Literature DB >> 21587437

[2,6-Bis(6-methyl-quinolin-2-yl)pyridine-κN,N',N'']dichloridomanganese(II).

Xiao-Ping Li, Jian-She Zhao, Seik Weng Ng.   

Abstract

In the mol-ecule of the title compound, [MnCl(2)(C(25)H(19)N(3))], the three N atoms span the axial-equatorial-axial sites of the trigonal-bipyramidal coordination polyhedron; the geometry of the Mn(II) atom is 34% distorted from trigonal-bipyramidal (towards square-pyramidal along the Berry pseudorotation pathway). One of the Cl atoms is disordered over two positions in a 0.82 (3):0.18 (3) ratio. Weak inter-molecular C-H⋯Cl hydrogen bonding occurs in the crystal structure.

Entities:  

Year:  2010        PMID: 21587437      PMCID: PMC2983179          DOI: 10.1107/S1600536810037037

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


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

[MnCl2(C25H19N3)] M = 487.27 Triclinic, a = 9.6763 (8) Å b = 10.3721 (9) Å c = 10.5757 (9) Å α = 95.099 (1)° β = 97.499 (1)° γ = 95.411 (1)° V = 1042.13 (15) Å3 Z = 2 Mo Kα radiation μ = 0.91 mm−1 T = 100 K 0.30 × 0.10 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.772, T max = 0.956 10000 measured reflections 4760 independent reflections 3704 reflections with I > 2σ(I) R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.050 wR(F 2) = 0.151 S = 1.03 4760 reflections 292 parameters 7 restraints H-atom parameters constrained Δρmax = 0.61 e Å−3 Δρmin = −0.62 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: 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 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810037037/xu5031sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037037/xu5031Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[MnCl2(C25H19N3)]Z = 2
Mr = 487.27F(000) = 498
Triclinic, P1Dx = 1.553 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6763 (8) ÅCell parameters from 2981 reflections
b = 10.3721 (9) Åθ = 2.7–28.1°
c = 10.5757 (9) ŵ = 0.91 mm1
α = 95.099 (1)°T = 100 K
β = 97.499 (1)°Prism, orange
γ = 95.411 (1)°0.30 × 0.10 × 0.05 mm
V = 1042.13 (15) Å3
Bruker SMART APEX diffractometer4760 independent reflections
Radiation source: fine-focus sealed tube3704 reflections with I > 2σ(I)
graphiteRint = 0.031
ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.772, Tmax = 0.956k = −13→13
10000 measured reflectionsl = −13→13
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0695P)2 + 1.8956P] where P = (Fo2 + 2Fc2)/3
4760 reflections(Δ/σ)max = 0.001
292 parametersΔρmax = 0.61 e Å3
