metal-organic compounds
[2,6-Bis(6-methylquinolin-2-yl)pyridine-κ3N,N′,N′′]dichloridoiron(II)
aDepartment of Chemistry, Shaanxi Key Laboratory for Physico-Inorganic Chemistry, Northwest University, Xi'an 710069, People's Republic of China, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
In the molecule of the title compound, [FeCl2(C25H19N3)], the three N atoms span the axial–equatorial–axial sites of the trigonal-bipyramidal the geometry of the FeII atom is 32% distorted from trigonal-bipyramidal (towards square-pyramidal along the pathway). One of the Cl atoms is disordered over two positions in a 0.938 (11):0.062 (11) ratio. Intermolecular C—H⋯Cl hydrogen bonding occurs in the crystal structure.
Related literature
For the synthesis of the N-heterocyclic ligand, see: Buu-Hoi et al. (1965). For a related structure, see: Li et al. (2010).
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536810037049/xu5032sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536810037049/xu5032Isup2.hkl
The ligand was synthesized by using a literature procedure (Buu-Hoi et al., 1965).
Bis[2'-(6-methylquinolinyl)]pyridine (0.018 g, 0.05 mmol), and ferrous chloride tetrahydrate (0.02 g, 0.05 mmol) along with five drops of 1 M hydrochloric acid were dissolved in ethanol (10 ml). The mixture was heated in a Teflon-lined, stainless-steel Parr bomb at 363 K for 120 h. The bomb was cooled at 5 K per hour. Black crystals were isolated.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.95–0.98 Å) and were included in the
in the riding model approximation, with U(H) set to 1.2–1.5U(C).One of the chlorine atoms is disordered over two positions in a 0.938 (11):0.062 (11) ratio. The Fe–Cl pair of distances were restrained to within 0.01 Å of each other; the anisotropic temperature factors of the minor component were restrained to be nearly isotropic.
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of FeCl2(C25H19N3) at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown. |
[FeCl2(C25H19N3)] | Z = 2 |
Mr = 488.18 | F(000) = 500 |
Triclinic, P1 | Dx = 1.552 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6228 (7) Å | Cell parameters from 4559 reflections |
b = 10.2558 (8) Å | θ = 2.6–28.2° |
c = 10.7324 (8) Å | µ = 1.00 mm−1 |
α = 94.352 (1)° | T = 100 K |
β = 95.481 (1)° | Block, black |
γ = 96.121 (1)° | 0.30 × 0.10 × 0.05 mm |
V = 1044.35 (14) Å3 |
Bruker SMART APEX diffractometer | 4757 independent reflections |
Radiation source: fine-focus sealed tube | 3954 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ω scans | θmax = 27.5°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.754, Tmax = 0.952 | k = −13→13 |
