Dichlorido{1-[(2-hy­droxy­eth­yl)imino­meth­yl]-2-naphtho­lato}pyridine­iron(III) pyridine monosolvate

Liu, S.; Yang, J.; Lv, L.; Li, D.

doi:10.1107/S1600536810046623

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page m1585

https://doi.org/10.1107/S1600536810046623

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Dichlorido{1-[(2-hydroxyethyl)iminomethyl]-2-naphtholato}pyridineiron(III) pyridine monosolvate

Shizheng Liu,^a Jie Yang,^a Lei Lv ^a and Dacheng Li ^a ^*

^aSchool of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: lidacheng@lcu.edu.cn

(Received 1 November 2010; accepted 11 November 2010; online 17 November 2010)

In the title complex, [Fe(C₁₃H₁₂NO₂)Cl₂(C₅H₅N)]·C₅H₅N, the iron(III) atom is six-coordinated by the N and O atoms from the Schiff base ligand, the N atom from a pyridine molecule and two chloride anions in a distorted octahedral geometry. The crystal packing is stabilized by intermolecular O—H⋯N hydrogen bonds and C—H⋯π interactions.

Related literature

For the synthesis and applications of magnetic complexes, see: Oshio et al. (2004 ); Aromí & Brechin (2006 ). For related structures, see: Goodwin et al. (2000 ); Qian et al. (2008 ); Hoshino et al. (2009 ).

Experimental

Crystal data

[Fe(C₁₃H₁₂NO₂)Cl₂(C₅H₅N)]·C₅H₅N
M_r = 499.19
Monoclinic, P 2₁
a = 7.8590 (6) Å
b = 10.0153 (11) Å
c = 14.4884 (16) Å
β = 90.123 (1)°
V = 1140.4 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.92 mm⁻¹
T = 298 K
0.48 × 0.44 × 0.37 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Siemens, 1996 ) T_min = 0.666, T_max = 0.727
5726 measured reflections
3395 independent reflections
3143 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.085
S = 1.00
3395 reflections
281 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.19 e Å⁻³
Absolute structure: Flack (1983 ), 1265 Friedel pairs
Flack parameter: 0.02 (2)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3	0.82	1.81	2.617 (4)	168
C12—H12⋯Cgⁱ	0.93	2.71	3.594 (5)	159
C16—H16⋯Cgⁱⁱ	0.93	2.78	3.653 (6)	157
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z]$ ; (ii) x, y+1, z.

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810046623/rz2519sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046623/rz2519Isup2.hkl

checkCIF report

Comment top

The considerable current interest in magnetic complexes arises from their relevance in diverse fields ranging from bioinorganic chemistry to molecular magnetic materials (Oshio et al., 2004; Aromí et al., 2006). We report here the synthesis and crystal structure of the title compound.

In the title complex (Fig. 1), the tridentate Schiff base ligand is derived from the condensation of 2-hydroxy-1-naphthaldehyde and ethanolamine. The iron(III) metal centre is six-coordinate by the N and O atoms from the Schiff base ligand, the N atom from a pyridine molecule and two chloride anions in a distorted octahedral geometry. The Fe–O(alkoxo) bond length [Fe1–O1 = 2.105 (2) Å] is longer than the Fe–O(phenoxo) distance [Fe1–O2 = 1.897 (2) Å], which lies well within the range of values reported in the literature (Goodwin et al., 2000; Qian et al., 2008; Hoshino et al., 2009). In the crystal structure, complex molecules and pyridine solvent molecules are linked into a three-dimensional network by O—H···N hydrogen bonds and C—H···π interactions (Table 1).

Related literature top

For the synthesis and applications of magnetic complexes, see: Oshio et al. (2004); Aromí & Brechin, 2006. For related structures, see: Goodwin et al. (2000); Qian et al. (2008); Hoshino et al. (2009).

