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The synthesis and crystal structure of the multidentate PPN ligand 2-[bis­(diiso­propyl­phosphanyl)methyl]-6-methyl­pyridine (L), C19H35NP2, are described. In the isostructural tetra­hedral Fe and Co complexes of type LMCl2 (M = Fe, Co), namely {2-[bis­(diiso­propyl­phosphanyl)methyl]-6-methyl­pyri­dine-κ2P,N}di­chlorido­iron(II), [FeCl2(C19H35NP2)], and {2-[bis(diiso­propyl­phos­phanyl)methyl]-6-methyl­pyridine-κ2P,N}di­chloridocobalt(II), [CoCl2(C19H35NP2)], the ligand adopts a bidentate P,N-coordination, whereas in the case of the octa­hedral Mn complex {2-[bis­(diiso­propyl­phosphanyl)methyl]-6-methyl­pyri­dine-κ2P,P′}bromidotricarbonylmanganese(I), [MnBr(C19H35NP2)(CO)3], the ligand coordinates via both P atoms to the metal centre.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961701261X/ov3095sup1.cif
Contains datablocks 1, 2, 3, 4, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961701261X/ov30951sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961701261X/ov30952sup3.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961701261X/ov30953sup4.hkl
Contains datablock 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961701261X/ov30954sup5.hkl
Contains datablock 4

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961701261X/ov30951sup6.cml
Supplementary material

CCDC references: 1550599; 1550598; 1550597; 1550596

Computing details top

For all structures, data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2015); software used to prepare material for publication: publCIF (Westrip, 2010).

2-[Bis(diisopropylphosphanyl)methyl]-6-methylpyridine (1) top
Crystal data top
C19H35NP2F(000) = 744
Mr = 339.42Dx = 1.095 Mg m3
Monoclinic, P2/cMo Kα radiation, λ = 0.71073 Å
a = 16.2905 (5) ÅCell parameters from 9990 reflections
b = 6.7510 (2) Åθ = 2.4–30.4°
c = 18.9112 (6) ŵ = 0.21 mm1
β = 98.2024 (11)°T = 150 K
V = 2058.52 (11) Å3Prism, colourless
Z = 40.38 × 0.16 × 0.07 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
4970 independent reflections
Radiation source: fine-focus sealed tube4231 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm-1Rint = 0.032
φ and ω scansθmax = 28.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
h = 2121
Tmin = 0.93, Tmax = 0.98k = 88
37883 measured reflectionsl = 2424
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0487P)2 + 0.9053P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
4970 reflectionsΔρmax = 0.69 e Å3
208 parametersΔρmin = 0.21 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.77919 (8)0.8830 (2)0.42774 (6)0.0213 (3)
C20.78860 (8)1.0883 (2)0.42979 (7)0.0259 (3)
H20.75351.17050.39780.031*
C30.84985 (9)1.1701 (2)0.47916 (8)0.0317 (3)
H30.85721.30960.48200.038*
C40.90014 (9)1.0459 (2)0.52422 (8)0.0322 (3)
H40.94321.09890.55810.039*
C50.88726 (8)0.8429 (2)0.51961 (7)0.0272 (3)
C60.71201 (8)0.79161 (19)0.37513 (6)0.0205 (2)
H60.66600.89040.36570.025*
C70.93883 (10)0.7011 (3)0.56840 (8)0.0392 (4)
H7A0.90240.61690.59250.059*
H7B0.97610.77570.60410.059*
H7C0.97170.61820.54040.059*
C80.63311 (8)0.6310 (2)0.49637 (7)0.0263 (3)
H80.57580.57610.49440.032*
C90.62598 (10)0.8512 (2)0.51338 (8)0.0337 (3)
H9A0.59630.86690.55460.051*
H9B0.59550.91930.47200.051*
H9C0.68160.90850.52450.051*
C100.68569 (10)0.5220 (3)0.55748 (8)0.0396 (4)
H10A0.74240.57410.56350.059*
H10B0.68660.38030.54650.059*
H10C0.66190.54170.60170.059*
C110.56638 (8)0.5504 (2)0.34873 (7)0.0260 (3)
H110.57980.54730.29880.031*
C120.52500 (10)0.3524 (3)0.36082 (9)0.0381 (4)
H12A0.50890.35030.40880.057*
H12B0.56400.24420.35630.057*
H12C0.47560.33580.32510.057*
C130.50540 (9)0.7204 (3)0.35190 (9)0.0376 (4)
H13A0.45580.69730.31700.056*
H13B0.53150.84510.34070.056*
H13C0.48970.72800.40000.056*
C140.85088 (8)0.6208 (2)0.31272 (7)0.0256 (3)
H140.84880.54250.35730.031*
C150.92280 (9)0.7664 (2)0.32984 (8)0.0314 (3)
H15A0.97370.69330.34720.047*
H15B0.91040.85930.36670.047*
H15C0.93040.83990.28660.047*
C160.87039 (10)0.4719 (2)0.25599 (9)0.0381 (4)
H16A0.87710.54270.21190.057*
H16B0.82470.37670.24620.057*
H16C0.92180.40110.27360.057*
C170.76112 (9)0.9705 (2)0.24781 (7)0.0257 (3)
H170.80241.04570.28180.031*
C180.67987 (10)1.0874 (3)0.23489 (9)0.0372 (4)
H18A0.68891.21200.21060.056*
H18B0.66101.11590.28080.056*
H18C0.63771.00900.20500.056*
C190.79489 (11)0.9447 (3)0.17675 (8)0.0371 (4)
H19A0.75580.86580.14400.056*
H19B0.84860.87670.18520.056*
H19C0.80191.07500.15560.056*
N10.82729 (7)0.76162 (17)0.47200 (6)0.0230 (2)
P10.66772 (2)0.56127 (5)0.40902 (2)0.02128 (9)
P20.74421 (2)0.72323 (5)0.28634 (2)0.02138 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0207 (6)0.0257 (7)0.0190 (5)0.0024 (5)0.0079 (5)0.0024 (5)