9910 measured reflections | l = −13→13 |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0511P)2 + 1.0201P] where P = (Fo2 + 2Fc2)/3 |
4757 reflections | (Δ/σ)max = 0.001 |
292 parameters | Δρmax = 0.54 e Å−3 |
7 restraints | Δρmin = −0.44 e Å−3 |
[FeCl2(C25H19N3)] | γ = 96.121 (1)° |
Mr = 488.18 | V = 1044.35 (14) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.6228 (7) Å | Mo Kα radiation |
b = 10.2558 (8) Å | µ = 1.00 mm−1 |
c = 10.7324 (8) Å | T = 100 K |
α = 94.352 (1)° | 0.30 × 0.10 × 0.05 mm |
β = 95.481 (1)° |
Bruker SMART APEX diffractometer | 4757 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3954 reflections with I > 2σ(I) |
Tmin = 0.754, Tmax = 0.952 | Rint = 0.024 |
9910 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 7 restraints |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.54 e Å−3 |
4757 reflections | Δρmin = −0.44 e Å−3 |
292 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Fe1 | 0.34748 (3) | 0.81412 (3) | 0.22283 (3) | 0.01918 (11) | |
Cl1 | 0.16748 (18) | 0.73795 (9) | 0.34366 (18) | 0.0225 (4) | 0.938 (11) |
Cl1' | 0.211 (5) | 0.730 (2) | 0.377 (3) | 0.047 (6) | 0.062 (11) |
Cl2 | 0.27672 (8) | 0.85227 (6) | 0.02182 (6) | 0.03212 (17) | |
N1 | 0.4298 (2) | 0.61956 (18) | 0.19090 (18) | 0.0185 (4) | |
N2 | 0.5602 (2) | 0.84553 (19) | 0.29589 (18) | 0.0188 (4) | |
N3 | 0.3828 (2) | 1.02324 (19) | 0.31020 (18) | 0.0185 (4) | |
C1 | 0.3563 (2) | 0.5061 (2) | 0.1319 (2) | 0.0197 (5) | |
C2 | 0.2114 (3) | 0.5039 (2) | 0.0943 (2) | 0.0236 (5) | |
H2 | 0.1656 | 0.5803 | 0.1097 | 0.028* | |
C3 | 0.1373 (3) | 0.3912 (2) | 0.0355 (2) | 0.0233 (5) | |
H3 | 0.0398 | 0.3910 | 0.0107 | 0.028* | |
C4 | 0.2005 (3) | 0.2747 (2) | 0.0101 (2) | 0.0214 (5) | |
C5 | 0.3407 (3) | 0.2756 (2) | 0.0458 (2) | 0.0218 (5) | |
H5 | 0.3846 | 0.1984 | 0.0289 | 0.026* | |
C6 | 0.4219 (3) | 0.3901 (2) | 0.1079 (2) | 0.0201 (5) | |
C7 | 0.1113 (3) | 0.1550 (2) | −0.0542 (2) | 0.0268 (5) | |
H7A | 0.1709 | 0.0855 | −0.0718 | 0.040* | |
H7B | 0.0637 | 0.1775 | −0.1333 | 0.040* | |
H7C | 0.0411 | 0.1239 | 0.0004 | 0.040* | |
C8 | 0.5659 (3) | 0.3955 (2) | 0.1470 (2) | 0.0251 (5) | |
H8 | 0.6136 | 0.3202 | 0.1327 | 0.030* | |
C9 | 0.6372 (3) | 0.5093 (3) | 0.2057 (2) | 0.0255 (5) | |
H9 | 0.7346 | 0.5133 | 0.2328 | 0.031* | |
C10 | 0.5660 (2) | 0.6202 (2) | 0.2256 (2) | 0.0187 (5) | |
C11 | 0.6408 (2) | 0.7465 (2) | 0.2875 (2) | 0.0183 (5) | |
C12 | 0.7816 (2) | 0.7639 (2) | 0.3330 (2) | 0.0209 (5) | |
H12 | 0.8377 | 0.6935 | 0.3254 | 0.025* | |
C13 | 0.8396 (3) | 0.8867 (2) | 0.3902 (2) | 0.0228 (5) | |