Experimental top

Ethanolamine (1 mmol, 61.08 mg) was dissolved in methanol (10 ml) and added dropwise to a methanol solution of 2-hydroxy-1-naphthaldehyde (1 mmol, 172.19 mg). The mixture was then stirred at 323 K for 2 h. Subsequently, an MeCN/Py solution "(3:1 v/v, 4 ml) of FeCl₃.6H₂O(1 mmol, 270.29 mg) was added dropwise and stirred for another 7 h. The resulting black solution was filtrated and was allowed to stand at room temperature for about one week, whereupon block crystals suitable for X-ray diffraction analysis were obtained.

Structure description top

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids.

Dichlorido{1-[(2-hydroxyethyl)iminomethyl]-2-naphtholato}pyridineiron(III) pyridine monosolvate top

Crystal data top

[Fe(C₁₃H₁₂NO₂)Cl₂(C₅H₅N)]·C₅H₅N	F(000) = 514
M_r = 499.19	D_x = 1.454 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3504 reflections
a = 7.8590 (6) Å	θ = 2.5–28.0°
b = 10.0153 (11) Å	µ = 0.92 mm⁻¹
c = 14.4884 (16) Å	T = 298 K
β = 90.123 (1)°	Block, black
V = 1140.4 (2) Å³	0.48 × 0.44 × 0.37 mm
Z = 2

Data collection top

Bruker SMART 1000 CCD diffractometer	3395 independent reflections
Radiation source: fine-focus sealed tube	3143 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
phi and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −8→9
T_min = 0.666, T_max = 0.727	k = −11→8
5726 measured reflections	l = −17→17

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)] = 0.032	H-atom parameters constrained
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0476P)² + 0.5289P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
3395 reflections	Δρ_max = 0.25 e Å⁻³
281 parameters	Δρ_min = −0.19 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1265 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (2)

Crystal data top

[Fe(C₁₃H₁₂NO₂)Cl₂(C₅H₅N)]·C₅H₅N	V = 1140.4 (2) Å³
M_r = 499.19	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.8590 (6) Å	µ = 0.92 mm⁻¹
b = 10.0153 (11) Å	T = 298 K
c = 14.4884 (16) Å	0.48 × 0.44 × 0.37 mm
β = 90.123 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	3395 independent reflections
Absorption correction: multi-scan (SADABS; Siemens, 1996)	3143 reflections with I > 2σ(I)
T_min = 0.666, T_max = 0.727	R_int = 0.021
5726 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.085	Δρ_max = 0.25 e Å⁻³
S = 1.00	Δρ_min = −0.19 e Å⁻³
3395 reflections	Absolute structure: Flack (1983), 1265 Friedel pairs
281 parameters	Absolute structure parameter: 0.02 (2)
1 restraint