C20.0270 (6)0.0248 (7)0.0270 (6)0.0011 (5)0.0075 (5)0.0031 (5)
C30.0339 (7)0.0291 (7)0.0340 (7)0.0081 (6)0.0108 (6)0.0097 (6)
C40.0275 (7)0.0435 (9)0.0259 (7)0.0111 (6)0.0048 (5)0.0104 (6)
C50.0222 (6)0.0402 (8)0.0200 (6)0.0025 (6)0.0058 (5)0.0011 (6)
C60.0196 (6)0.0219 (6)0.0203 (6)0.0008 (5)0.0039 (4)0.0004 (5)
C70.0305 (8)0.0552 (11)0.0300 (7)0.0010 (7)0.0025 (6)0.0066 (7)
C80.0263 (6)0.0316 (7)0.0224 (6)0.0041 (6)0.0081 (5)0.0002 (5)
C90.0359 (8)0.0377 (8)0.0300 (7)0.0036 (7)0.0131 (6)0.0061 (6)
C100.0408 (9)0.0524 (10)0.0265 (7)0.0007 (8)0.0082 (6)0.0084 (7)
C110.0234 (6)0.0307 (7)0.0242 (6)0.0068 (5)0.0044 (5)0.0035 (5)
C120.0350 (8)0.0373 (9)0.0443 (9)0.0146 (7)0.0140 (7)0.0091 (7)
C130.0248 (7)0.0416 (9)0.0437 (9)0.0005 (6)0.0043 (6)0.0007 (7)
C140.0242 (6)0.0282 (7)0.0255 (6)0.0003 (5)0.0069 (5)0.0004 (5)
C150.0226 (6)0.0414 (9)0.0306 (7)0.0023 (6)0.0050 (5)0.0055 (6)
C160.0385 (8)0.0335 (8)0.0449 (9)0.0005 (7)0.0148 (7)0.0100 (7)
C170.0289 (7)0.0277 (7)0.0205 (6)0.0052 (5)0.0032 (5)0.0030 (5)
C180.0357 (8)0.0386 (9)0.0365 (8)0.0018 (7)0.0027 (6)0.0130 (7)
C190.0481 (9)0.0409 (9)0.0239 (7)0.0063 (7)0.0106 (6)0.0054 (6)
N10.0217 (5)0.0288 (6)0.0194 (5)0.0025 (4)0.0055 (4)0.0002 (4)
P10.02202 (17)0.02089 (17)0.02170 (16)0.00085 (12)0.00575 (12)0.00117 (12)
P20.02138 (17)0.02478 (18)0.01823 (16)0.00447 (13)0.00370 (12)0.00078 (12)
Geometric parameters (Å, º) top
C1—N11.3413 (17)C11—P11.8691 (14)
C1—C21.3943 (19)C11—H111.0000
C1—C61.5025 (17)C12—H12A0.9800
C2—C31.3807 (19)C12—H12B0.9800
C2—H20.9500C12—H12C0.9800
C3—C41.379 (2)C13—H13A0.9800
C3—H30.9500C13—H13B0.9800
C4—C51.387 (2)C13—H13C0.9800
C4—H40.9500C14—C151.528 (2)
C5—N11.3473 (17)C14—C161.536 (2)
C5—C71.501 (2)C14—P21.8708 (14)
C6—P11.8659 (13)C14—H141.0000
C6—P21.8866 (13)C15—H15A0.9800
C6—H61.0000C15—H15B0.9800
C7—H7A0.9800C15—H15C0.9800
C7—H7B0.9800C16—H16A0.9800
C7—H7C0.9800C16—H16B0.9800
C8—C101.526 (2)C16—H16C0.9800
C8—C91.529 (2)C17—C181.530 (2)
C8—P11.8799 (13)C17—C191.5330 (19)
C8—H81.0000C17—P21.8575 (14)
C9—H9A0.9800C17—H171.0000
C9—H9B0.9800C18—H18A0.9800
C9—H9C0.9800C18—H18B0.9800
C10—H10A0.9800C18—H18C0.9800
C10—H10B0.9800C19—H19A0.9800
C10—H10C0.9800C19—H19B0.9800
C11—C131.525 (2)C19—H19C0.9800
C11—C121.529 (2)
N1—C1—C2122.54 (12)H12A—C12—H12B109.5
N1—C1—C6117.89 (12)C11—C12—H12C109.5
C2—C1—C6119.56 (12)H12A—C12—H12C109.5
C3—C2—C1118.83 (13)H12B—C12—H12C109.5
C3—C2—H2120.6C11—C13—H13A109.5
C1—C2—H2120.6C11—C13—H13B109.5
C4—C3—C2118.90 (14)H13A—C13—H13B109.5
C4—C3—H3120.6C11—C13—H13C109.5
C2—C3—H3120.6H13A—C13—H13C109.5
C3—C4—C5119.37 (13)H13B—C13—H13C109.5
C3—C4—H4120.3C15—C14—C16109.89 (11)
C5—C4—H4120.3C15—C14—P2118.26 (10)
N1—C5—C4122.23 (13)C16—C14—P2109.43 (10)
N1—C5—C7116.09 (14)C15—C14—H14106.2
C4—C5—C7121.68 (13)C16—C14—H14106.2
C1—C6—P1113.30 (9)P2—C14—H14106.2
C1—C6—P2114.91 (8)C14—C15—H15A109.5
P1—C6—P2105.79 (6)C14—C15—H15B109.5
C1—C6—H6107.5H15A—C15—H15B109.5
P1—C6—H6107.5C14—C15—H15C109.5
P2—C6—H6107.5H15A—C15—H15C109.5
C5—C7—H7A109.5H15B—C15—H15C109.5
C5—C7—H7B109.5C14—C16—H16A109.5
H7A—C7—H7B109.5C14—C16—H16B109.5
C5—C7—H7C109.5H16A—C16—H16B109.5
H7A—C7—H7C109.5C14—C16—H16C109.5
H7B—C7—H7C109.5H16A—C16—H16C109.5
C10—C8—C9111.15 (13)H16B—C16—H16C109.5
C10—C8—P1109.78 (10)C18—C17—C19109.21 (12)
C9—C8—P1118.01 (10)C18—C17—P2110.66 (10)
C10—C8—H8105.7C19—C17—P2109.49 (10)
C9—C8—H8105.7C18—C17—H17109.2
P1—C8—H8105.7C19—C17—H17109.2
C8—C9—H9A109.5P2—C17—H17109.2
C8—C9—H9B109.5C17—C18—H18A109.5
H9A—C9—H9B109.5C17—C18—H18B109.5
C8—C9—H9C109.5H18A—C18—H18B109.5
H9A—C9—H9C109.5C17—C18—H18C109.5
H9B—C9—H9C109.5H18A—C18—H18C109.5
C8—C10—H10A109.5H18B—C18—H18C109.5
C8—C10—H10B109.5C17—C19—H19A109.5
H10A—C10—H10B109.5C17—C19—H19B109.5
C8—C10—H10C109.5H19A—C19—H19B109.5
H10A—C10—H10C109.5C17—C19—H19C109.5
H10B—C10—H10C109.5H19A—C19—H19C109.5
C13—C11—C12110.40 (12)H19B—C19—H19C109.5
C13—C11—P1118.04 (10)C1—N1—C5118.13 (12)
C12—C11—P1108.25 (10)C6—P1—C11100.05 (6)
C13—C11—H11106.5C6—P1—C8105.80 (6)
C12—C11—H11106.5C11—P1—C8101.32 (6)
P1—C11—H11106.5C17—P2—C14104.64 (6)
C11—C12—H12A109.5C17—P2—C6101.82 (6)
C11—C12—H12B109.5C14—P2—C6102.64 (6)
N1—C1—C2—C30.1 (2)C12—C11—P1—C6171.88 (10)
C6—C1—C2—C3179.06 (11)C13—C11—P1—C846.65 (12)
C1—C2—C3—C40.7 (2)C12—C11—P1—C879.61 (11)
C2—C3—C4—C50.9 (2)C10—C8—P1—C6113.91 (11)
C3—C4—C5—N10.5 (2)C9—C8—P1—C614.81 (12)
C3—C4—C5—C7178.59 (13)C10—C8—P1—C11142.11 (11)
N1—C1—C6—P131.99 (14)C9—C8—P1—C1189.17 (12)
C2—C1—C6—P1147.01 (10)C18—C17—P2—C14170.68 (10)
N1—C1—C6—P289.79 (12)C19—C17—P2—C1468.89 (11)
C2—C1—C6—P291.21 (13)C18—C17—P2—C664.08 (11)
C2—C1—N1—C50.59 (18)C19—C17—P2—C6175.49 (10)
C6—C1—N1—C5179.56 (11)C15—C14—P2—C1725.88 (12)