H13 | 0.9361 | 0.9009 | 0.4218 | 0.027* | |
C14 | 0.7556 (3) | 0.9881 (2) | 0.4005 (2) | 0.0224 (5) | |
H14 | 0.7932 | 1.0722 | 0.4401 | 0.027* | |
C15 | 0.6156 (2) | 0.9643 (2) | 0.3520 (2) | 0.0197 (5) | |
C16 | 0.5151 (3) | 1.0641 (2) | 0.3564 (2) | 0.0203 (5) | |
C17 | 0.5577 (3) | 1.1949 (3) | 0.4088 (3) | 0.0285 (6) | |
H17 | 0.6527 | 1.2214 | 0.4412 | 0.034* | |
C18 | 0.4599 (3) | 1.2824 (3) | 0.4121 (2) | 0.0281 (6) | |
H18 | 0.4876 | 1.3704 | 0.4466 | 0.034* | |
C19 | 0.3201 (3) | 1.2440 (2) | 0.3654 (2) | 0.0211 (5) | |
C20 | 0.2134 (3) | 1.3296 (2) | 0.3667 (2) | 0.0238 (5) | |
H20 | 0.2370 | 1.4186 | 0.3999 | 0.029* | |
C21 | 0.0778 (3) | 1.2866 (2) | 0.3213 (2) | 0.0259 (5) | |
C22 | 0.0444 (3) | 1.1538 (2) | 0.2698 (2) | 0.0249 (5) | |
H22 | −0.0495 | 1.1237 | 0.2364 | 0.030* | |
C23 | 0.1446 (3) | 1.0680 (2) | 0.2674 (2) | 0.0223 (5) | |
H23 | 0.1192 | 0.9793 | 0.2339 | 0.027* | |
C24 | 0.2846 (3) | 1.1113 (2) | 0.3143 (2) | 0.0199 (5) | |
C25 | −0.0365 (3) | 1.3765 (3) | 0.3212 (3) | 0.0342 (6) | |
H25A | 0.0059 | 1.4683 | 0.3288 | 0.051* | |
H25B | −0.0911 | 1.3611 | 0.3923 | 0.051* | |
H25C | −0.0985 | 1.3583 | 0.2425 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.01616 (18) | 0.01714 (17) | 0.02359 (19) | 0.00279 (12) | 0.00055 (13) | −0.00168 (13) |
Cl1 | 0.0196 (5) | 0.0208 (4) | 0.0263 (6) | −0.0002 (3) | 0.0040 (4) | −0.0017 (3) |
Cl1' | 0.046 (10) | 0.052 (8) | 0.042 (9) | −0.001 (7) | 0.013 (8) | −0.005 (6) |
Cl2 | 0.0433 (4) | 0.0305 (3) | 0.0245 (3) | 0.0176 (3) | 0.0004 (3) | −0.0001 (2) |
N1 | 0.0183 (10) | 0.0174 (9) | 0.0195 (10) | 0.0013 (7) | 0.0009 (8) | 0.0012 (7) |
N2 | 0.0170 (9) | 0.0187 (9) | 0.0206 (10) | 0.0006 (7) | 0.0048 (8) | 0.0005 (7) |
N3 | 0.0173 (10) | 0.0197 (9) | 0.0182 (9) | 0.0014 (8) | 0.0023 (7) | 0.0001 (7) |
C1 | 0.0218 (12) | 0.0175 (10) | 0.0200 (11) | 0.0019 (9) | 0.0032 (9) | 0.0014 (9) |
C2 | 0.0221 (12) | 0.0200 (11) | 0.0279 (13) | 0.0032 (9) | 0.0000 (10) | −0.0021 (9) |
C3 | 0.0191 (12) | 0.0218 (11) | 0.0279 (13) | 0.0002 (9) | 0.0005 (10) | 0.0012 (10) |
C4 | 0.0274 (13) | 0.0191 (11) | 0.0171 (11) | 0.0009 (9) | 0.0009 (9) | 0.0014 (9) |
C5 | 0.0275 (13) | 0.0181 (11) | 0.0203 (12) | 0.0049 (9) | 0.0032 (10) | 0.0005 (9) |
C6 | 0.0242 (12) | 0.0185 (11) | 0.0187 (11) | 0.0037 (9) | 0.0049 (9) | 0.0040 (9) |
C7 | 0.0339 (14) | 0.0191 (11) | 0.0255 (13) | −0.0015 (10) | 0.0006 (11) | −0.0012 (9) |
C8 | 0.0268 (13) | 0.0236 (12) | 0.0263 (13) | 0.0073 (10) | 0.0046 (10) | 0.0019 (10) |
C9 | 0.0214 (12) | 0.0284 (13) | 0.0276 (13) | 0.0068 (10) | 0.0025 (10) | 0.0022 (10) |
