Dichlorido[1-(8-quinolylimino-meth-yl)-2-naphtholato]iron(III).

The Fe(III) ion in the title complex, [FeCl(2)(C(20)H(13)N(2)O)], has a distorted square-pyramidal coordination formed by one O atom and two N atoms from a tridentate 1-(8-quinolylimino-meth-yl)-2-naphtholate ligand and two Cl atoms. In the crystal structure, mol-ecules form a column structure along the a axis through π-π stacking inter-actions, with centroid-centroid distances of 3.657 (1) and 3.818 (2) Å. Weak C-H⋯Cl inter-actions are observed between the columns.

Related literature

For supra­molecular self-assembly, see: Crivillers & Furukawa (2009 ▶).

Experimental

Crystal data

[FeCl2(C20H13N2O)]

M = 424.07

Monoclinic,

a = 7.6177 (5) Å

b = 18.5256 (11) Å

c = 12.2073 (7) Å

β = 91.1612 (16)°

V = 1722.37 (18) Å3

Z = 4

Mo Kα radiation

μ = 1.20 mm−1

T = 293 K

0.80 × 0.20 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (; Higashi, 2001 ▶) T min = 0.448, T max = 0.890

17621 measured reflections

3934 independent reflections

3182 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.090

S = 1.08

3934 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.25 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalClear (Molecular Structure Corporation and 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/S1600536809022880/is2429sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022880/is2429Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[FeCl2(C20H13N2O)]	F(000) = 860
Mr = 424.07	Dx = 1.635 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 15565 reflections
a = 7.6177 (5) Å	θ = 3.1–27.7°
b = 18.5256 (11) Å	µ = 1.20 mm−1
c = 12.2073 (7) Å	T = 293 K
β = 91.1612 (16)°	Needle, black
V = 1722.37 (18) Å3	0.80 × 0.20 × 0.10 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	3934 independent reflections
Radiation source: fine-focus sealed tube	3182 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 2001)	h = −9→9
Tmin = 0.448, Tmax = 0.890	k = −24→23
17621 measured reflections	l = −15→15

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0395P)2 + 0.7323P] where P = (Fo2 + 2Fc2)/3
3934 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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
Fe1	0.16122 (4)	0.072865 (16)	0.67792 (2)	0.03433 (11)
C1	0.1279 (3)	−0.04180 (15)	0.8607 (2)	0.0498 (6)
H1	0.0834	−0.0042	0.9022	0.060*
C2	0.1519 (4)	−0.10907 (17)	0.9103 (2)	0.0599 (7)
H2	0.1216	−0.1161	0.9830	0.072*
C3	0.2195 (4)	−0.16364 (16)	0.8515 (2)	0.0562 (7)
H3	0.2361	−0.2086	0.8839	0.067*
C4	0.2653 (3)	−0.15321 (13)	0.74142 (19)	0.0409 (5)
C5	0.3412 (3)	−0.20622 (12)	0.6755 (2)	0.0485 (6)
H4	0.3632	−0.2521	0.7035	0.058*
C6	0.3825 (3)	−0.19030 (12)	0.5702 (2)	0.0451 (6)
H5	0.4356	−0.2254	0.5276	0.054*
C7	0.3470 (3)	−0.12257 (12)	0.52462 (19)	0.0401 (5)
H6	0.3743	−0.1136	0.4520	0.048*
C8	0.2723 (3)	−0.06922 (10)	0.58598 (17)	0.0306 (4)
C9	0.2340 (3)	−0.08413 (11)	0.69642 (17)	0.0329 (4)
C10	0.2480 (3)	0.01983 (11)	0.44882 (17)	0.0321 (4)
H7	0.2835	−0.0167	0.4020	0.038*
C11	0.2188 (3)	0.08832 (11)	0.40091 (17)	0.0327 (4)
C12	0.1502 (3)	0.14570 (12)	0.46229 (19)	0.0399 (5)
C13	0.1253 (3)	0.21425 (13)	0.4125 (2)	0.0495 (6)
H13	0.0767	0.2516	0.4526	0.059*
C14	0.1709 (3)	0.22598 (14)	0.3084 (2)	0.0524 (7)
H12	0.1570	0.2719	0.2789	0.063*
C15	0.2392 (3)	0.17054 (13)	0.24256 (19)	0.0441 (6)
C16	0.2835 (4)	0.18369 (17)	0.1329 (2)	0.0600 (8)
H11	0.2733	0.2303	0.1052	0.072*
C17	0.3403 (4)	0.13057 (19)	0.0673 (2)	0.0655 (8)
H10	0.3656	0.1400	−0.0055	0.079*
C18	0.3606 (4)	0.06130 (17)	0.1099 (2)	0.0586 (7)
H9	0.3989	0.0244	0.0647	0.070*
C19	0.3254 (3)	0.04645 (14)	0.21726 (19)	0.0450 (6)
H8	0.3441	0.0001	0.2444	0.054*
C20	0.2612 (3)	0.10040 (12)	0.28673 (18)	0.0354 (5)
N1	0.1657 (2)	−0.02918 (10)	0.75694 (14)	0.0366 (4)
N2	0.2306 (2)	0.00218 (9)	0.55195 (14)	0.0305 (4)
O1	0.1072 (3)	0.13872 (9)	0.56416 (14)	0.0559 (5)
Cl1	0.40989 (8)	0.11675 (4)	0.74667 (6)	0.05373 (18)
Cl2	−0.06535 (9)	0.11031 (4)	0.77771 (7)	0.0629 (2)