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Fe1	0.54656 (5)	0.51232 (5)	0.28032 (3)	0.03179 (13)
Cl1	0.81839 (12)	0.59516 (12)	0.27394 (7)	0.0505 (3)
Cl2	0.61339 (13)	0.29636 (11)	0.33678 (7)	0.0486 (3)
N1	0.2862 (3)	0.4752 (3)	0.30300 (17)	0.0321 (7)
N2	0.4541 (4)	0.7190 (4)	0.2447 (2)	0.0386 (7)
N3	0.7698 (4)	0.5286 (4)	0.52783 (19)	0.0458 (8)
O1	0.5126 (3)	0.5757 (3)	0.41754 (15)	0.0374 (6)
H1	0.5968	0.5524	0.4469	0.056*
O2	0.5074 (3)	0.4537 (3)	0.15755 (16)	0.0386 (6)
C1	0.3621 (4)	0.5234 (5)	0.4608 (2)	0.0434 (9)
H1A	0.3330	0.5757	0.5149	0.052*
H1B	0.3798	0.4315	0.4796	0.052*
C2	0.2222 (4)	0.5320 (5)	0.3892 (2)	0.0409 (10)
H2A	0.1231	0.4827	0.4098	0.049*
H2B	0.1894	0.6244	0.3798	0.049*
C3	0.1855 (4)	0.4104 (4)	0.2498 (2)	0.0331 (8)
H3	0.0734	0.4006	0.2690	0.040*
C4	0.2316 (4)	0.3513 (4)	0.1627 (2)	0.0309 (8)
C5	0.3927 (4)	0.3731 (4)	0.1223 (2)	0.0334 (8)
C6	0.4347 (5)	0.3075 (5)	0.0381 (2)	0.0440 (10)
H6	0.5403	0.3227	0.0113	0.053*
C7	0.3239 (5)	0.2239 (5)	−0.0032 (2)	0.0505 (11)
H7	0.3564	0.1808	−0.0572	0.061*
C8	0.1613 (5)	0.1997 (4)	0.0327 (2)	0.0419 (10)
C9	0.1090 (5)	0.2669 (4)	0.1152 (2)	0.0330 (8)
C10	−0.0580 (5)	0.2445 (4)	0.1469 (3)	0.0431 (9)
H10	−0.0968	0.2911	0.1982	0.052*
C11	−0.1640 (6)	0.1561 (5)	0.1041 (3)	0.0566 (12)
H11	−0.2733	0.1426	0.1268	0.068*
C12	−0.1089 (6)	0.0855 (6)	0.0261 (3)	0.0632 (14)
H12	−0.1796	0.0221	−0.0011	0.076*
C13	0.0459 (6)	0.1095 (5)	−0.0094 (3)	0.0576 (12)
H13	0.0783	0.0656	−0.0631	0.069*
C14	0.3280 (5)	0.7367 (5)	0.1839 (3)	0.0496 (10)
H14	0.2786	0.6622	0.1565	0.060*
C15	0.2690 (7)	0.8615 (6)	0.1604 (3)	0.0659 (14)
H15	0.1814	0.8708	0.1177	0.079*
C16	0.3409 (7)	0.9727 (5)	0.2009 (4)	0.0731 (16)
H16	0.3043	1.0580	0.1851	0.088*
C17	0.4661 (7)	0.9548 (5)	0.2644 (4)	0.0635 (13)
H17	0.5147	1.0279	0.2940	0.076*
C18	0.5204 (5)	0.8271 (5)	0.2843 (3)	0.0509 (10)
H18	0.6071	0.8160	0.3274	0.061*
C19	0.8321 (6)	0.4104 (5)	0.5477 (3)	0.0588 (13)
H19	0.7821	0.3355	0.5211	0.071*
C20	0.9701 (7)	0.3926 (6)	0.6070 (4)	0.0650 (14)
H20	1.0113	0.3077	0.6200	0.078*
C21	1.0421 (5)	0.5014 (8)	0.6448 (3)	0.0656 (14)
H21	1.1334	0.4929	0.6852	0.079*
C22	0.9803 (7)	0.6227 (7)	0.6233 (4)	0.0805 (19)
H22	1.0306	0.6991	0.6476	0.097*
C23	0.8438 (7)	0.6334 (6)	0.5658 (4)	0.0663 (14)