C10 | 0.0202 (11) | 0.0186 (11) | 0.0178 (11) | 0.0028 (9) | 0.0035 (9) | 0.0032 (9) |
C11 | 0.0186 (11) | 0.0206 (11) | 0.0154 (11) | 0.0007 (9) | 0.0036 (9) | 0.0006 (9) |
C12 | 0.0182 (11) | 0.0263 (12) | 0.0183 (11) | 0.0036 (9) | 0.0014 (9) | 0.0016 (9) |
C13 | 0.0177 (11) | 0.0302 (12) | 0.0202 (12) | 0.0010 (10) | 0.0029 (9) | 0.0022 (10) |
C14 | 0.0222 (12) | 0.0228 (11) | 0.0208 (12) | −0.0021 (9) | 0.0030 (9) | −0.0016 (9) |
C15 | 0.0210 (12) | 0.0206 (11) | 0.0181 (11) | 0.0030 (9) | 0.0046 (9) | 0.0006 (9) |
C16 | 0.0229 (12) | 0.0201 (11) | 0.0189 (11) | 0.0026 (9) | 0.0065 (9) | 0.0023 (9) |
C17 | 0.0276 (13) | 0.0292 (13) | 0.0274 (13) | 0.0009 (11) | 0.0000 (11) | 0.0007 (10) |
C18 | 0.0343 (15) | 0.0222 (12) | 0.0273 (13) | −0.0010 (11) | 0.0056 (11) | 0.0012 (10) |
C19 | 0.0256 (12) | 0.0192 (11) | 0.0187 (11) | 0.0009 (9) | 0.0054 (9) | 0.0012 (9) |
C20 | 0.0309 (13) | 0.0181 (11) | 0.0232 (12) | 0.0039 (10) | 0.0076 (10) | 0.0003 (9) |
C21 | 0.0285 (13) | 0.0242 (12) | 0.0281 (13) | 0.0085 (10) | 0.0100 (10) | 0.0063 (10) |
C22 | 0.0227 (12) | 0.0248 (12) | 0.0285 (13) | 0.0036 (10) | 0.0066 (10) | 0.0056 (10) |
C23 | 0.0241 (12) | 0.0192 (11) | 0.0242 (12) | 0.0029 (9) | 0.0053 (10) | 0.0010 (9) |
C24 | 0.0230 (12) | 0.0187 (11) | 0.0196 (11) | 0.0039 (9) | 0.0071 (9) | 0.0028 (9) |
C25 | 0.0296 (14) | 0.0257 (13) | 0.0502 (18) | 0.0101 (11) | 0.0092 (13) | 0.0059 (12) |
Fe1—N1 | 2.2386 (19) | C9—H9 | 0.9500 |
Fe1—N2 | 2.103 (2) | C10—C11 | 1.488 (3) |
Fe1—N3 | 2.2523 (19) | C11—C12 | 1.384 (3) |
Fe1—Cl1 | 2.3636 (8) | C12—C13 | 1.393 (3) |
Fe1—Cl1' | 2.369 (9) | C12—H12 | 0.9500 |
Fe1—Cl2 | 2.2748 (7) | C13—C14 | 1.388 (3) |
N1—C10 | 1.328 (3) | C13—H13 | 0.9500 |
N1—C1 | 1.372 (3) | C14—C15 | 1.386 (3) |
N2—C11 | 1.345 (3) | C14—H14 | 0.9500 |
N2—C15 | 1.349 (3) | C15—C16 | 1.483 (3) |
N3—C16 | 1.333 (3) | C16—C17 | 1.416 (3) |
N3—C24 | 1.376 (3) | C17—C18 | 1.369 (4) |
C1—C2 | 1.411 (3) | C17—H17 | 0.9500 |
C1—C6 | 1.423 (3) | C18—C19 | 1.394 (4) |
C2—C3 | 1.368 (3) | C18—H18 | 0.9500 |
C2—H2 | 0.9500 | C19—C24 | 1.422 (3) |
C3—C4 | 1.418 (3) | C19—C20 | 1.420 (3) |
C3—H3 | 0.9500 | C20—C21 | 1.363 (4) |
C4—C5 | 1.365 (3) | C20—H20 | 0.9500 |
C4—C7 | 1.501 (3) | C21—C22 | 1.422 (4) |
C5—C6 | 1.421 (3) | C21—C25 | 1.508 (3) |
C5—H5 | 0.9500 | C22—C23 | 1.373 (3) |
C6—C8 | 1.403 (3) | C22—H22 | 0.9500 |
C7—H7A | 0.9800 | C23—C24 | 1.406 (3) |
C7—H7B | 0.9800 | C23—H23 | 0.9500 |
C7—H7C | 0.9800 | C25—H25A | 0.9800 |
C8—C9 | 1.365 (4) | C25—H25B | 0.9800 |
C8—H8 | 0.9500 | C25—H25C | 0.9800 |
C9—C10 | 1.402 (3) | ||
N2—Fe1—N1 | 74.57 (7) | C10—C9—H9 | 120.2 |