	U11	U22	U33	U12	U13	U23
Fe1	0.03643 (18)	0.03247 (18)	0.03430 (17)	0.00072 (13)	0.00555 (13)	−0.00741 (13)
C1	0.0496 (15)	0.0636 (17)	0.0365 (12)	−0.0030 (13)	0.0074 (11)	0.0006 (12)
C2	0.0656 (18)	0.076 (2)	0.0387 (14)	−0.0091 (16)	0.0045 (13)	0.0150 (14)
C3	0.0592 (17)	0.0552 (16)	0.0539 (15)	−0.0136 (13)	−0.0071 (13)	0.0222 (13)
C4	0.0372 (12)	0.0376 (12)	0.0476 (13)	−0.0079 (10)	−0.0082 (10)	0.0090 (10)
C5	0.0510 (15)	0.0290 (12)	0.0650 (16)	−0.0031 (11)	−0.0136 (13)	0.0054 (11)
C6	0.0474 (14)	0.0306 (11)	0.0569 (15)	0.0025 (10)	−0.0076 (12)	−0.0099 (10)
C7	0.0459 (13)	0.0345 (12)	0.0400 (12)	0.0007 (10)	0.0006 (10)	−0.0067 (9)
C8	0.0299 (10)	0.0264 (10)	0.0354 (11)	−0.0023 (8)	−0.0013 (8)	−0.0019 (8)
C9	0.0282 (10)	0.0336 (11)	0.0367 (11)	−0.0055 (9)	−0.0026 (8)	0.0006 (9)
C10	0.0328 (11)	0.0313 (11)	0.0322 (10)	0.0007 (9)	0.0034 (8)	−0.0047 (8)
C11	0.0314 (11)	0.0317 (11)	0.0348 (11)	−0.0002 (9)	−0.0015 (9)	−0.0010 (8)
C12	0.0397 (12)	0.0377 (12)	0.0420 (12)	0.0075 (10)	−0.0076 (10)	−0.0035 (10)
C13	0.0530 (15)	0.0365 (13)	0.0583 (16)	0.0138 (11)	−0.0138 (12)	−0.0061 (11)
C14	0.0528 (16)	0.0383 (13)	0.0654 (18)	0.0043 (11)	−0.0165 (13)	0.0139 (12)
C15	0.0390 (13)	0.0461 (14)	0.0466 (13)	−0.0034 (11)	−0.0099 (10)	0.0126 (11)
C16	0.0582 (17)	0.0689 (19)	0.0525 (16)	−0.0071 (15)	−0.0085 (14)	0.0291 (14)
C17	0.0636 (19)	0.092 (2)	0.0408 (14)	−0.0143 (17)	0.0042 (13)	0.0187 (15)
C18	0.0532 (16)	0.080 (2)	0.0431 (14)	−0.0083 (14)	0.0114 (12)	−0.0013 (14)
C19	0.0465 (14)	0.0495 (14)	0.0391 (12)	−0.0061 (11)	0.0077 (11)	0.0021 (11)
C20	0.0307 (11)	0.0381 (11)	0.0372 (11)	−0.0044 (9)	−0.0033 (9)	0.0049 (9)
N1	0.0371 (10)	0.0410 (10)	0.0317 (9)	−0.0036 (8)	0.0040 (8)	−0.0004 (8)
N2	0.0339 (9)	0.0276 (8)	0.0301 (9)	0.0004 (7)	0.0020 (7)	−0.0019 (7)
O1	0.0798 (13)	0.0474 (10)	0.0406 (9)	0.0282 (9)	0.0024 (9)	−0.0061 (8)
Cl1	0.0437 (3)	0.0501 (4)	0.0674 (4)	−0.0116 (3)	0.0018 (3)	−0.0121 (3)
Cl2	0.0552 (4)	0.0489 (4)	0.0858 (5)	0.0031 (3)	0.0354 (4)	−0.0098 (3)