7 restraintsΔρmin = −0.62 e Å3
xyzUiso*/UeqOcc. (<1)
Mn10.34023 (5)0.80899 (5)0.22288 (5)0.02281 (16)
Cl10.1607 (7)0.7350 (2)0.3414 (7)0.0280 (8)0.82 (3)
Cl1'0.202 (4)0.7316 (11)0.378 (3)0.033 (4)0.18 (3)
Cl20.26785 (12)0.84219 (10)0.00968 (9)0.0408 (3)
N10.4349 (3)0.6152 (3)0.1893 (3)0.0246 (6)
N20.5637 (3)0.8443 (3)0.2966 (3)0.0218 (6)
N30.3883 (3)1.0248 (3)0.3127 (3)0.0233 (6)
C10.3623 (4)0.5007 (3)0.1294 (3)0.0238 (7)
C20.2180 (4)0.4980 (4)0.0882 (4)0.0315 (8)
H20.17240.57440.10120.038*
C30.1431 (4)0.3852 (3)0.0292 (4)0.0307 (8)
H30.04550.38480.00200.037*
C40.2061 (4)0.2698 (3)0.0075 (3)0.0258 (7)
C50.3468 (4)0.2715 (3)0.0468 (3)0.0268 (7)
H50.39100.19450.03260.032*
C60.4273 (4)0.3862 (3)0.1081 (3)0.0268 (7)
C70.1162 (4)0.1491 (3)−0.0556 (4)0.0300 (8)
H7A0.17530.0788−0.06920.045*
H7B0.06760.1671−0.13840.045*
H7C0.04700.1226−0.00040.045*
C80.5703 (5)0.3949 (4)0.1535 (4)0.0449 (10)
H80.61960.32050.14310.054*
C90.6412 (5)0.5111 (5)0.2137 (4)0.0452 (10)
H90.73820.51560.24540.054*
C100.5714 (3)0.6197 (3)0.2276 (3)0.0218 (7)
C110.6441 (3)0.7459 (3)0.2886 (3)0.0234 (7)
C120.7870 (3)0.7643 (4)0.3346 (3)0.0250 (7)
H120.84300.69410.32870.030*
C130.8453 (4)0.8864 (4)0.3890 (3)0.0294 (8)
H130.94260.90130.42010.035*
C140.7620 (4)0.9875 (3)0.3982 (3)0.0268 (7)
H140.80071.07190.43580.032*
C150.6196 (3)0.9620 (3)0.3508 (3)0.0224 (7)
C160.5199 (4)1.0619 (3)0.3558 (3)0.0257 (7)
C170.5635 (5)1.1919 (5)0.4056 (5)0.0507 (11)
H170.65971.21820.43560.061*
C180.4660 (5)1.2819 (5)0.4109 (5)0.0514 (12)
H180.49631.36960.44420.062*
C190.3264 (4)1.2453 (3)0.3686 (3)0.0262 (7)
C200.2218 (4)1.3312 (3)0.3691 (3)0.0281 (8)
H200.24701.41960.40250.034*
C210.0836 (4)1.2892 (3)0.3220 (3)0.0288 (8)
C220.0497 (4)1.1579 (3)0.2710 (3)0.0273 (7)
H22−0.04481.12800.23700.033*
C230.1494 (4)1.0724 (3)0.2691 (3)0.0266 (7)
H230.12300.98440.23490.032*
C240.2906 (4)1.1140 (3)0.3175 (3)0.0252 (7)
C25−0.0286 (4)1.3793 (4)0.3212 (4)0.0363 (9)
H25A0.01441.46970.33040.055*
H25B−0.08161.36540.39260.055*
H25C−0.09201.36180.24000.055*
U11U22U33U12U13U23
Mn10.0177 (3)0.0206 (3)0.0285 (3)0.00071 (19)0.0000 (2)−0.00009 (19)
Cl10.0207 (13)0.0246 (6)0.0377 (16)−0.0016 (7)0.0049 (13)0.0008 (7)
Cl1'0.026 (7)0.031 (3)0.040 (6)−0.003 (3)0.008 (6)−0.003 (3)
Cl20.0500 (6)0.0386 (5)0.0323 (5)0.0163 (4)−0.0063 (4)0.0018 (4)
N10.0245 (15)0.0239 (14)0.0248 (14)0.0002 (11)0.0016 (12)0.0044 (11)
N20.0199 (14)0.0219 (14)0.0222 (13)−0.0013 (11)0.0007 (11)0.0013 (10)
N30.0243 (15)0.0230 (14)0.0230 (14)0.0021 (11)0.0056 (11)0.0013 (11)