N2—Fe1—N3 | 74.29 (7) | N1—C10—C9 | 122.6 (2) |
N1—Fe1—N3 | 148.58 (7) | N1—C10—C11 | 116.18 (19) |
N2—Fe1—Cl2 | 121.77 (6) | C9—C10—C11 | 121.2 (2) |
N1—Fe1—Cl2 | 100.57 (5) | N2—C11—C12 | 121.4 (2) |
N3—Fe1—Cl2 | 99.20 (5) | N2—C11—C10 | 114.5 (2) |
N2—Fe1—Cl1 | 122.35 (8) | C12—C11—C10 | 124.1 (2) |
N1—Fe1—Cl1 | 95.84 (6) | C11—C12—C13 | 118.8 (2) |
N3—Fe1—Cl1 | 97.19 (6) | C11—C12—H12 | 120.6 |
Cl2—Fe1—Cl1 | 115.88 (6) | C13—C12—H12 | 120.6 |
N2—Fe1—Cl1' | 109.4 (15) | C14—C13—C12 | 119.6 (2) |
N1—Fe1—Cl1' | 90.5 (9) | C14—C13—H13 | 120.2 |
N3—Fe1—Cl1' | 95.9 (5) | C12—C13—H13 | 120.2 |
Cl2—Fe1—Cl1' | 128.8 (15) | C15—C14—C13 | 118.6 (2) |
Cl1—Fe1—Cl1' | 13.1 (14) | C15—C14—H14 | 120.7 |
C10—N1—C1 | 118.53 (19) | C13—C14—H14 | 120.7 |
C10—N1—Fe1 | 114.81 (15) | N2—C15—C14 | 121.5 (2) |
C1—N1—Fe1 | 126.46 (15) | N2—C15—C16 | 114.5 (2) |
C11—N2—C15 | 120.0 (2) | C14—C15—C16 | 124.0 (2) |
C11—N2—Fe1 | 119.82 (16) | N3—C16—C17 | 122.2 (2) |
C15—N2—Fe1 | 120.19 (15) | N3—C16—C15 | 116.2 (2) |
C16—N3—C24 | 118.6 (2) | C17—C16—C15 | 121.5 (2) |
C16—N3—Fe1 | 114.61 (15) | C18—C17—C16 | 119.0 (2) |
C24—N3—Fe1 | 126.69 (15) | C18—C17—H17 | 120.5 |
N1—C1—C2 | 119.2 (2) | C16—C17—H17 | 120.5 |
N1—C1—C6 | 121.8 (2) | C17—C18—C19 | 120.9 (2) |
C2—C1—C6 | 119.0 (2) | C17—C18—H18 | 119.6 |
C3—C2—C1 | 119.6 (2) | C19—C18—H18 | 119.6 |
C3—C2—H2 | 120.2 | C18—C19—C24 | 117.1 (2) |
C1—C2—H2 | 120.2 | C18—C19—C20 | 123.7 (2) |
C2—C3—C4 | 122.5 (2) | C24—C19—C20 | 119.2 (2) |
C2—C3—H3 | 118.8 | C21—C20—C19 | 121.3 (2) |
C4—C3—H3 | 118.8 | C21—C20—H20 | 119.3 |
C5—C4—C3 | 118.5 (2) | C19—C20—H20 | 119.3 |
C5—C4—C7 | 122.5 (2) | C20—C21—C22 | 118.7 (2) |
C3—C4—C7 | 119.0 (2) | C20—C21—C25 | 122.0 (2) |
C4—C5—C6 | 121.1 (2) | C22—C21—C25 | 119.3 (2) |
C4—C5—H5 | 119.4 | C23—C22—C21 | 121.6 (2) |
C6—C5—H5 | 119.4 | C23—C22—H22 | 119.2 |
C8—C6—C5 | 123.2 (2) | C21—C22—H22 | 119.2 |
C8—C6—C1 | 117.5 (2) | C22—C23—C24 | 120.1 (2) |
C5—C6—C1 | 119.4 (2) | C22—C23—H23 | 120.0 |
C4—C7—H7A | 109.5 | C24—C23—H23 | 120.0 |
C4—C7—H7B | 109.5 | N3—C24—C23 | 118.8 (2) |
H7A—C7—H7B | 109.5 | N3—C24—C19 | 122.2 (2) |
C4—C7—H7C | 109.5 | C23—C24—C19 | 119.0 (2) |
H7A—C7—H7C | 109.5 | C21—C25—H25A | 109.5 |
H7B—C7—H7C | 109.5 | C21—C25—H25B | 109.5 |
C9—C8—C6 | 119.8 (2) | H25A—C25—H25B | 109.5 |
C9—C8—H8 | 120.1 | C21—C25—H25C | 109.5 |
C6—C8—H8 | 120.1 | H25A—C25—H25C | 109.5 |
C8—C9—C10 | 119.7 (2) | H25B—C25—H25C | 109.5 |
C8—C9—H9 | 120.2 | ||
N2—Fe1—N1—C10 | −3.07 (16) | C1—N1—C10—C11 | 179.1 (2) |
N3—Fe1—N1—C10 | −10.9 (2) | Fe1—N1—C10—C11 | 3.8 (3) |
Cl2—Fe1—N1—C10 | 117.20 (16) | C8—C9—C10—N1 | 0.8 (4) |