Fe1—O1	1.8876 (17)	C9—N1	1.367 (3)
Fe1—N2	2.0957 (17)	C10—C11	1.413 (3)
Fe1—N1	2.1223 (19)	C10—N2	1.310 (3)
Fe1—Cl1	2.2111 (7)	C10—H7	0.9300
Fe1—Cl2	2.2426 (7)	C11—C12	1.407 (3)
C1—C2	1.396 (4)	C11—C20	1.454 (3)
C1—N1	1.325 (3)	C12—C13	1.419 (3)
C1—H1	0.9300	C12—O1	1.299 (3)
C2—C3	1.349 (4)	C13—C14	1.342 (4)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.408 (3)	C14—C15	1.410 (4)
C3—H3	0.9300	C14—H12	0.9300
C4—C5	1.402 (3)	C15—C16	1.408 (4)
C4—C9	1.411 (3)	C15—C20	1.416 (3)
C5—C6	1.362 (4)	C16—C17	1.346 (4)
C5—H4	0.9300	C16—H11	0.9300
C6—H5	0.9300	C17—H10	0.9300
C6—C7	1.397 (3)	C18—C17	1.392 (4)
C7—C8	1.371 (3)	C18—H9	0.9300
C7—H6	0.9300	C19—C18	1.371 (3)
C8—C9	1.412 (3)	C19—H8	0.9300
C8—N2	1.420 (3)	C20—C19	1.405 (3)
Fe1—N1—C1	126.14 (17)	C11—C20—C15	118.6 (2)
Fe1—N1—C9	114.86 (14)	C11—C20—C19	123.8 (2)
Fe1—N2—C8	115.18 (13)	C12—C11—C20	119.1 (2)
Fe1—N2—C10	125.53 (14)	C12—C13—H13	119.5
Fe1—O1—C12	135.52 (15)	C13—C12—O1	117.7 (2)
C1—C2—C3	119.1 (2)	C13—C14—C15	121.8 (2)
C1—C2—H2	120.5	C13—C14—H12	119.1
C1—N1—C9	118.5 (2)	C14—C13—C12	121.1 (2)
C2—C1—N1	122.9 (3)	C14—C13—H13	119.5
C2—C1—H1	118.5	C14—C15—C20	119.6 (2)
C2—C3—C4	120.7 (2)	C15—C14—H12	119.1
C2—C3—H3	119.7	C15—C16—H11	119.2
C3—C2—H2	120.5	C15—C20—C19	117.6 (2)
C3—C4—C5	124.4 (2)	C16—C15—C14	120.9 (2)
C3—C4—C9	116.9 (2)	C16—C15—C20	119.5 (2)
C4—C3—H3	119.7	C16—C17—C18	119.1 (3)
C4—C5—C6	119.8 (2)	C16—C17—H10	120.4
C4—C5—H4	120.1	C17—C16—C15	121.7 (3)
C4—C9—C8	120.8 (2)	C17—C16—H11	119.2
C4—C9—N1	121.9 (2)	C17—C18—C19	121.3 (3)
C5—C4—C9	118.7 (2)	C17—C18—H9	119.3
C5—C6—C7	121.6 (2)	C18—C17—H10	120.4
C5—C6—H5	119.2	C18—C19—C20	120.8 (3)
C6—C5—H4	120.1	C18—C19—H8	119.6
C6—C7—C8	120.6 (2)	C19—C18—H9	119.3
C6—C7—H6	119.7	C20—C19—H8	119.6
C7—C6—H5	119.2	N1—Fe1—N2	77.00 (7)
C7—C8—C9	118.47 (19)	N1—Fe1—O1	155.70 (8)
C7—C8—N2	127.17 (19)	N1—Fe1—Cl1	98.59 (5)
C8—C7—H6	119.7	N1—Fe1—Cl2	91.95 (5)
C8—C9—N1	117.29 (19)	N1—C1—H1	118.5
C8—N2—C10	119.16 (17)	N2—Fe1—O1	85.32 (7)
C9—C8—N2	114.34 (18)	N2—Fe1—Cl1	106.34 (5)
C10—C11—C12	121.0 (2)	N2—Fe1—Cl2	143.16 (5)
C10—C11—C20	119.91 (19)	N2—C10—H7	116.4
C11—C10—N2	127.14 (19)	O1—Fe1—Cl1	102.35 (7)
C11—C10—H7	116.4	O1—Fe1—Cl2	92.36 (6)
C11—C12—C13	119.7 (2)	Cl1—Fe1—Cl2	110.06 (3)
C11—C12—O1	122.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H12···Cl1i	0.93	2.81	3.598 (2)	143
C19—H8···Cl1ii	0.93	2.86	3.656 (2)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H12⋯Cl1i	0.93	2.81	3.598 (2)	143
C19—H8⋯Cl1ii	0.93	2.86	3.656 (2)	144

Symmetry codes: (i) ; (ii) .