600536810002783

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For Fe(III) complexes with qsal ligands, see: Hayami et al. (2001 ▶); Takahashi et al. (2006 ▶). For bond lengths in Fe(III) complexes, see: Nihei et al. (2007 ▶).

Experimental

Crystal data

[Fe(C16H11N2O)2]N3 M = 592.42 Monoclinic, a = 11.3717 (8) Å b = 10.1190 (8) Å c = 11.7734 (6) Å β = 109.3542 (15)° V = 1278.21 (15) Å3 Z = 2 Mo Kα radiation μ = 0.64 mm−1 T = 200 K 0.50 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.741, T max = 0.883 11530 measured reflections 2929 independent reflections 2556 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.031 wR(F 2) = 0.104 S = 0.86 2929 reflections 191 parameters H-atom parameters constrained Δρmax = 0.34 e Å−3 Δρmin = −0.39 e Å−3 Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalClear (Rigaku, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Yadokari-XG (Wakita, 2000 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810002783/hy2271sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002783/hy2271Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Fe(C₁₆H₁₁N₂O)₂]N₃	F(000) = 610
M_r = 592.42	D_x = 1.539 Mg m⁻³
Monoclinic, P2/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yac	Cell parameters from 11530 reflections
a = 11.3717 (8) Å	θ = 1.8–27.5°
b = 10.1190 (8) Å	µ = 0.64 mm⁻¹
c = 11.7734 (6) Å	T = 200 K
β = 109.3542 (15)°	Block, black
V = 1278.21 (15) Å³	0.50 × 0.20 × 0.20 mm
Z = 2

Rigaku R-AXIS RAPID diffractometer	2929 independent reflections
Radiation source: rotation anode	2556 reflections with I > 2σ(I)
graphite	R_int = 0.026
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = 0→14
T_min = 0.741, T_max = 0.883	k = 0→13
11530 measured reflections	l = −15→14

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 0.86	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
2929 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