H23	0.8009	0.7178	0.5527	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0295 (2)	0.0306 (3)	0.0353 (2)	0.0020 (2)	−0.00537 (16)	−0.0014 (2)
Cl1	0.0305 (4)	0.0524 (7)	0.0685 (6)	−0.0014 (4)	−0.0044 (4)	−0.0056 (5)
Cl2	0.0574 (6)	0.0332 (5)	0.0551 (6)	0.0102 (5)	−0.0071 (4)	0.0020 (4)
N1	0.0296 (14)	0.038 (2)	0.0290 (13)	0.0046 (12)	−0.0029 (11)	−0.0044 (12)
N2	0.0401 (17)	0.034 (2)	0.0420 (16)	0.0029 (15)	−0.0066 (13)	0.0025 (15)
N3	0.0476 (17)	0.046 (2)	0.0432 (16)	−0.0030 (18)	−0.0118 (13)	0.0028 (18)
O1	0.0377 (13)	0.0390 (16)	0.0354 (12)	0.0012 (11)	−0.0105 (10)	−0.0038 (11)
O2	0.0354 (13)	0.0449 (17)	0.0355 (12)	−0.0024 (11)	−0.0012 (10)	−0.0040 (11)
C1	0.0451 (18)	0.053 (3)	0.0323 (16)	0.001 (2)	0.0004 (13)	−0.005 (2)
C2	0.0336 (17)	0.051 (3)	0.0381 (17)	0.0047 (18)	−0.0013 (13)	−0.0170 (19)
C3	0.0307 (17)	0.032 (2)	0.0366 (18)	0.0043 (16)	−0.0019 (14)	0.0004 (16)
C4	0.0349 (18)	0.028 (2)	0.0294 (16)	0.0088 (15)	−0.0046 (14)	0.0009 (14)
C5	0.0358 (18)	0.033 (2)	0.0313 (17)	0.0065 (16)	−0.0076 (14)	0.0028 (15)
C6	0.0405 (19)	0.060 (3)	0.0319 (18)	0.006 (2)	0.0015 (15)	−0.0043 (19)
C7	0.060 (2)	0.060 (3)	0.0319 (19)	0.011 (2)	−0.0023 (17)	−0.014 (2)
C8	0.050 (2)	0.042 (3)	0.0339 (18)	0.002 (2)	−0.0114 (16)	−0.0019 (17)
C9	0.0387 (18)	0.029 (2)	0.0310 (16)	0.0043 (15)	−0.0086 (14)	−0.0003 (14)
C10	0.040 (2)	0.047 (3)	0.042 (2)	−0.0033 (18)	−0.0111 (16)	−0.0038 (18)
C11	0.049 (2)	0.066 (3)	0.056 (2)	−0.011 (2)	−0.016 (2)	0.001 (2)
C12	0.071 (3)	0.064 (3)	0.055 (3)	−0.020 (3)	−0.026 (2)	−0.010 (2)
C13	0.074 (3)	0.054 (3)	0.044 (2)	−0.002 (2)	−0.019 (2)	−0.018 (2)
C14	0.053 (2)	0.046 (3)	0.049 (2)	0.010 (2)	−0.0076 (19)	0.007 (2)
C15	0.070 (3)	0.069 (4)	0.058 (3)	0.027 (3)	−0.006 (2)	0.012 (3)
C16	0.094 (4)	0.047 (4)	0.078 (3)	0.028 (3)	0.015 (3)	0.021 (3)
C17	0.076 (3)	0.029 (2)	0.085 (3)	0.000 (2)	0.011 (3)	0.000 (2)
C18	0.051 (2)	0.037 (3)	0.065 (3)	−0.001 (2)	−0.0052 (19)	−0.001 (2)
C19	0.060 (3)	0.049 (3)	0.067 (3)	−0.008 (2)	−0.017 (2)	0.001 (2)
C20	0.063 (3)	0.058 (4)	0.074 (3)	0.005 (3)	−0.011 (2)	0.018 (3)
C21	0.042 (2)	0.099 (5)	0.056 (2)	0.012 (3)	−0.0130 (17)	−0.011 (3)
C22	0.061 (3)	0.091 (5)	0.089 (4)	−0.002 (3)	−0.021 (3)	−0.036 (4)
C23	0.066 (3)	0.049 (3)	0.084 (3)	0.009 (3)	−0.018 (3)	−0.012 (3)