Cl1—Fe1—N1—C10 | −125.06 (17) | C8—C9—C10—C11 | −179.1 (2) |
Cl1'—Fe1—N1—C10 | −113.1 (13) | C15—N2—C11—C12 | −1.4 (3) |
N2—Fe1—N1—C1 | −177.9 (2) | Fe1—N2—C11—C12 | 179.14 (17) |
N3—Fe1—N1—C1 | 174.20 (17) | C15—N2—C11—C10 | 178.9 (2) |
Cl2—Fe1—N1—C1 | −57.66 (19) | Fe1—N2—C11—C10 | −0.5 (3) |
Cl1—Fe1—N1—C1 | 60.08 (19) | N1—C10—C11—N2 | −2.3 (3) |
Cl1'—Fe1—N1—C1 | 72.0 (13) | C9—C10—C11—N2 | 177.5 (2) |
N1—Fe1—N2—C11 | 1.86 (17) | N1—C10—C11—C12 | 178.0 (2) |
N3—Fe1—N2—C11 | 177.61 (19) | C9—C10—C11—C12 | −2.1 (4) |
Cl2—Fe1—N2—C11 | −91.17 (17) | N2—C11—C12—C13 | 0.9 (3) |
Cl1—Fe1—N2—C11 | 89.00 (17) | C10—C11—C12—C13 | −179.5 (2) |
Cl1'—Fe1—N2—C11 | 86.8 (7) | C11—C12—C13—C14 | 0.2 (4) |
N1—Fe1—N2—C15 | −177.57 (19) | C12—C13—C14—C15 | −0.7 (4) |
N3—Fe1—N2—C15 | −1.81 (17) | C11—N2—C15—C14 | 0.9 (3) |
Cl2—Fe1—N2—C15 | 89.40 (18) | Fe1—N2—C15—C14 | −179.70 (18) |
Cl1—Fe1—N2—C15 | −90.42 (18) | C11—N2—C15—C16 | −179.2 (2) |
Cl1'—Fe1—N2—C15 | −92.6 (7) | Fe1—N2—C15—C16 | 0.2 (3) |
N2—Fe1—N3—C16 | 3.33 (16) | C13—C14—C15—N2 | 0.2 (4) |
N1—Fe1—N3—C16 | 11.2 (2) | C13—C14—C15—C16 | −179.7 (2) |
Cl2—Fe1—N3—C16 | −117.23 (16) | C24—N3—C16—C17 | −0.3 (3) |
Cl1—Fe1—N3—C16 | 124.98 (17) | Fe1—N3—C16—C17 | 176.64 (19) |
Cl1'—Fe1—N3—C16 | 111.9 (15) | C24—N3—C16—C15 | 178.7 (2) |
N2—Fe1—N3—C24 | −180.0 (2) | Fe1—N3—C16—C15 | −4.3 (3) |
N1—Fe1—N3—C24 | −172.12 (17) | N2—C15—C16—N3 | 2.9 (3) |
Cl2—Fe1—N3—C24 | 59.44 (19) | C14—C15—C16—N3 | −177.2 (2) |
Cl1—Fe1—N3—C24 | −58.34 (19) | N2—C15—C16—C17 | −178.1 (2) |
Cl1'—Fe1—N3—C24 | −71.4 (15) | C14—C15—C16—C17 | 1.8 (4) |
C10—N1—C1—C2 | −180.0 (2) | N3—C16—C17—C18 | −0.1 (4) |
Fe1—N1—C1—C2 | −5.3 (3) | C15—C16—C17—C18 | −179.0 (2) |
C10—N1—C1—C6 | 0.4 (3) | C16—C17—C18—C19 | 0.4 (4) |
Fe1—N1—C1—C6 | 175.07 (17) | C17—C18—C19—C24 | −0.3 (4) |
N1—C1—C2—C3 | −179.9 (2) | C17—C18—C19—C20 | 179.6 (2) |
C6—C1—C2—C3 | −0.3 (4) | C18—C19—C20—C21 | −179.2 (2) |
C1—C2—C3—C4 | 0.0 (4) | C24—C19—C20—C21 | 0.7 (4) |
C2—C3—C4—C5 | −0.1 (4) | C19—C20—C21—C22 | −1.1 (4) |
C2—C3—C4—C7 | 179.7 (2) | C19—C20—C21—C25 | −179.6 (2) |
C3—C4—C5—C6 | 0.5 (4) | C20—C21—C22—C23 | 1.3 (4) |
C7—C4—C5—C6 | −179.3 (2) | C25—C21—C22—C23 | 179.9 (2) |
C4—C5—C6—C8 | 179.6 (2) | C21—C22—C23—C24 | −1.2 (4) |
C4—C5—C6—C1 | −0.7 (4) | C16—N3—C24—C23 | −179.1 (2) |
N1—C1—C6—C8 | 0.0 (4) | Fe1—N3—C24—C23 | 4.4 (3) |
C2—C1—C6—C8 | −179.7 (2) | C16—N3—C24—C19 | 0.4 (3) |
N1—C1—C6—C5 | −179.7 (2) | Fe1—N3—C24—C19 | −176.16 (17) |
C2—C1—C6—C5 | 0.6 (3) | C22—C23—C24—N3 | −179.8 (2) |
C5—C6—C8—C9 | 179.7 (2) | C22—C23—C24—C19 | 0.8 (4) |
C1—C6—C8—C9 | 0.1 (4) | C18—C19—C24—N3 | −0.1 (4) |