	x	y	z	U_iso*/U_eq
Fe1	0.2500	0.12760 (3)	0.7500	0.01593 (12)
O1	0.13778 (10)	0.00441 (11)	0.77255 (10)	0.0230 (2)
N1	0.35553 (12)	0.13158 (12)	0.91699 (11)	0.0181 (3)
N2	0.36114 (11)	0.27008 (12)	0.73375 (11)	0.0184 (3)
N3	0.2500	0.28128 (19)	1.2500	0.0279 (4)
N4	0.26580 (17)	0.28132 (18)	1.15630 (15)	0.0433 (4)
C1	0.14342 (14)	−0.05156 (14)	0.87550 (13)	0.0211 (3)
C2	0.04475 (17)	−0.13609 (16)	0.87415 (16)	0.0286 (4)
H2	−0.0224	−0.1491	0.8012	0.034*
C3	0.04411 (18)	−0.20050 (19)	0.97754 (16)	0.0352 (4)
H3	−0.0236	−0.2569	0.9745	0.042*
C4	0.1411 (2)	−0.1841 (2)	1.08613 (16)	0.0395 (5)
H4	0.1409	−0.2307	1.1561	0.047*
C5	0.23689 (18)	−0.09964 (19)	1.09040 (15)	0.0321 (4)
H5	0.3022	−0.0865	1.1646	0.038*
C6	0.24043 (15)	−0.03176 (15)	0.98671 (14)	0.0230 (3)
C7	0.34174 (14)	0.05762 (15)	1.00231 (13)	0.0218 (3)
H7	0.4031	0.0636	1.0799	0.026*
C8	0.45447 (14)	0.22483 (14)	0.94235 (13)	0.0207 (3)
C9	0.54613 (16)	0.24933 (17)	1.05052 (15)	0.0293 (4)
H9	0.5493	0.1992	1.1197	0.035*
C10	0.63516 (17)	0.3487 (2)	1.05877 (17)	0.0355 (4)
H10	0.6988	0.3639	1.1337	0.043*
C11	0.63210 (16)	0.42458 (18)	0.96008 (16)	0.0323 (4)
H11	0.6924	0.4920	0.9679	0.039*
C12	0.53937 (15)	0.40166 (16)	0.84810 (15)	0.0252 (3)
C13	0.52736 (15)	0.47520 (17)	0.74226 (16)	0.0291 (4)
H13	0.5829	0.5460	0.7443	0.035*
C14	0.43587 (15)	0.44350 (16)	0.63807 (15)	0.0272 (3)
H14	0.4270	0.4925	0.5669	0.033*
C15	0.35431 (14)	0.33827 (16)	0.63543 (14)	0.0221 (3)
H15	0.2926	0.3153	0.5613	0.027*
C16	0.45197 (13)	0.30040 (15)	0.83972 (13)	0.0194 (3)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.01757 (17)	0.01657 (17)	0.01266 (17)	0.000	0.00365 (11)	0.000
O1	0.0252 (5)	0.0240 (5)	0.0169 (5)	−0.0063 (4)	0.0032 (4)	0.0021 (4)
N1	0.0187 (6)	0.0199 (6)	0.0149 (6)	0.0007 (4)	0.0045 (5)	−0.0004 (4)
N2	0.0174 (5)	0.0205 (6)	0.0174 (6)	0.0000 (5)	0.0059 (5)	0.0001 (4)
N3	0.0242 (9)	0.0256 (10)	0.0281 (10)	0.000	0.0009 (8)	0.000
N4	0.0472 (10)	0.0516 (10)	0.0297 (9)	−0.0174 (8)	0.0110 (7)	−0.0039 (7)
C1	0.0265 (7)	0.0198 (7)	0.0175 (7)	−0.0006 (6)	0.0079 (6)	0.0011 (5)
C2	0.0292 (8)	0.0309 (9)	0.0244 (8)	−0.0087 (7)	0.0071 (7)	0.0009 (6)
C3	0.0408 (10)	0.0377 (9)	0.0293 (9)	−0.0159 (8)	0.0147 (8)	0.0011 (7)
C4	0.0536 (11)	0.0434 (11)	0.0224 (8)	−0.0161 (9)	0.0138 (8)	0.0049 (7)
C5	0.0408 (10)	0.0356 (9)	0.0166 (8)	−0.0079 (8)	0.0052 (7)	0.0038 (6)
C6	0.0286 (8)	0.0216 (7)	0.0188 (7)	−0.0012 (6)	0.0080 (6)	0.0010 (6)
C7	0.0247 (7)	0.0223 (7)	0.0155 (7)	0.0008 (6)	0.0027 (6)	0.0006 (5)
C8	0.0195 (6)	0.0215 (7)	0.0199 (7)	−0.0003 (5)	0.0049 (5)	−0.0024 (5)
C9	0.0290 (8)	0.0341 (9)	0.0215 (8)	−0.0055 (7)	0.0039 (6)	−0.0012 (6)
C10	0.0284 (9)	0.0451 (10)	0.0254 (9)	−0.0118 (8)	−0.0012 (7)	−0.0045 (7)
C11	0.0282 (8)	0.0346 (9)	0.0315 (9)	−0.0123 (7)	0.0064 (7)	−0.0049 (7)
C12	0.0217 (7)	0.0249 (8)	0.0288 (9)	−0.0027 (6)	0.0080 (6)	−0.0026 (6)
C13	0.0280 (8)	0.0266 (8)	0.0346 (9)	−0.0066 (7)	0.0129 (7)	0.0012 (7)
C14	0.0283 (8)	0.0263 (8)	0.0295 (8)	−0.0013 (6)	0.0128 (7)	0.0066 (6)
C15	0.0204 (7)	0.0248 (7)	0.0213 (7)	0.0005 (6)	0.0071 (6)	0.0035 (6)
C16	0.0172 (6)	0.0203 (7)	0.0202 (7)	−0.0001 (5)	0.0054 (5)	−0.0020 (5)

Fe1—O1	1.8648 (11)	C5—H5	0.9500
Fe1—N1	1.9347 (13)	C6—C7	1.428 (2)
Fe1—N2	1.9680 (12)	C7—H7	0.9500
O1—C1	1.3201 (17)	C8—C9	1.375 (2)
N1—C7	1.3031 (19)	C8—C16	1.422 (2)
N1—C8	1.4222 (19)	C9—C10	1.407 (2)
N2—C15	1.3276 (19)	C9—H9	0.9500
N2—C16	1.3650 (18)	C10—C11	1.384 (3)
N3—N4	1.1750 (17)	C10—H10	0.9500
N3—N4ⁱ	1.1750 (17)	C11—C12	1.408 (2)
C1—C2	1.407 (2)	C11—H11	0.9500
C1—C6	1.419 (2)	C12—C13	1.418 (2)
C2—C3	1.383 (2)	C12—C16	1.408 (2)
C2—H2	0.9500	C13—H13	0.9500
C3—H3	0.9500	C14—C13	1.358 (2)
C4—C3	1.394 (3)	C15—C14	1.406 (2)
C4—C5	1.372 (3)	C14—H14	0.9500
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.413 (2)