C10.0210 (17)0.0246 (16)0.0240 (16)−0.0048 (13)−0.0002 (13)0.0051 (13)
C20.0276 (19)0.0251 (18)0.040 (2)0.0040 (14)0.0006 (16)0.0013 (15)
C30.0240 (18)0.0284 (18)0.036 (2)−0.0020 (14)−0.0037 (15)0.0017 (15)
C40.0324 (19)0.0213 (16)0.0234 (16)−0.0006 (14)0.0044 (14)0.0035 (13)
C50.0303 (19)0.0253 (17)0.0259 (17)0.0047 (14)0.0050 (14)0.0062 (13)
C60.0251 (18)0.0309 (18)0.0246 (17)0.0016 (14)0.0022 (14)0.0077 (14)
C70.033 (2)0.0240 (17)0.0318 (19)−0.0015 (15)0.0034 (15)0.0036 (14)
C80.045 (3)0.039 (2)0.052 (3)0.0141 (19)0.009 (2)0.0015 (19)
C90.032 (2)0.054 (3)0.048 (2)0.0101 (19)0.0015 (19)0.000 (2)
C100.0163 (15)0.0232 (16)0.0257 (16)−0.0003 (12)0.0036 (13)0.0032 (13)
C110.0203 (16)0.0299 (18)0.0200 (15)0.0047 (13)0.0012 (13)0.0035 (13)
C120.0174 (16)0.0330 (18)0.0236 (16)0.0010 (13)0.0008 (13)0.0017 (14)
C130.0174 (17)0.045 (2)0.0247 (17)−0.0012 (15)0.0012 (13)0.0034 (15)
C140.0236 (18)0.0297 (18)0.0241 (16)−0.0066 (14)0.0020 (13)−0.0022 (14)
C150.0206 (16)0.0256 (17)0.0198 (15)−0.0034 (13)0.0030 (12)0.0019 (12)
C160.0261 (18)0.0268 (17)0.0225 (16)−0.0050 (14)0.0030 (13)0.0017 (13)
C170.047 (3)0.055 (3)0.047 (3)0.000 (2)0.002 (2)0.003 (2)
C180.060 (3)0.041 (2)0.051 (3)−0.001 (2)0.007 (2)0.002 (2)
C190.0278 (18)0.0258 (17)0.0253 (17)0.0009 (14)0.0050 (14)0.0042 (13)
C200.034 (2)0.0226 (17)0.0284 (18)0.0020 (14)0.0062 (15)0.0050 (13)
C210.033 (2)0.0279 (18)0.0280 (17)0.0068 (15)0.0084 (15)0.0079 (14)
C220.0265 (18)0.0276 (18)0.0280 (17)0.0024 (14)0.0039 (14)0.0045 (14)
C230.0272 (18)0.0220 (16)0.0294 (17)0.0005 (14)0.0030 (14)−0.0002 (13)
C240.0285 (18)0.0251 (17)0.0231 (16)0.0018 (14)0.0064 (14)0.0053 (13)
C250.034 (2)0.0282 (19)0.048 (2)0.0066 (16)0.0070 (18)0.0060 (17)
Mn1—N12.305 (3)C9—H90.9500
Mn1—N22.186 (3)C10—C111.477 (5)
Mn1—N32.332 (3)C11—C121.393 (5)
Mn1—Cl12.3802 (17)C12—C131.381 (5)
Mn1—Cl1'2.388 (7)C12—H120.9500
Mn1—Cl22.3375 (11)C13—C141.385 (5)
N1—C101.325 (4)C13—H130.9500
N1—C11.378 (4)C14—C151.395 (5)
N2—C151.335 (4)C14—H140.9500
N2—C111.344 (4)C15—C161.483 (5)
N3—C161.305 (4)C16—C171.408 (6)
N3—C241.387 (5)C17—C181.391 (7)
C1—C21.405 (5)C17—H170.9500
C1—C61.410 (5)C18—C191.373 (6)
C2—C31.370 (5)C18—H180.9500
C2—H20.9500C19—C201.410 (5)
C3—C41.408 (5)C19—C241.413 (5)
C3—H30.9500C20—C211.380 (5)
C4—C51.369 (5)C20—H200.9500
C4—C71.505 (5)C21—C221.411 (5)
C5—C61.414 (5)C21—C251.498 (5)
C5—H50.9500C22—C231.372 (5)
C6—C81.396 (6)C22—H220.9500
C7—H7A0.9800C23—C241.407 (5)
C7—H7B0.9800C23—H230.9500
C7—H7C0.9800C25—H25A0.9800
C8—C91.386 (6)C25—H25B0.9800