C4—C5—N1—C10.29 (19)C16—C14—P2—C17100.93 (11)
C7—C5—N1—C1179.40 (12)C15—C14—P2—C680.12 (11)
C1—C6—P1—C11159.59 (9)C16—C14—P2—C6153.07 (10)
P2—C6—P1—C1173.66 (7)C1—C6—P2—C1768.16 (11)
C1—C6—P1—C854.67 (10)P1—C6—P2—C17166.08 (6)
P2—C6—P1—C8178.58 (6)C1—C6—P2—C1440.00 (11)
C13—C11—P1—C661.86 (12)P1—C6—P2—C1485.77 (7)
{2-[Bis(diisopropylphosphanyl)methyl]-6-methylpyridine-κ2P,N}dichloridoiron(II) (2) top
Crystal data top
[FeCl2(C19H35NP2)]Z = 2
Mr = 466.17F(000) = 492
Triclinic, P1Dx = 1.334 Mg m3
a = 8.2907 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.7222 (2) ÅCell parameters from 9793 reflections
c = 13.6434 (2) Åθ = 2.5–30.6°
α = 87.0826 (6)°µ = 1.02 mm1
β = 80.8448 (6)°T = 150 K
γ = 75.7315 (6)°Prism, colourless
V = 1160.35 (3) Å30.40 × 0.39 × 0.35 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
5588 independent reflections
Radiation source: fine-focus sealed tube5098 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm-1Rint = 0.021
φ and ω scansθmax = 28.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
h = 1010
Tmin = 0.67, Tmax = 0.72k = 1414
32317 measured reflectionsl = 1818
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025H-atom parameters constrained
wR(F2) = 0.069 w = 1/[σ2(Fo2) + (0.0371P)2 + 0.4053P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
5588 reflectionsΔρmax = 0.35 e Å3
235 parametersΔρmin = 0.29 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2830 (2)0.40894 (16)0.94201 (12)0.0398 (4)
H1A0.30520.49180.90660.060*
H1B0.33890.42031.01100.060*
H1C0.32660.34730.90970.060*
C20.09722 (18)0.35914 (13)0.94009 (10)0.0279 (3)
C30.0266 (2)0.34565 (14)1.02632 (10)0.0345 (3)
H30.09630.36671.08840.041*
C40.1453 (2)0.30160 (14)1.02213 (10)0.0342 (3)
H40.19560.29581.08060.041*
C50.24327 (18)0.26611 (13)0.93169 (10)0.0276 (3)
H50.36190.23570.92720.033*
C60.16627 (16)0.27526 (11)0.84670 (9)0.0204 (2)
C70.26917 (15)0.22169 (12)0.74970 (9)0.0198 (2)
H70.38480.23420.74950.024*
C80.2573 (2)0.23721 (15)0.52530 (10)0.0317 (3)
H80.22880.30580.47400.038*
C90.1601 (2)0.13886 (17)0.50889 (12)0.0415 (4)
H9A0.18420.11460.43880.062*
H9B0.03910.17630.52710.062*
H9C0.19430.06230.55020.062*
C100.4472 (2)0.18484 (16)0.50054 (12)0.0386 (4)
H10A0.48520.11710.54860.058*
H10B0.50350.25460.50360.058*
H10C0.47500.14920.43350.058*
C110.30151 (17)0.44907 (13)0.63032 (10)0.0248 (3)
H110.42370.40780.61020.030*
C120.2426 (2)0.54297 (16)0.54739 (12)0.0403 (4)
H12A0.12110.57950.56310.060*
H12B0.26760.49710.48440.060*
H12C0.30170.61240.54170.060*
C130.2829 (2)0.52133 (14)0.72650 (11)0.0327 (3)
H13A0.34810.58700.71550.049*
H13B0.32480.46070.77820.049*
H13C0.16390.56280.74770.049*
C140.07401 (16)0.02296 (13)0.76490 (10)0.0256 (3)
H140.00370.09760.73190.031*
C150.00711 (18)0.02459 (14)0.87367 (11)0.0309 (3)
H15A0.12970.04300.87760.046*
H15B0.02270.09130.90870.046*
H15C0.03370.05950.90450.046*
C160.0610 (2)0.09787 (16)0.71464 (13)0.0394 (3)
H16A0.12470.17440.74620.059*
H16B0.10750.09550.64410.059*
H16C0.05740.10100.72150.059*
C170.38944 (17)0.02608 (13)0.84884 (11)0.0281 (3)
H170.31960.01860.90950.034*
C180.3967 (2)0.17053 (15)0.85773 (15)0.0419 (4)
H18A0.45600.21290.79570.063*
H18B0.28190.18300.87040.063*
H18C0.45660.20790.91270.063*
C190.56840 (19)0.00804 (17)0.83946 (15)0.0433 (4)
H19A0.61590.04050.89980.065*
H19B0.56600.08360.83060.065*
H19C0.63810.05560.78200.065*
Cl10.19909 (5)0.60518 (3)0.72287 (3)0.03626 (9)
Cl20.28430 (5)0.26938 (4)0.69474 (3)0.04066 (10)
Fe10.10739 (2)0.38971 (2)0.71724 (2)0.02406 (6)
N10.00088 (13)0.32666 (10)0.85065 (8)0.0215 (2)
P10.18512 (4)0.32060 (3)0.64470 (2)0.02016 (7)
P20.29435 (4)0.04141 (3)0.73723 (2)0.02283 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0330 (8)0.0397 (8)0.0354 (8)0.0005 (6)0.0120 (6)0.0043 (6)
C20.0331 (7)0.0208 (6)0.0247 (6)0.0041 (5)0.0062 (5)0.0020 (5)
C30.0537 (9)0.0248 (7)0.0197 (6)0.0058 (6)0.0046 (6)0.0009 (5)
C40.0575 (10)0.0271 (7)0.0208 (6)0.0124 (6)0.0117 (6)0.0016 (5)
C50.0349 (7)0.0242 (6)0.0261 (6)0.0079 (5)0.0111 (5)0.0026 (5)
C60.0248 (6)0.0170 (5)0.0199 (6)0.0065 (4)0.0028 (5)0.0014 (4)
C70.0180 (5)0.0205 (6)0.0205 (6)0.0045 (4)0.0020 (4)0.0006 (4)
C80.0402 (8)0.0357 (7)0.0187 (6)0.0097 (6)0.0010 (5)0.0030 (5)
C90.0506 (10)0.0459 (9)0.0324 (8)0.0155 (8)0.0113 (7)0.0085 (7)
C100.0406 (8)0.0375 (8)0.0341 (8)0.0119 (7)0.0126 (6)0.0124 (6)
C110.0240 (6)0.0250 (6)0.0249 (6)0.0078 (5)0.0007 (5)0.0018 (5)
C120.0507 (10)0.0376 (8)0.0347 (8)0.0170 (7)0.0072 (7)0.0144 (6)
C130.0413 (8)0.0262 (7)0.0321 (7)0.0126 (6)0.0021 (6)0.0025 (6)
C140.0229 (6)0.0263 (6)0.0296 (7)0.0082 (5)0.0072 (5)0.0009 (5)
C150.0257 (7)0.0330 (7)0.0351 (7)0.0122 (5)0.0002 (6)0.0012 (6)
C160.0456 (9)0.0380 (8)0.0408 (8)0.0188 (7)0.0101 (7)0.0039 (7)