Geometric parameters (Å, º) top

Fe1—O2	1.897 (2)	C8—C13	1.417 (6)
Fe1—O1	2.105 (2)	C8—C9	1.433 (5)
Fe1—N1	2.106 (3)	C9—C10	1.409 (5)
Fe1—N2	2.254 (3)	C10—C11	1.364 (6)
Fe1—Cl1	2.2938 (10)	C10—H10	0.9300
Fe1—Cl2	2.3709 (12)	C11—C12	1.403 (7)
N1—C3	1.280 (4)	C11—H11	0.9300
N1—C2	1.462 (4)	C12—C13	1.344 (7)
N2—C18	1.331 (6)	C12—H12	0.9300
N2—C14	1.336 (5)	C13—H13	0.9300
N3—C19	1.312 (7)	C14—C15	1.375 (7)
N3—C23	1.319 (6)	C14—H14	0.9300
O1—C1	1.439 (4)	C15—C16	1.379 (8)
O1—H1	0.8200	C15—H15	0.9300
O2—C5	1.313 (4)	C16—C17	1.357 (7)
C1—C2	1.513 (4)	C16—H16	0.9300
C1—H1A	0.9700	C17—C18	1.379 (6)
C1—H1B	0.9700	C17—H17	0.9300
C2—H2A	0.9700	C18—H18	0.9300
C2—H2B	0.9700	C19—C20	1.393 (7)
C3—C4	1.440 (5)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.344 (9)
C4—C5	1.414 (5)	C20—H20	0.9300
C4—C9	1.455 (5)	C21—C22	1.345 (9)
C5—C6	1.424 (5)	C21—H21	0.9300
C6—C7	1.348 (6)	C22—C23	1.361 (8)
C6—H6	0.9300	C22—H22	0.9300
C7—C8	1.402 (6)	C23—H23	0.9300
C7—H7	0.9300

O2—Fe1—O1	163.37 (10)	C6—C7—H7	119.0
O2—Fe1—N1	86.33 (10)	C8—C7—H7	119.0
O1—Fe1—N1	77.32 (9)	C7—C8—C13	122.2 (4)
O2—Fe1—N2	91.01 (11)	C7—C8—C9	119.5 (3)
O1—Fe1—N2	84.14 (11)	C13—C8—C9	118.3 (4)
N1—Fe1—N2	83.39 (11)	C10—C9—C8	117.8 (3)
O2—Fe1—Cl1	102.90 (8)	C10—C9—C4	123.7 (3)
O1—Fe1—Cl1	92.81 (7)	C8—C9—C4	118.5 (3)
N1—Fe1—Cl1	167.24 (9)	C11—C10—C9	121.6 (4)
N2—Fe1—Cl1	87.61 (8)	C11—C10—H10	119.2
O2—Fe1—Cl2	94.40 (9)	C9—C10—H10	119.2
O1—Fe1—Cl2	88.73 (8)	C10—C11—C12	120.3 (4)
N1—Fe1—Cl2	90.00 (9)	C10—C11—H11	119.9
N2—Fe1—Cl2	171.18 (9)	C12—C11—H11	119.9
Cl1—Fe1—Cl2	97.95 (4)	C13—C12—C11	119.9 (4)
C3—N1—C2	119.9 (3)	C13—C12—H12	120.0
C3—N1—Fe1	126.5 (2)	C11—C12—H12	120.0
C2—N1—Fe1	113.6 (2)	C12—C13—C8	121.9 (4)
C18—N2—C14	117.8 (4)	C12—C13—H13	119.0
C18—N2—Fe1	121.5 (3)	C8—C13—H13	119.0
C14—N2—Fe1	120.7 (3)	N2—C14—C15	122.2 (5)
C19—N3—C23	117.5 (3)	N2—C14—H14	118.9
C1—O1—Fe1	114.1 (2)	C15—C14—H14	118.9
C1—O1—H1	109.5	C14—C15—C16	119.4 (4)
Fe1—O1—H1	107.4	C14—C15—H15	120.3
C5—O2—Fe1	131.7 (2)	C16—C15—H15	120.3
O1—C1—C2	106.1 (3)	C17—C16—C15	118.5 (5)
O1—C1—H1A	110.5	C17—C16—H16	120.7
C2—C1—H1A	110.5	C15—C16—H16	120.7
O1—C1—H1B	110.5	C16—C17—C18	119.2 (5)
C2—C1—H1B	110.5	C16—C17—H17	120.4
H1A—C1—H1B	108.7	C18—C17—H17	120.4
N1—C2—C1	108.3 (3)	N2—C18—C17	122.9 (4)
N1—C2—H2A	110.0	N2—C18—H18	118.6
C1—C2—H2A	110.0	C17—C18—H18	118.6
N1—C2—H2B	110.0	N3—C19—C20	122.7 (5)
C1—C2—H2B	110.0	N3—C19—H19	118.7
H2A—C2—H2B	108.4	C20—C19—H19	118.7
N1—C3—C4	125.4 (3)	C21—C20—C19	118.3 (5)
N1—C3—H3	117.3	C21—C20—H20	120.8
C4—C3—H3	117.3	C19—C20—H20	120.8
C5—C4—C3	121.8 (3)	C20—C21—C22	119.1 (4)
C5—C4—C9	119.1 (3)	C20—C21—H21	120.5
C3—C4—C9	119.1 (3)	C22—C21—H21	120.5
O2—C5—C4	123.2 (3)	C21—C22—C23	119.8 (6)
O2—C5—C6	117.2 (3)	C21—C22—H22	120.1
C4—C5—C6	119.6 (3)	C23—C22—H22	120.1
C7—C6—C5	121.1 (4)	N3—C23—C22	122.6 (5)
C7—C6—H6	119.5	N3—C23—H23	118.7
C5—C6—H6	119.5	C22—C23—H23	118.7
C6—C7—C8	122.1 (4)