O1—Fe1—O1ⁱⁱ	96.10 (7)	C4—C5—H5	119.3
O1—Fe1—N1	95.31 (5)	C6—C5—H5	119.3
O1—Fe1—N1ⁱⁱ	86.29 (5)	C1—C6—C5	119.50 (14)
O1ⁱⁱ—Fe1—N1	86.29 (5)	C1—C6—C7	123.74 (14)
O1ⁱⁱ—Fe1—N1ⁱⁱ	95.31 (5)	C5—C6—C7	116.72 (14)
O1—Fe1—N2	174.51 (5)	N1—C7—C6	124.24 (14)
O1—Fe1—N2ⁱⁱ	89.09 (5)	N1—C7—H7	117.9
O1ⁱⁱ—Fe1—N2	89.09 (5)	C6—C7—H7	117.9
O1ⁱⁱ—Fe1—N2ⁱⁱ	174.51 (5)	N1—C8—C9	128.20 (14)
N1ⁱⁱ—Fe1—N1	177.62 (7)	N1—C8—C16	112.74 (13)
N1—Fe1—N2	83.19 (5)	C9—C8—C16	119.05 (14)
N1—Fe1—N2ⁱⁱ	95.05 (5)	C8—C9—C10	120.01 (16)
N1ⁱⁱ—Fe1—N2	95.05 (5)	C8—C9—H9	120.0
N1ⁱⁱ—Fe1—N2ⁱⁱ	83.19 (5)	C10—C9—H9	120.0
N2ⁱⁱ—Fe1—N2	85.79 (7)	C9—C10—C11	121.43 (16)
Fe1—O1—C1	126.18 (10)	C9—C10—H10	119.3
Fe1—N1—C7	125.36 (11)	C11—C10—H10	119.3
Fe1—N1—C8	114.10 (10)	C10—C11—C12	119.83 (16)
C7—N1—C8	120.54 (13)	C10—C11—H11	120.1
Fe1—N2—C15	127.71 (10)	C12—C11—H11	120.1
Fe1—N2—C16	113.05 (9)	C11—C12—C13	124.08 (16)
C15—N2—C16	119.21 (13)	C11—C12—C16	118.54 (15)
N4—N3—N4ⁱ	180.0 (3)	C13—C12—C16	117.39 (15)
O1—C1—C2	117.04 (14)	C12—C13—C14	119.44 (15)
O1—C1—C6	124.95 (14)	C14—C13—H13	120.3
C2—C1—C6	118.00 (14)	C12—C13—H13	120.3
C1—C2—C3	120.89 (16)	C13—C14—C15	120.09 (15)
C1—C2—H2	119.6	C13—C14—H14	120.0
C3—C2—H2	119.6	C15—C14—H14	120.0
C2—C3—C4	121.17 (16)	N2—C15—C14	121.80 (14)
C2—C3—H3	119.4	N2—C15—H15	119.1
C4—C3—H3	119.4	C14—C15—H15	119.1
C3—C4—C5	119.02 (16)	N2—C16—C12	122.03 (14)
C5—C4—H4	120.5	N2—C16—C8	116.85 (13)
C3—C4—H4	120.5	C8—C16—C12	121.12 (14)
C4—C5—C6	121.37 (16)