C6—C8—C9—C10 | −0.4 (4) | C20—C19—C24—N3 | −180.0 (2) |
C1—N1—C10—C9 | −0.7 (3) | C18—C19—C24—C23 | 179.4 (2) |
Fe1—N1—C10—C9 | −176.04 (19) | C20—C19—C24—C23 | −0.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···Cl2i | 0.95 | 2.70 | 3.561 (2) | 151 |
C17—H17···Cl1ii | 0.95 | 2.73 | 3.538 (4) | 144 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [FeCl2(C25H19N3)] |
Mr | 488.18 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 9.6228 (7), 10.2558 (8), 10.7324 (8) |
α, β, γ (°) | 94.352 (1), 95.481 (1), 96.121 (1) |
V (Å3) | 1044.35 (14) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.00 |
Crystal size (mm) | 0.30 × 0.10 × 0.05 |
Data collection | |
Diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.754, 0.952 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9910, 4757, 3954 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.108, 1.05 |
No. of reflections | 4757 |
No. of parameters | 292 |
No. of restraints | 7 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.54, −0.44 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).
Fe1—N1 | 2.2386 (19) | Fe1—Cl1 | 2.3636 (8) |
Fe1—N2 | 2.103 (2) | Fe1—Cl2 | 2.2748 (7) |
Fe1—N3 | 2.2523 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···Cl2i | 0.95 | 2.70 | 3.561 (2) | 151 |
C17—H17···Cl1ii | 0.95 | 2.73 | 3.538 (4) | 144 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+2, −z+1. |
Acknowledgements
We thank the Graduate Experimental Research Fund of Northwest University (project No. 09YSY22), the National Natural Science Foundation of China (No.20971104) and the University of Malaya for supporting this study.
References
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Buu-Hoi, N. P., Perin, F. & Jacquignon, P. (1965). J. Heterocycl. Chem. 2, 7–10. CrossRef CAS Google Scholar
Li, X.-P., Liu, Y.-Y. & Zhao, J.-S. (2010). Acta Cryst. E66, m1215. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
A recent study reported the chromium(III) chloride adduct of 2,6-bis(p-bromphenylimino)pyridine; the N-heterocycle chelates to the metal atom in a terdentate manner (Li et al., 2010). Bis[2'-(6-methylquinolinyl)]pyridine has a similar set of donor sites capable of binding in this manner, as demonstrated in the present iron dichloride adduct (Scheme I, Fig. 1 and Table 1). In the molecule of FeCl2(C25H19N3), the three N atoms span the axial–equatorial-axial sites of the trigonal bipyramidal coordination polyhedron; the geometry of Fe is 32% distorted from the trigonal bipyramid along the Berry pseudorotation pathway. Intermolecular C—H···Cl hydrogen bonding occurs in the crystal structure (Table 2).