C170.0217 (6)0.0256 (6)0.0368 (7)0.0046 (5)0.0085 (5)0.0079 (5)
C180.0365 (8)0.0270 (7)0.0618 (11)0.0061 (6)0.0134 (7)0.0134 (7)
C190.0249 (7)0.0400 (9)0.0665 (11)0.0084 (6)0.0161 (7)0.0167 (8)
Cl10.0397 (2)0.02900 (17)0.03246 (18)0.00366 (14)0.00280 (14)0.00292 (14)
Cl20.02648 (17)0.0446 (2)0.0564 (2)0.01536 (15)0.01715 (16)0.01506 (18)
Fe10.01833 (10)0.02661 (11)0.02564 (10)0.00326 (7)0.00360 (7)0.00462 (7)
N10.0223 (5)0.0195 (5)0.0207 (5)0.0041 (4)0.0012 (4)0.0010 (4)
P10.01961 (15)0.02301 (16)0.01714 (14)0.00482 (12)0.00141 (11)0.00041 (11)
P20.02126 (16)0.02019 (16)0.02495 (16)0.00324 (12)0.00002 (12)0.00049 (12)
Geometric parameters (Å, º) top
C1—C21.497 (2)C12—H12A0.9800
C1—H1A0.9800C12—H12B0.9800
C1—H1B0.9800C12—H12C0.9800
C1—H1C0.9800C13—H13A0.9800
C2—N11.3581 (16)C13—H13B0.9800
C2—C31.381 (2)C13—H13C0.9800
C3—C41.379 (2)C14—C151.528 (2)
C3—H30.9500C14—C161.531 (2)
C4—C51.379 (2)C14—P21.8628 (13)
C4—H40.9500C14—H141.0000
C5—C61.3982 (17)C15—H15A0.9800
C5—H50.9500C15—H15B0.9800
C6—N11.3527 (16)C15—H15C0.9800
C6—C71.5118 (17)C16—H16A0.9800
C7—P11.8604 (12)C16—H16B0.9800
C7—P21.9058 (12)C16—H16C0.9800
C7—H71.0000C17—C191.5276 (19)
C8—C91.521 (2)C17—C181.535 (2)
C8—C101.524 (2)C17—P21.8581 (14)
C8—P11.8401 (14)C17—H171.0000
C8—H81.0000C18—H18A0.9800
C9—H9A0.9800C18—H18B0.9800
C9—H9B0.9800C18—H18C0.9800
C9—H9C0.9800C19—H19A0.9800
C10—H10A0.9800C19—H19B0.9800
C10—H10B0.9800C19—H19C0.9800
C10—H10C0.9800Cl1—Fe12.2483 (4)
C11—C131.5252 (19)Cl2—Fe12.2420 (4)
C11—C121.533 (2)Fe1—N12.1545 (11)
C11—P11.8533 (13)Fe1—P12.4155 (4)
C11—H111.0000
C2—C1—H1A109.5H13A—C13—H13B109.5
C2—C1—H1B109.5C11—C13—H13C109.5
H1A—C1—H1B109.5H13A—C13—H13C109.5
C2—C1—H1C109.5H13B—C13—H13C109.5
H1A—C1—H1C109.5C15—C14—C16110.11 (12)
H1B—C1—H1C109.5C15—C14—P2117.72 (9)
N1—C2—C3121.21 (13)C16—C14—P2109.62 (10)
N1—C2—C1117.60 (13)C15—C14—H14106.2
C3—C2—C1121.18 (13)C16—C14—H14106.2
C4—C3—C2119.92 (13)P2—C14—H14106.2
C4—C3—H3120.0C14—C15—H15A109.5
C2—C3—H3120.0C14—C15—H15B109.5
C3—C4—C5119.01 (13)H15A—C15—H15B109.5
C3—C4—H4120.5C14—C15—H15C109.5
C5—C4—H4120.5H15A—C15—H15C109.5
C4—C5—C6119.39 (13)H15B—C15—H15C109.5
C4—C5—H5120.3C14—C16—H16A109.5
C6—C5—H5120.3C14—C16—H16B109.5
N1—C6—C5120.99 (12)H16A—C16—H16B109.5
N1—C6—C7119.20 (11)C14—C16—H16C109.5
C5—C6—C7119.75 (11)H16A—C16—H16C109.5
C6—C7—P1109.45 (8)H16B—C16—H16C109.5
C6—C7—P2113.43 (8)C19—C17—C18108.69 (12)
P1—C7—P2114.36 (6)C19—C17—P2110.00 (10)
C6—C7—H7106.3C18—C17—P2109.38 (11)
P1—C7—H7106.3C19—C17—H17109.6
P2—C7—H7106.3C18—C17—H17109.6
C9—C8—C10112.51 (13)P2—C17—H17109.6
C9—C8—P1113.87 (11)C17—C18—H18A109.5
C10—C8—P1115.03 (10)C17—C18—H18B109.5
C9—C8—H8104.7H18A—C18—H18B109.5
C10—C8—H8104.7C17—C18—H18C109.5
P1—C8—H8104.7H18A—C18—H18C109.5
C8—C9—H9A109.5H18B—C18—H18C109.5
C8—C9—H9B109.5C17—C19—H19A109.5
H9A—C9—H9B109.5C17—C19—H19B109.5
C8—C9—H9C109.5H19A—C19—H19B109.5
H9A—C9—H9C109.5C17—C19—H19C109.5
H9B—C9—H9C109.5H19A—C19—H19C109.5
C8—C10—H10A109.5H19B—C19—H19C109.5
C8—C10—H10B109.5N1—Fe1—Cl2109.28 (3)
H10A—C10—H10B109.5N1—Fe1—Cl1107.56 (3)
C8—C10—H10C109.5Cl2—Fe1—Cl1119.795 (17)
H10A—C10—H10C109.5N1—Fe1—P181.10 (3)
H10B—C10—H10C109.5Cl2—Fe1—P1118.828 (16)
C13—C11—C12110.33 (12)Cl1—Fe1—P1112.541 (15)
C13—C11—P1112.54 (9)C6—N1—C2119.21 (11)
C12—C11—P1109.83 (10)C6—N1—Fe1120.79 (8)
C13—C11—H11108.0C2—N1—Fe1119.02 (9)
C12—C11—H11108.0C8—P1—C11102.15 (6)
P1—C11—H11108.0C8—P1—C7112.31 (6)
C11—C12—H12A109.5C11—P1—C7103.01 (6)
C11—C12—H12B109.5C8—P1—Fe1123.70 (5)
H12A—C12—H12B109.5C11—P1—Fe1114.71 (4)
C11—C12—H12C109.5C7—P1—Fe199.47 (4)
H12A—C12—H12C109.5C17—P2—C14104.38 (6)
H12B—C12—H12C109.5C17—P2—C7102.68 (6)
C11—C13—H13A109.5C14—P2—C7103.41 (6)
C11—C13—H13B109.5
N1—C2—C3—C41.7 (2)C9—C8—P1—Fe139.45 (14)
C1—C2—C3—C4178.89 (14)C10—C8—P1—Fe1171.43 (9)
C2—C3—C4—C52.9 (2)C13—C11—P1—C8171.63 (10)
C3—C4—C5—C60.2 (2)C12—C11—P1—C865.03 (12)
C4—C5—C6—N14.65 (19)C13—C11—P1—C755.00 (11)
C4—C5—C6—C7172.59 (12)C12—C11—P1—C7178.34 (10)
N1—C6—C7—P134.98 (13)C13—C11—P1—Fe151.99 (11)
C5—C6—C7—P1147.74 (10)C12—C11—P1—Fe171.35 (11)
N1—C6—C7—P294.05 (12)C6—C7—P1—C8162.66 (9)
C5—C6—C7—P283.23 (13)P2—C7—P1—C834.14 (9)
C5—C6—N1—C25.90 (18)C6—C7—P1—C1188.17 (9)
C7—C6—N1—C2171.35 (11)P2—C7—P1—C11143.31 (7)
C5—C6—N1—Fe1162.68 (9)C6—C7—P1—Fe130.09 (8)
C7—C6—N1—Fe120.07 (14)P2—C7—P1—Fe198.43 (6)
C3—C2—N1—C62.74 (19)C19—C17—P2—C14175.84 (11)
C1—C2—N1—C6176.70 (12)C18—C17—P2—C1464.85 (12)
C3—C2—N1—Fe1166.04 (10)C19—C17—P2—C768.20 (12)
C1—C2—N1—Fe114.52 (16)C18—C17—P2—C7172.49 (10)
C9—C8—P1—C11170.56 (12)C15—C14—P2—C1728.56 (12)
C10—C8—P1—C1157.46 (12)C16—C14—P2—C1798.29 (11)
C9—C8—P1—C779.73 (13)C15—C14—P2—C778.54 (11)
C10—C8—P1—C752.25 (13)C16—C14—P2—C7154.61 (10)