C8—H80.9500C25—H25C0.9800
C9—C101.373 (6)
N2—Mn1—N172.62 (10)C8—C9—H9119.9
N2—Mn1—N371.80 (10)N1—C10—C9121.3 (3)
N1—Mn1—N3144.34 (10)N1—C10—C11117.0 (3)
N2—Mn1—Cl2118.47 (8)C9—C10—C11121.6 (3)
N1—Mn1—Cl299.09 (8)N2—C11—C12121.2 (3)
N3—Mn1—Cl299.72 (8)N2—C11—C10115.7 (3)
N2—Mn1—Cl1125.3 (2)C12—C11—C10123.1 (3)
N1—Mn1—Cl198.25 (11)C13—C12—C11118.6 (3)
N3—Mn1—Cl1100.18 (10)C13—C12—H12120.7
Cl2—Mn1—Cl1116.2 (2)C11—C12—H12120.7
N2—Mn1—Cl1'112.7 (11)C12—C13—C14120.1 (3)
N1—Mn1—Cl1'93.8 (5)C12—C13—H13120.0
N3—Mn1—Cl1'97.6 (3)C14—C13—H13120.0
Cl2—Mn1—Cl1'128.8 (11)C13—C14—C15118.2 (3)
Cl1—Mn1—Cl1'12.6 (9)C13—C14—H14120.9
C10—N1—C1119.5 (3)C15—C14—H14120.9
C10—N1—Mn1115.3 (2)N2—C15—C14121.6 (3)
C1—N1—Mn1125.2 (2)N2—C15—C16115.2 (3)
C15—N2—C11120.2 (3)C14—C15—C16123.2 (3)
C15—N2—Mn1120.4 (2)N3—C16—C17120.5 (4)
C11—N2—Mn1119.4 (2)N3—C16—C15117.4 (3)
C16—N3—C24119.6 (3)C17—C16—C15122.1 (3)
C16—N3—Mn1115.1 (2)C18—C17—C16120.2 (4)
C24—N3—Mn1125.2 (2)C18—C17—H17119.9
N1—C1—C2118.7 (3)C16—C17—H17119.9
N1—C1—C6122.5 (3)C19—C18—C17120.6 (4)
C2—C1—C6118.8 (3)C19—C18—H18119.7
C3—C2—C1119.9 (3)C17—C18—H18119.7
C3—C2—H2120.1C18—C19—C20123.9 (4)
C1—C2—H2120.1C18—C19—C24116.1 (4)
C2—C3—C4122.1 (3)C20—C19—C24120.0 (3)
C2—C3—H3118.9C21—C20—C19121.2 (3)
C4—C3—H3118.9C21—C20—H20119.4
C5—C4—C3118.5 (3)C19—C20—H20119.4
C5—C4—C7122.5 (3)C20—C21—C22118.1 (3)
C3—C4—C7118.9 (3)C20—C21—C25121.9 (3)
C4—C5—C6120.9 (3)C22—C21—C25120.0 (3)
C4—C5—H5119.6C23—C22—C21121.8 (3)
C6—C5—H5119.6C23—C22—H22119.1
C8—C6—C1115.9 (3)C21—C22—H22119.1
C8—C6—C5124.3 (4)C22—C23—C24120.5 (3)
C1—C6—C5119.8 (3)C22—C23—H23119.8
C4—C7—H7A109.5C24—C23—H23119.8
C4—C7—H7B109.5N3—C24—C23118.7 (3)
H7A—C7—H7B109.5N3—C24—C19122.9 (3)
C4—C7—H7C109.5C23—C24—C19118.4 (3)
H7A—C7—H7C109.5C21—C25—H25A109.5
H7B—C7—H7C109.5C21—C25—H25B109.5
C9—C8—C6120.6 (4)H25A—C25—H25B109.5
C9—C8—H8119.7C21—C25—H25C109.5
C6—C8—H8119.7H25A—C25—H25C109.5
C10—C9—C8120.1 (4)H25B—C25—H25C109.5
C10—C9—H9119.9
N2—Mn1—N1—C10−0.7 (2)C1—N1—C10—C11178.6 (3)
N3—Mn1—N1—C10−4.7 (3)Mn1—N1—C10—C111.2 (4)
Cl2—Mn1—N1—C10116.4 (2)C8—C9—C10—N12.9 (6)
Cl1—Mn1—N1—C10−125.2 (3)C8—C9—C10—C11−178.6 (4)
Cl1'—Mn1—N1—C10−113.3 (10)C15—N2—C11—C12−0.8 (5)
N2—Mn1—N1—C1−177.9 (3)Mn1—N2—C11—C12−179.9 (2)
N3—Mn1—N1—C1178.1 (2)C15—N2—C11—C10179.6 (3)
Cl2—Mn1—N1—C1−60.8 (3)Mn1—N2—C11—C100.5 (4)
Cl1—Mn1—N1—C157.5 (3)N1—C10—C11—N2−1.2 (4)
Cl1'—Mn1—N1—C169.4 (10)C9—C10—C11—N2−179.8 (3)
N1—Mn1—N2—C15−179.0 (3)N1—C10—C11—C12179.2 (3)
N3—Mn1—N2—C15−1.5 (2)C9—C10—C11—C120.6 (5)
Cl2—Mn1—N2—C1589.9 (2)N2—C11—C12—C13−0.1 (5)