O2—Fe1—N1—C3	12.9 (3)	C3—C4—C5—O2	−4.1 (5)
O1—Fe1—N1—C3	−170.2 (3)	C9—C4—C5—O2	176.0 (3)
N2—Fe1—N1—C3	104.4 (3)	C3—C4—C5—C6	177.2 (3)
Cl1—Fe1—N1—C3	149.8 (3)	C9—C4—C5—C6	−2.8 (5)
Cl2—Fe1—N1—C3	−81.5 (3)	O2—C5—C6—C7	−179.5 (4)
O2—Fe1—N1—C2	−167.0 (3)	C4—C5—C6—C7	−0.7 (6)
O1—Fe1—N1—C2	9.8 (2)	C5—C6—C7—C8	1.7 (7)
N2—Fe1—N1—C2	−75.6 (3)	C6—C7—C8—C13	−178.5 (4)
Cl1—Fe1—N1—C2	−30.2 (5)	C6—C7—C8—C9	0.8 (7)
Cl2—Fe1—N1—C2	98.5 (3)	C7—C8—C9—C10	177.3 (4)
O2—Fe1—N2—C18	−146.3 (3)	C13—C8—C9—C10	−3.4 (5)
O1—Fe1—N2—C18	49.6 (3)	C7—C8—C9—C4	−4.2 (5)
N1—Fe1—N2—C18	127.5 (3)	C13—C8—C9—C4	175.1 (4)
Cl1—Fe1—N2—C18	−43.5 (3)	C5—C4—C9—C10	−176.5 (3)
O2—Fe1—N2—C14	34.9 (3)	C3—C4—C9—C10	3.6 (5)
O1—Fe1—N2—C14	−129.1 (3)	C5—C4—C9—C8	5.1 (5)
N1—Fe1—N2—C14	−51.3 (3)	C3—C4—C9—C8	−174.8 (3)
Cl1—Fe1—N2—C14	137.8 (3)	C8—C9—C10—C11	3.8 (6)
O2—Fe1—O1—C1	29.9 (5)	C4—C9—C10—C11	−174.6 (4)
N1—Fe1—O1—C1	19.0 (3)	C9—C10—C11—C12	−0.6 (7)
N2—Fe1—O1—C1	103.5 (3)	C10—C11—C12—C13	−3.2 (8)
Cl1—Fe1—O1—C1	−169.2 (3)	C11—C12—C13—C8	3.5 (8)
Cl2—Fe1—O1—C1	−71.3 (3)	C7—C8—C13—C12	179.1 (5)
O1—Fe1—O2—C5	−36.4 (6)	C9—C8—C13—C12	−0.2 (7)
N1—Fe1—O2—C5	−25.7 (3)	C18—N2—C14—C15	1.4 (6)
N2—Fe1—O2—C5	−109.0 (3)	Fe1—N2—C14—C15	−179.8 (3)
Cl1—Fe1—O2—C5	163.2 (3)	N2—C14—C15—C16	−0.3 (7)
Cl2—Fe1—O2—C5	64.0 (3)	C14—C15—C16—C17	−1.3 (8)
Fe1—O1—C1—C2	−42.2 (4)	C15—C16—C17—C18	1.8 (8)
C3—N1—C2—C1	145.1 (4)	C14—N2—C18—C17	−0.9 (6)
Fe1—N1—C2—C1	−34.9 (4)	Fe1—N2—C18—C17	−179.7 (3)
O1—C1—C2—N1	48.7 (5)	C16—C17—C18—N2	−0.7 (7)
C2—N1—C3—C4	179.1 (4)	C23—N3—C19—C20	0.5 (7)
Fe1—N1—C3—C4	−0.9 (5)	N3—C19—C20—C21	−0.3 (8)
N1—C3—C4—C5	−7.3 (6)	C19—C20—C21—C22	−0.8 (7)
N1—C3—C4—C9	172.6 (4)	C20—C21—C22—C23	1.7 (8)
Fe1—O2—C5—C4	25.9 (5)	C19—N3—C23—C22	0.3 (8)
Fe1—O2—C5—C6	−155.4 (3)	C21—C22—C23—N3	−1.5 (10)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3	0.82	1.81	2.617 (4)	168
C12—H12···Cgⁱ	0.93	2.71	3.594 (5)	159
C16—H16···Cgⁱⁱ	0.93	2.78	3.653 (6)	157