{2-[Bis(diisopropylphosphanyl)methyl]-6-methylpyridine-κ2P,N}Dichloridocobalt(II) (3) top
Crystal data top
[CoCl2(C19H35NP2)]Z = 2
Mr = 469.25F(000) = 494
Triclinic, P1Dx = 1.351 Mg m3
a = 8.2603 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.7220 (3) ÅCell parameters from 9883 reflections
c = 13.6314 (3) Åθ = 2.5–30.6°
α = 86.8728 (10)°µ = 1.12 mm1
β = 80.5491 (10)°T = 150 K
γ = 75.6607 (10)°Prism, green
V = 1153.68 (5) Å30.23 × 0.21 × 0.09 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
5055 independent reflections
Radiation source: fine-focus sealed tube4435 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm-1Rint = 0.026
φ and ω scansθmax = 27.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
h = 1010
Tmin = 0.86, Tmax = 0.91k = 1313
27897 measured reflectionsl = 1717
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H-atom parameters constrained
wR(F2) = 0.076 w = 1/[σ2(Fo2) + (0.0382P)2 + 0.6269P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
5055 reflectionsΔρmax = 0.55 e Å3
235 parametersΔρmin = 0.27 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.1677 (2)0.27679 (16)0.84696 (12)0.0208 (3)
C20.2458 (2)0.26706 (17)0.93160 (13)0.0272 (4)
H20.36520.23700.92640.033*
C30.1482 (3)0.30144 (18)1.02277 (14)0.0335 (4)
H30.19940.29491.08100.040*
C40.0243 (3)0.34538 (18)1.02812 (13)0.0336 (4)
H40.09350.36581.09080.040*
C50.0971 (2)0.35983 (17)0.94242 (13)0.0274 (4)
C60.2698 (2)0.22339 (16)0.74928 (12)0.0199 (3)
H60.38630.23560.74820.024*
C70.2837 (3)0.4095 (2)0.94511 (15)0.0383 (5)
H7A0.30610.49150.90830.057*
H7B0.33920.42271.01430.057*
H7C0.32800.34690.91450.057*
C80.2527 (3)0.2395 (2)0.52468 (14)0.0347 (4)
H80.22300.30860.47380.042*
C90.1541 (3)0.1418 (2)0.50914 (16)0.0439 (5)
H9A0.17180.12190.43830.066*
H9B0.03330.17760.53200.066*
H9C0.19350.06300.54710.066*
C100.4436 (3)0.1875 (2)0.49794 (16)0.0408 (5)
H10A0.48320.11960.54570.061*
H10B0.50010.25740.50010.061*
H10C0.47020.15190.43090.061*
C110.2999 (2)0.45151 (17)0.62813 (13)0.0245 (4)
H110.42270.41110.60680.029*
C120.2373 (3)0.5454 (2)0.54598 (15)0.0396 (5)
H12A0.11500.58060.56290.059*
H12B0.26190.50000.48280.059*
H12C0.29490.61580.53970.059*
C130.2818 (3)0.52369 (18)0.72452 (14)0.0321 (4)
H13A0.34310.59190.71230.048*
H13B0.32890.46360.77520.048*
H13C0.16190.56190.74780.048*
C140.0730 (2)0.02547 (18)0.76461 (13)0.0255 (4)
H140.00260.10020.73150.031*
C150.0092 (2)0.02688 (19)0.87381 (14)0.0293 (4)
H15A0.13250.04820.87790.044*
H15B0.02350.09150.90930.044*
H15C0.02870.05820.90410.044*
C160.0603 (3)0.0960 (2)0.71454 (16)0.0384 (5)
H16A0.12380.17250.74640.058*
H16B0.10760.09390.64380.058*
H16C0.05870.09900.72140.058*
C170.3897 (2)0.02492 (17)0.84804 (15)0.0279 (4)
H170.32010.02020.90880.034*
C180.3956 (3)0.1691 (2)0.85759 (19)0.0423 (5)
H18A0.45530.21190.79560.063*
H18B0.28000.18090.87050.063*
H18C0.45530.20660.91270.063*
C190.5700 (3)0.0082 (2)0.83775 (19)0.0432 (5)
H19A0.61750.04060.89820.065*
H19B0.56880.08320.82810.065*
H19C0.63960.05660.78040.065*
Cl10.28472 (6)0.27594 (5)0.69677 (4)0.03956 (13)
Cl20.20196 (6)0.60031 (5)0.72356 (4)0.03555 (12)
Co10.10060 (3)0.38617 (2)0.72371 (2)0.02386 (8)
N10.00059 (18)0.32810 (13)0.85259 (10)0.0212 (3)
P10.18442 (5)0.32224 (4)0.64424 (3)0.02112 (10)
P20.29442 (6)0.04317 (4)0.73647 (3)0.02270 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0246 (8)0.0174 (8)0.0208 (8)0.0060 (6)0.0040 (6)0.0015 (6)
C20.0339 (10)0.0240 (9)0.0267 (9)0.0085 (7)0.0121 (8)0.0020 (7)
C30.0550 (13)0.0270 (10)0.0220 (9)0.0117 (9)0.0140 (8)0.0017 (7)
C40.0519 (12)0.0247 (9)0.0193 (8)0.0047 (9)0.0016 (8)0.0009 (7)
C50.0336 (10)0.0207 (9)0.0235 (9)0.0042 (7)0.0041 (7)0.0020 (7)
C60.0179 (8)0.0208 (8)0.0208 (8)0.0050 (6)0.0023 (6)0.0005 (6)
C70.0332 (11)0.0387 (11)0.0322 (10)0.0001 (9)0.0105 (8)0.0041 (8)
C80.0461 (12)0.0370 (11)0.0207 (9)0.0103 (9)0.0031 (8)0.0041 (8)
C90.0531 (14)0.0499 (13)0.0340 (11)0.0162 (11)0.0130 (10)0.0113 (10)
C100.0472 (13)0.0382 (12)0.0334 (11)0.0130 (10)0.0126 (9)0.0135 (9)
C110.0237 (8)0.0257 (9)0.0238 (8)0.0073 (7)0.0011 (7)0.0014 (7)
C120.0500 (13)0.0378 (12)0.0336 (11)0.0172 (10)0.0082 (9)0.0137 (9)
C130.0413 (11)0.0254 (9)0.0310 (10)0.0120 (8)0.0032 (8)0.0025 (7)
C140.0221 (8)0.0283 (9)0.0279 (9)0.0083 (7)0.0064 (7)0.0006 (7)
C150.0246 (9)0.0321 (10)0.0326 (10)0.0118 (8)0.0015 (7)0.0008 (8)
C160.0425 (12)0.0404 (12)0.0386 (11)0.0191 (10)0.0080 (9)0.0070 (9)
C170.0203 (8)0.0243 (9)0.0391 (10)0.0041 (7)0.0089 (7)0.0080 (7)
C180.0371 (11)0.0275 (10)0.0631 (14)0.0078 (9)0.0153 (10)0.0132 (10)
C190.0247 (10)0.0385 (12)0.0682 (15)0.0085 (9)0.0170 (10)0.0173 (11)
Cl10.0275 (2)0.0438 (3)0.0533 (3)0.0151 (2)0.0181 (2)0.0141 (2)