O1ⁱⁱ—Fe1—O1—C1	86.71 (12)	C15—N2—C16—C12	−0.3 (2)
N1—Fe1—O1—C1	−0.11 (13)	O1—C1—C2—C3	178.95 (16)
N1ⁱⁱ—Fe1—O1—C1	−178.34 (13)	C6—C1—C2—C3	−1.6 (3)
O1—Fe1—N1—C7	3.95 (13)	O1—C1—C6—C5	−178.78 (16)
O1ⁱⁱ—Fe1—N1—C7	−91.84 (13)	O1—C1—C6—C7	3.5 (2)
O1—Fe1—N1—C8	−176.17 (10)	C2—C1—C6—C5	1.9 (2)
O1ⁱⁱ—Fe1—N1—C8	88.04 (10)	C2—C1—C6—C7	−175.91 (15)
N2—Fe1—N1—C7	178.64 (13)	C1—C2—C3—C4	−0.2 (3)
N2ⁱⁱ—Fe1—N1—C7	93.51 (13)	C2—C3—C4—C5	1.7 (3)
N2—Fe1—N1—C8	−1.49 (10)	C3—C4—C5—C6	−1.5 (3)
N2ⁱⁱ—Fe1—N1—C8	−86.62 (10)	C4—C5—C6—C1	−0.3 (3)
O1ⁱⁱ—Fe1—N2—C15	95.66 (13)	C4—C5—C6—C7	177.60 (17)
N1—Fe1—N2—C15	−177.97 (13)	C1—C6—C7—N1	0.8 (2)
N1ⁱⁱ—Fe1—N2—C15	0.41 (13)	C5—C6—C7—N1	−177.02 (15)
N2ⁱⁱ—Fe1—N2—C15	−82.36 (13)	N1—C8—C9—C10	−178.44 (16)
O1ⁱⁱ—Fe1—N2—C16	−86.28 (10)	C16—C8—C9—C10	0.5 (2)
N1—Fe1—N2—C16	0.09 (10)	N1—C8—C16—N2	−2.56 (19)
N1ⁱⁱ—Fe1—N2—C16	178.47 (10)	N1—C8—C16—C12	177.32 (13)
N2ⁱⁱ—Fe1—N2—C16	95.70 (11)	C9—C8—C16—N2	178.36 (14)
Fe1—O1—C1—C2	176.17 (11)	C9—C8—C16—C12	−1.8 (2)
Fe1—O1—C1—C6	−3.2 (2)	C8—C9—C10—C11	0.8 (3)
Fe1—N1—C7—C6	−4.7 (2)	C9—C10—C11—C12	−0.9 (3)
C8—N1—C7—C6	175.48 (14)	C10—C11—C12—C13	179.10 (17)
Fe1—N1—C8—C9	−178.46 (14)	C10—C11—C12—C16	−0.4 (3)
Fe1—N1—C8—C16	2.56 (16)	C11—C12—C13—C14	178.80 (17)
C7—N1—C8—C9	1.4 (2)	C16—C12—C13—C14	−1.7 (2)
C7—N1—C8—C16	−177.56 (13)	C11—C12—C16—N2	−178.43 (15)
Fe1—N2—C15—C14	176.08 (11)	C11—C12—C16—C8	1.7 (2)
C16—N2—C15—C14	−1.9 (2)	C13—C12—C16—N2	2.1 (2)
Fe1—N2—C16—C8	1.35 (16)	C13—C12—C16—C8	−177.80 (14)
Fe1—N2—C16—C12	−178.52 (11)	C12—C13—C14—C15	−0.3 (3)
C15—N2—C16—C8	179.59 (13)	C13—C14—C15—N2	2.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1ⁱⁱⁱ	0.95	2.70	3.565 (2)	151
C15—H15···N4ⁱⁱ	0.95	2.45	3.299 (2)	149

Table 1

Selected bond lengths (Å)

Fe1—O1	1.8648 (11)
Fe1—N1	1.9347 (13)
Fe1—N2	1.9680 (12)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1ⁱ	0.95	2.70	3.565 (2)	151
C15—H15⋯N4ⁱⁱ	0.95	2.45	3.299 (2)	149

Symmetry codes: (i) ; (ii) .

3 in total

1. Iron(III) spin-crossover compounds with a wide apparent thermal hysteresis around room temperature.

Authors: S Hayami; Z Gu; H Yoshiki; A Fujishima; O Sato
Journal: J Am Chem Soc Date: 2001-11-28 Impact factor: 15.419

2. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

3. Electrical conductivity modulation coupled to a high-spin-low-spin conversion in the molecular system [FeIII(qsal)2][Ni(dmit)2]3.CH3CN.H2O.

Authors: Kazuyuki Takahashi; Heng-Bo Cui; Yoshinori Okano; Hayao Kobayashi; Yasuaki Einaga; Osamu Sato
Journal: Inorg Chem Date: 2006-07-24 Impact factor: 5.165

3 in total