Cl1—Mn1—N2—C15−91.2 (3)C10—C11—C12—C13179.4 (3)
Cl1'—Mn1—N2—C15−92.3 (4)C11—C12—C13—C140.7 (5)
N1—Mn1—N2—C110.1 (2)C12—C13—C14—C15−0.3 (5)
N3—Mn1—N2—C11177.6 (3)C11—N2—C15—C141.1 (5)
Cl2—Mn1—N2—C11−91.0 (2)Mn1—N2—C15—C14−179.7 (2)
Cl1—Mn1—N2—C1187.9 (3)C11—N2—C15—C16−179.1 (3)
Cl1'—Mn1—N2—C1186.8 (4)Mn1—N2—C15—C160.0 (4)
N2—Mn1—N3—C163.0 (2)C13—C14—C15—N2−0.6 (5)
N1—Mn1—N3—C166.9 (3)C13—C14—C15—C16179.7 (3)
Cl2—Mn1—N3—C16−114.0 (2)C24—N3—C16—C17−0.8 (5)
Cl1—Mn1—N3—C16127.0 (3)Mn1—N3—C16—C17176.4 (3)
Cl1'—Mn1—N3—C16114.4 (11)C24—N3—C16—C15178.8 (3)
N2—Mn1—N3—C24180.0 (3)Mn1—N3—C16—C15−4.0 (4)
N1—Mn1—N3—C24−176.0 (2)N2—C15—C16—N32.8 (4)
Cl2—Mn1—N3—C2463.1 (3)C14—C15—C16—N3−177.4 (3)
Cl1—Mn1—N3—C24−56.0 (3)N2—C15—C16—C17−177.6 (3)
Cl1'—Mn1—N3—C24−68.5 (11)C14—C15—C16—C172.2 (5)
C10—N1—C1—C2−179.3 (3)N3—C16—C17—C180.9 (6)
Mn1—N1—C1—C2−2.2 (4)C15—C16—C17—C18−178.7 (4)
C10—N1—C1—C60.8 (5)C16—C17—C18—C190.4 (7)
Mn1—N1—C1—C6177.9 (2)C17—C18—C19—C20−179.0 (4)
N1—C1—C2—C3−179.5 (3)C17—C18—C19—C24−1.6 (6)
C6—C1—C2—C30.3 (5)C18—C19—C20—C21178.2 (4)
C1—C2—C3—C4−0.1 (6)C24—C19—C20—C210.9 (5)
C2—C3—C4—C5−0.2 (6)C19—C20—C21—C22−1.1 (5)
C2—C3—C4—C7178.8 (3)C19—C20—C21—C25−179.6 (3)
C3—C4—C5—C60.2 (5)C20—C21—C22—C231.0 (5)
C7—C4—C5—C6−178.7 (3)C25—C21—C22—C23179.6 (3)
N1—C1—C6—C81.0 (5)C21—C22—C23—C24−0.7 (5)
C2—C1—C6—C8−178.8 (4)C16—N3—C24—C23179.3 (3)
N1—C1—C6—C5179.6 (3)Mn1—N3—C24—C232.4 (4)
C2—C1—C6—C5−0.3 (5)C16—N3—C24—C19−0.5 (5)
C4—C5—C6—C8178.4 (4)Mn1—N3—C24—C19−177.4 (2)
C4—C5—C6—C10.0 (5)C22—C23—C24—N3−179.3 (3)
C1—C6—C8—C9−0.9 (6)C22—C23—C24—C190.4 (5)
C5—C6—C8—C9−179.4 (4)C18—C19—C24—N31.7 (5)
C6—C8—C9—C10−0.9 (7)C20—C19—C24—N3179.2 (3)
C1—N1—C10—C9−2.8 (5)C18—C19—C24—C23−178.1 (4)
Mn1—N1—C10—C9179.8 (3)C20—C19—C24—C23−0.5 (5)
D—H···AD—HH···AD···AD—H···A
C8—H8···Cl2i0.952.643.486 (5)149
C17—H17···Cl1ii0.952.723.500 (9)140
Table 1

Selected bond lengths (Å)

Mn1—N12.305 (3)
Mn1—N22.186 (3)
Mn1—N32.332 (3)
Mn1—Cl12.3802 (17)
Mn1—Cl22.3375 (11)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
C8—H8⋯Cl2i0.952.643.486 (5)149
C17—H17⋯Cl1ii0.952.723.500 (9)140

Symmetry codes: (i) ; (ii) .

  2 in total

1.  A short history of SHELX.

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

2.  {2,6-Bis[(4-bromo-phen-yl)imino-meth-yl]pyridine-κN,N',N''}trichlorido-chromium(III).

Authors:  Xiao-Ping Li; Yong-Yong Liu; Jian-She Zhao
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-09-08
  2 in total

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