Cl20.0378 (3)0.0298 (2)0.0319 (2)0.00306 (19)0.00339 (19)0.00314 (18)
Co10.01964 (13)0.02728 (14)0.02385 (13)0.00427 (9)0.00474 (9)0.00413 (9)
N10.0226 (7)0.0201 (7)0.0195 (7)0.0039 (6)0.0007 (5)0.0002 (5)
P10.0223 (2)0.0230 (2)0.0181 (2)0.00505 (17)0.00417 (16)0.00036 (16)
P20.0206 (2)0.0204 (2)0.0252 (2)0.00368 (17)0.00021 (17)0.00122 (17)
Geometric parameters (Å, º) top
C1—N11.353 (2)C12—H12A0.9800
C1—C21.399 (2)C12—H12B0.9800
C1—C61.512 (2)C12—H12C0.9800
C2—C31.380 (3)C13—H13A0.9800
C2—H20.9500C13—H13B0.9800
C3—C41.377 (3)C13—H13C0.9800
C3—H30.9500C14—C151.531 (2)
C4—C51.384 (3)C14—C161.536 (3)
C4—H40.9500C14—P21.8606 (18)
C5—N11.357 (2)C14—H141.0000
C5—C71.496 (3)C15—H15A0.9800
C6—P11.8619 (17)C15—H15B0.9800
C6—P21.9069 (17)C15—H15C0.9800
C6—H61.0000C16—H16A0.9800
C7—H7A0.9800C16—H16B0.9800
C7—H7B0.9800C16—H16C0.9800
C7—H7C0.9800C17—C191.527 (3)
C8—C91.520 (3)C17—C181.534 (3)
C8—C101.526 (3)C17—P21.8580 (18)
C8—P11.8355 (19)C17—H171.0000
C8—H81.0000C18—H18A0.9800
C9—H9A0.9800C18—H18B0.9800
C9—H9B0.9800C18—H18C0.9800
C9—H9C0.9800C19—H19A0.9800
C10—H10A0.9800C19—H19B0.9800
C10—H10B0.9800C19—H19C0.9800
C10—H10C0.9800Cl1—Co12.2285 (5)
C11—C131.529 (2)Cl2—Co12.2406 (5)
C11—C121.531 (3)Co1—N12.0637 (14)
C11—P11.8528 (18)Co1—P12.3729 (5)
C11—H111.0000
N1—C1—C2120.59 (16)H13A—C13—H13B109.5
N1—C1—C6119.43 (14)C11—C13—H13C109.5
C2—C1—C6119.90 (15)H13A—C13—H13C109.5
C3—C2—C1119.48 (18)H13B—C13—H13C109.5
C3—C2—H2120.3C15—C14—C16109.93 (15)
C1—C2—H2120.3C15—C14—P2117.85 (12)
C4—C3—C2119.03 (17)C16—C14—P2109.42 (13)
C4—C3—H3120.5C15—C14—H14106.3
C2—C3—H3120.5C16—C14—H14106.3
C3—C4—C5120.15 (17)P2—C14—H14106.3
C3—C4—H4119.9C14—C15—H15A109.5
C5—C4—H4119.9C14—C15—H15B109.5
N1—C5—C4120.69 (17)H15A—C15—H15B109.5
N1—C5—C7117.64 (17)C14—C15—H15C109.5
C4—C5—C7121.66 (17)H15A—C15—H15C109.5
C1—C6—P1109.70 (11)H15B—C15—H15C109.5
C1—C6—P2113.60 (11)C14—C16—H16A109.5
P1—C6—P2113.87 (8)C14—C16—H16B109.5
C1—C6—H6106.4H16A—C16—H16B109.5
P1—C6—H6106.4C14—C16—H16C109.5
P2—C6—H6106.4H16A—C16—H16C109.5
C5—C7—H7A109.5H16B—C16—H16C109.5
C5—C7—H7B109.5C19—C17—C18108.58 (16)
H7A—C7—H7B109.5C19—C17—P2109.94 (13)
C5—C7—H7C109.5C18—C17—P2109.49 (14)
H7A—C7—H7C109.5C19—C17—H17109.6
H7B—C7—H7C109.5C18—C17—H17109.6
C9—C8—C10112.79 (18)P2—C17—H17109.6
C9—C8—P1114.32 (15)C17—C18—H18A109.5
C10—C8—P1114.60 (14)C17—C18—H18B109.5
C9—C8—H8104.6H18A—C18—H18B109.5
C10—C8—H8104.6C17—C18—H18C109.5
P1—C8—H8104.6H18A—C18—H18C109.5
C8—C9—H9A109.5H18B—C18—H18C109.5
C8—C9—H9B109.5C17—C19—H19A109.5
H9A—C9—H9B109.5C17—C19—H19B109.5
C8—C9—H9C109.5H19A—C19—H19B109.5
H9A—C9—H9C109.5C17—C19—H19C109.5
H9B—C9—H9C109.5H19A—C19—H19C109.5
C8—C10—H10A109.5H19B—C19—H19C109.5
C8—C10—H10B109.5N1—Co1—Cl1112.54 (4)
H10A—C10—H10B109.5N1—Co1—Cl2109.55 (4)
C8—C10—H10C109.5Cl1—Co1—Cl2114.29 (2)
H10A—C10—H10C109.5N1—Co1—P184.51 (4)
H10B—C10—H10C109.5Cl1—Co1—P1119.35 (2)
C13—C11—C12110.26 (16)Cl2—Co1—P1112.672 (19)
C13—C11—P1112.29 (12)C1—N1—C5119.79 (15)
C12—C11—P1109.66 (13)C1—N1—Co1119.37 (11)
C13—C11—H11108.2C5—N1—Co1120.00 (12)
C12—C11—H11108.2C8—P1—C11102.52 (9)
P1—C11—H11108.2C8—P1—C6112.90 (9)
C11—C12—H12A109.5C11—P1—C6103.39 (8)
C11—C12—H12B109.5C8—P1—Co1124.58 (7)
H12A—C12—H12B109.5C11—P1—Co1114.91 (6)
C11—C12—H12C109.5C6—P1—Co196.97 (5)
H12A—C12—H12C109.5C17—P2—C14104.43 (8)
H12B—C12—H12C109.5C17—P2—C6102.49 (8)
C11—C13—H13A109.5C14—P2—C6103.37 (8)
C11—C13—H13B109.5
N1—C1—C2—C34.8 (3)C9—C8—P1—Co137.26 (19)
C6—C1—C2—C3172.06 (16)C10—C8—P1—Co1169.67 (12)
C1—C2—C3—C40.4 (3)C13—C11—P1—C8172.22 (14)
C2—C3—C4—C52.7 (3)C12—C11—P1—C864.83 (15)
C3—C4—C5—N11.6 (3)C13—C11—P1—C654.67 (15)
C3—C4—C5—C7178.89 (18)C12—C11—P1—C6177.61 (13)
N1—C1—C6—P135.13 (18)C13—C11—P1—Co149.69 (14)
C2—C1—C6—P1148.02 (13)C12—C11—P1—Co173.25 (14)
N1—C1—C6—P293.59 (16)C1—C6—P1—C8162.06 (12)
C2—C1—C6—P283.25 (17)P2—C6—P1—C833.48 (12)
C2—C1—N1—C55.9 (2)C1—C6—P1—C1187.92 (12)
C6—C1—N1—C5170.90 (15)P2—C6—P1—C11143.51 (9)
C2—C1—N1—Co1163.58 (12)C1—C6—P1—Co129.82 (11)
C6—C1—N1—Co119.6 (2)P2—C6—P1—Co198.76 (8)
C4—C5—N1—C12.8 (3)C19—C17—P2—C14176.23 (15)
C7—C5—N1—C1176.75 (16)C18—C17—P2—C1464.56 (15)
C4—C5—N1—Co1166.68 (13)C19—C17—P2—C668.67 (16)
C7—C5—N1—Co113.8 (2)C18—C17—P2—C6172.12 (13)
C9—C8—P1—C11169.88 (16)C15—C14—P2—C1728.50 (16)
C10—C8—P1—C1157.71 (17)C16—C14—P2—C1798.02 (14)
C9—C8—P1—C679.55 (18)C15—C14—P2—C678.40 (15)
C10—C8—P1—C652.86 (17)C16—C14—P2—C6155.08 (13)
{2-[Bis(diisopropylphosphanyl)methyl]-6-methylpyridine-κ2P,P'}bromidotricarbonylmanganese(I) (4) top
Crystal data top
[MnBr(C19H35NP2)(CO)3]F(000) = 1152
Mr = 558.30Dx = 1.468 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 10.6732 (5) ÅCell parameters from 9776 reflections
b = 15.6935 (8) Åθ = 2.3–30.5°