Symmetry codes: (i) −x, y−1/2, −z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[Fe(C₁₃H₁₂NO₂)Cl₂(C₅H₅N)]·C₅H₅N
M_r	499.19
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	7.8590 (6), 10.0153 (11), 14.4884 (16)
β (°)	90.123 (1)
V (Å³)	1140.4 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.92
Crystal size (mm)	0.48 × 0.44 × 0.37

Data collection
Diffractometer	Bruker SMART 1000 CCD
Absorption correction	Multi-scan (SADABS; Siemens, 1996)
T_min, T_max	0.666, 0.727
No. of measured, independent and observed [I > 2σ(I)] reflections	5726, 3395, 3143
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.085, 1.00
No. of reflections	3395
No. of parameters	281
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.19
Absolute structure	Flack (1983), 1265 Friedel pairs
Absolute structure parameter	0.02 (2)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3	0.82	1.81	2.617 (4)	168.0
C12—H12···Cgⁱ	0.93	2.71	3.594 (5)	159
C16—H16···Cgⁱⁱ	0.93	2.78	3.653 (6)	157

Symmetry codes: (i) −x, y−1/2, −z; (ii) x, y+1, z.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 20671048, 21041002)

References

Aromí, G. & Brechin, E. K. (2006). Struct. Bond. pp. 1–67. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Goodwin, J. C., Price, D. J., Powell, A. K. & Heath, S. L. (2000). Eur. J. Inorg. Chem. pp. 1407–1410. CrossRef Google Scholar
Hoshino, N., Ako, A. M., Powell, A. K. & Oshio, H. (2009). Inorg. Chem. 48, 3396–3407. Web of Science CSD CrossRef PubMed CAS Google Scholar
Oshio, H., Hoshino, N., Ito, T. & Nakano, M. (2004). J. Am. Chem. Soc. 126, 8805–8812. Web of Science CSD CrossRef PubMed CAS Google Scholar
Qian, J., Tian, J., Gu, W., Gao, S., Xin, L., Yan, S., Ribas, J., Liao, D. & Cheng, P. (2008). Dalton Trans. pp. 6948–6952. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART, SAINT and SADABS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­chlorido{1-[(2-hy­dr­oxy­eth­yl)imino­meth­yl]-2-naphtho­lato}pyridine­iron(III) pyridine monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Dichlorido{1-[(2-hydroxyethyl)iminomethyl]-2-naphtholato}pyridineiron(III) pyridine monosolvate