c = 15.1651 (7) ŵ = 2.25 mm1
β = 96.0732 (8)°T = 150 K
V = 2525.9 (2) Å3Prism, yellow
Z = 40.47 × 0.45 × 0.29 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
5516 independent reflections
Radiation source: fine-focus sealed tube5115 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm-1Rint = 0.019
φ and ω scansθmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
h = 1313
Tmin = 0.47, Tmax = 0.56k = 2020
38793 measured reflectionsl = 1919
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025H-atom parameters constrained
wR(F2) = 0.066 w = 1/[σ2(Fo2) + (0.0327P)2 + 2.4763P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
5516 reflectionsΔρmax = 1.27 e Å3
280 parametersΔρmin = 1.13 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.86271 (2)0.15244 (2)0.75598 (2)0.02870 (6)
C10.76352 (15)0.31049 (11)0.91915 (11)0.0174 (3)
H10.74970.32310.85420.021*
C20.71734 (15)0.38884 (11)0.96330 (11)0.0182 (3)
C30.68219 (16)0.46122 (11)0.91389 (12)0.0220 (3)
H30.68000.46060.85110.026*
C40.65049 (17)0.53407 (12)0.95777 (14)0.0265 (4)
H40.62760.58470.92570.032*
C50.65259 (17)0.53195 (12)1.04890 (14)0.0269 (4)
H50.63320.58161.08060.032*
C60.68347 (16)0.45599 (12)1.09402 (12)0.0228 (4)
C70.6795 (2)0.44925 (15)1.19237 (13)0.0333 (4)
H7A0.59230.44091.20520.050*
H7B0.71280.50181.22090.050*
H7C0.73090.40071.21530.050*
C80.99883 (17)0.30789 (12)1.05249 (12)0.0238 (4)
H80.94120.28481.09460.029*
C91.12674 (19)0.26387 (14)1.07379 (14)0.0332 (4)
H9A1.18650.28621.03470.050*
H9B1.11680.20231.06450.050*
H9C1.15860.27491.13570.050*
C101.01451 (19)0.40360 (13)1.07148 (14)0.0313 (4)
H10A1.03380.41261.13540.047*
H10B0.93620.43341.05070.047*
H10C1.08350.42601.04050.047*
C111.02520 (19)0.34353 (12)0.86686 (13)0.0272 (4)
H111.06650.38930.90560.033*
C121.13191 (19)0.29164 (14)0.83270 (15)0.0332 (4)
H12A1.09590.24710.79230.050*
H12B1.18290.26530.88290.050*
H12C1.18500.32940.80100.050*
C130.9474 (2)0.38844 (14)0.79116 (15)0.0357 (5)
H13A1.00270.42350.75840.054*
H13B0.88450.42490.81500.054*
H13C0.90470.34600.75120.054*
C140.62604 (18)0.19279 (11)1.03665 (12)0.0236 (4)
H140.68890.21751.08330.028*
C150.6082 (2)0.09909 (13)1.06248 (14)0.0333 (4)
H15A0.59430.09581.12520.050*
H15B0.68380.06651.05250.050*
H15C0.53520.07531.02610.050*
C160.50324 (19)0.24226 (13)1.04172 (14)0.0316 (4)
H16A0.43410.21291.00640.047*
H16B0.51220.29991.01840.047*
H16C0.48490.24561.10360.047*
C170.57238 (17)0.19128 (13)0.83652 (12)0.0248 (4)
H170.61860.18670.78270.030*
C180.5001 (2)0.10751 (15)0.83992 (17)0.0398 (5)
H18A0.44570.10990.88800.060*
H18B0.55990.06030.85050.060*
H18C0.44830.09860.78340.060*
C190.48371 (19)0.26722 (14)0.81859 (15)0.0338 (5)
H19A0.43380.25980.76110.051*
H19B0.53320.31970.81780.051*
H19C0.42720.27090.86540.051*
C201.05195 (18)0.10106 (11)0.91269 (11)0.0231 (4)
C210.90914 (17)0.11645 (11)1.03912 (12)0.0231 (4)
C220.82297 (18)0.02603 (12)0.90060 (12)0.0265 (4)
Mn10.88897 (2)0.13251 (2)0.92200 (2)0.01672 (7)
N10.71680 (14)0.38578 (9)1.05191 (10)0.0204 (3)
O11.15471 (13)0.08261 (9)0.90860 (10)0.0323 (3)
O20.92268 (15)0.10661 (9)1.11372 (9)0.0319 (3)
O30.78116 (16)0.04005 (9)0.88575 (11)0.0414 (4)
P10.93236 (4)0.27707 (3)0.93926 (3)0.01703 (9)
P20.69669 (4)0.20131 (3)0.93074 (3)0.01628 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02552 (10)0.04377 (12)0.01665 (9)0.00896 (8)0.00157 (7)0.00067 (7)
C10.0176 (7)0.0164 (8)0.0182 (7)0.0011 (6)0.0023 (6)0.0023 (6)
C20.0143 (7)0.0169 (8)0.0235 (8)0.0002 (6)0.0026 (6)0.0001 (6)
C30.0182 (8)0.0207 (8)0.0276 (9)0.0019 (6)0.0046 (7)0.0043 (7)
C40.0206 (8)0.0178 (8)0.0419 (11)0.0024 (7)0.0066 (8)0.0052 (8)
C50.0199 (8)0.0207 (9)0.0411 (11)0.0001 (7)0.0082 (7)0.0073 (8)
C60.0157 (8)0.0255 (9)0.0275 (9)0.0033 (7)0.0043 (7)0.0059 (7)
C70.0319 (10)0.0400 (12)0.0285 (10)0.0005 (9)0.0054 (8)0.0085 (9)
C80.0249 (9)0.0226 (9)0.0231 (8)0.0032 (7)0.0010 (7)0.0033 (7)
C90.0294 (10)0.0336 (11)0.0336 (10)0.0018 (8)0.0116 (8)0.0055 (8)
C100.0300 (10)0.0246 (10)0.0391 (11)0.0069 (8)0.0027 (8)0.0087 (8)
C110.0276 (9)0.0251 (9)0.0308 (10)0.0024 (7)0.0117 (8)0.0032 (7)
C120.0234 (9)0.0364 (11)0.0422 (12)0.0015 (8)0.0143 (8)0.0052 (9)
C130.0399 (12)0.0344 (11)0.0361 (11)0.0085 (9)0.0196 (9)0.0133 (9)
C140.0299 (9)0.0204 (9)0.0223 (8)0.0018 (7)0.0114 (7)0.0012 (7)
C150.0451 (12)0.0228 (10)0.0350 (10)0.0046 (8)0.0183 (9)0.0034 (8)
C160.0311 (10)0.0292 (10)0.0375 (11)0.0005 (8)0.0180 (8)0.0041 (8)
C170.0178 (8)0.0312 (10)0.0248 (9)0.0018 (7)0.0006 (7)0.0054 (7)
C180.0294 (11)0.0354 (12)0.0529 (14)0.0051 (9)0.0041 (9)0.0149 (10)
C190.0230 (9)0.0397 (12)0.0371 (11)0.0074 (8)0.0049 (8)0.0009 (9)
C200.0287 (9)0.0202 (8)0.0196 (8)0.0043 (7)0.0013 (7)0.0001 (7)
C210.0258 (9)0.0152 (8)0.0276 (9)0.0008 (7)0.0011 (7)0.0008 (7)
C220.0278 (9)0.0239 (9)0.0260 (9)0.0063 (7)0.0052 (7)0.0019 (7)
Mn10.01885 (13)0.01605 (13)0.01478 (12)0.00353 (9)0.00050 (9)0.00087 (9)
N10.0188 (7)0.0206 (7)0.0219 (7)0.0003 (6)0.0029 (5)0.0002 (6)
O10.0248 (7)0.0337 (8)0.0383 (8)0.0106 (6)0.0031 (6)0.0014 (6)
O20.0471 (9)0.0270 (7)0.0209 (7)0.0013 (6)0.0008 (6)0.0008 (5)
O30.0465 (9)0.0214 (7)0.0525 (10)0.0018 (6)0.0119 (7)0.0063 (7)
P10.01598 (19)0.0173 (2)0.0180 (2)0.00095 (15)0.00251 (15)0.00128 (15)
P20.0167 (2)0.0154 (2)0.01706 (19)0.00041 (15)0.00292 (15)0.00067 (15)
Geometric parameters (Å, º) top
Br1—Mn12.5231 (3)C12—H12B0.9800
C1—C21.508 (2)C12—H12C0.9800
C1—P11.8707 (17)C13—H13A0.9800
C1—P21.8715 (17)C13—H13B0.9800
C1—H11.0000C13—H13C0.9800
C2—N11.345 (2)C14—C161.532 (3)
C2—C31.390 (2)C14—C151.539 (3)
C3—C41.383 (3)C14—P21.8500 (17)
C3—H30.9500C14—H141.0000
C4—C51.380 (3)C15—H15A0.9800
C4—H40.9500C15—H15B0.9800
C5—C61.397 (3)C15—H15C0.9800
C5—H50.9500C16—H16A0.9800
C6—N11.340 (2)C16—H16B0.9800
C6—C71.500 (3)C16—H16C0.9800
C7—H7A0.9800C17—C181.528 (3)
C7—H7B0.9800C17—C191.528 (3)
C7—H7C0.9800C17—P21.8509 (18)
C8—C91.534 (3)C17—H171.0000
C8—C101.535 (3)C18—H18A0.9800
C8—P11.8515 (18)C18—H18B0.9800
C8—H81.0000C18—H18C0.9800
C9—H9A0.9800C19—H19A0.9800
C9—H9B0.9800C19—H19B0.9800
C9—H9C0.9800C19—H19C0.9800
C10—H10A0.9800C20—O11.142 (2)
C10—H10B0.9800C20—Mn11.8279 (19)
C10—H10C0.9800C21—O21.136 (2)
C11—C131.517 (3)C21—Mn11.7842 (19)
C11—C121.534 (3)C22—O31.142 (2)
C11—P11.8724 (19)C22—Mn11.829 (2)
C11—H111.0000Mn1—P12.3247 (5)
C12—H12A0.9800Mn1—P22.3351 (5)
C2—C1—P1120.72 (12)C15—C14—P2111.27 (13)
C2—C1—P2124.01 (12)C16—C14—H14106.4
P1—C1—P295.63 (8)C15—C14—H14106.4
C2—C1—H1104.8P2—C14—H14106.4
P1—C1—H1104.8C14—C15—H15A109.5
P2—C1—H1104.8C14—C15—H15B109.5
N1—C2—C3122.55 (16)H15A—C15—H15B109.5
N1—C2—C1116.79 (15)C14—C15—H15C109.5
C3—C2—C1120.62 (15)H15A—C15—H15C109.5
C4—C3—C2118.82 (17)H15B—C15—H15C109.5
C4—C3—H3120.6C14—C16—H16A109.5
C2—C3—H3120.6C14—C16—H16B109.5
C5—C4—C3118.89 (17)H16A—C16—H16B109.5
C5—C4—H4120.6C14—C16—H16C109.5
C3—C4—H4120.6H16A—C16—H16C109.5
C4—C5—C6119.28 (17)H16B—C16—H16C109.5
C4—C5—H5120.4C18—C17—C19111.81 (16)
C6—C5—H5120.4C18—C17—P2111.74 (14)
N1—C6—C5121.94 (17)C19—C17—P2116.80 (14)
N1—C6—C7116.91 (17)C18—C17—H17105.1
C5—C6—C7121.15 (17)C19—C17—H17105.1
C6—C7—H7A109.5P2—C17—H17105.1
C6—C7—H7B109.5C17—C18—H18A109.5
H7A—C7—H7B109.5C17—C18—H18B109.5
C6—C7—H7C109.5H18A—C18—H18B109.5
H7A—C7—H7C109.5C17—C18—H18C109.5
H7B—C7—H7C109.5H18A—C18—H18C109.5
C9—C8—C10108.92 (16)H18B—C18—H18C109.5
C9—C8—P1108.84 (13)C17—C19—H19A109.5
C10—C8—P1116.94 (14)C17—C19—H19B109.5
C9—C8—H8107.2H19A—C19—H19B109.5
C10—C8—H8107.2C17—C19—H19C109.5
P1—C8—H8107.2H19A—C19—H19C109.5
C8—C9—H9A109.5H19B—C19—H19C109.5
C8—C9—H9B109.5O1—C20—Mn1178.35 (17)
H9A—C9—H9B109.5O2—C21—Mn1179.51 (19)
C8—C9—H9C109.5O3—C22—Mn1178.81 (18)
H9A—C9—H9C109.5C21—Mn1—C2091.33 (8)
H9B—C9—H9C109.5C21—Mn1—C2292.94 (8)
C8—C10—H10A109.5C20—Mn1—C2295.24 (8)
C8—C10—H10B109.5C21—Mn1—P191.38 (6)
H10A—C10—H10B109.5C20—Mn1—P195.30 (6)
C8—C10—H10C109.5C22—Mn1—P1168.51 (6)
H10A—C10—H10C109.5C21—Mn1—P291.32 (6)
H10B—C10—H10C109.5C20—Mn1—P2168.09 (6)
C13—C11—C12110.95 (17)C22—Mn1—P296.21 (6)
C13—C11—P1114.91 (14)P1—Mn1—P273.032 (17)
C12—C11—P1111.11 (13)C21—Mn1—Br1178.86 (6)
C13—C11—H11106.4C20—Mn1—Br187.86 (6)
C12—C11—H11106.4C22—Mn1—Br186.34 (6)
P1—C11—H11106.4P1—Mn1—Br189.492 (14)
C11—C12—H12A109.5P2—Mn1—Br189.641 (14)
C11—C12—H12B109.5C6—N1—C2118.43 (15)
H12A—C12—H12B109.5C8—P1—C1110.24 (8)
C11—C12—H12C109.5C8—P1—C11102.93 (9)
H12A—C12—H12C109.5C1—P1—C11107.98 (8)
H12B—C12—H12C109.5C8—P1—Mn1114.31 (6)
C11—C13—H13A109.5C1—P1—Mn194.49 (5)
C11—C13—H13B109.5C11—P1—Mn1126.09 (7)
H13A—C13—H13B109.5C14—P2—C17109.84 (9)
C11—C13—H13C109.5C14—P2—C1110.00 (8)
H13A—C13—H13C109.5C17—P2—C1104.75 (8)
H13B—C13—H13C109.5C14—P2—Mn1117.21 (6)
C16—C14—C15109.99 (16)C17—P2—Mn1118.65 (6)
C16—C14—P2115.87 (13)C1—P2—Mn194.13 (5)
P1—C1—C2—N167.21 (18)P2—C1—P1—Mn113.67 (6)
P2—C1—C2—N155.4 (2)C13—C11—P1—C8133.76 (16)
P1—C1—C2—C3110.34 (16)C12—C11—P1—C899.24 (16)
P2—C1—C2—C3127.07 (15)C13—C11—P1—C117.17 (17)
N1—C2—C3—C42.8 (3)C12—C11—P1—C1144.17 (15)
C1—C2—C3—C4174.63 (15)C13—C11—P1—Mn192.61 (15)
C2—C3—C4—C51.2 (3)C12—C11—P1—Mn134.39 (18)
C3—C4—C5—C61.6 (3)C16—C14—P2—C1743.55 (17)
C4—C5—C6—N13.1 (3)C15—C14—P2—C1783.07 (16)
C4—C5—C6—C7176.34 (17)C16—C14—P2—C171.24 (16)
C5—C6—N1—C21.6 (3)C15—C14—P2—C1162.14 (14)
C7—C6—N1—C2177.88 (16)C16—C14—P2—Mn1177.11 (12)
C3—C2—N1—C61.4 (2)C15—C14—P2—Mn156.27 (16)
C1—C2—N1—C6176.10 (15)C18—C17—P2—C1457.39 (16)
C9—C8—P1—C1168.34 (13)C19—C17—P2—C1473.12 (17)
C10—C8—P1—C167.77 (16)C18—C17—P2—C1175.49 (14)
C9—C8—P1—C1176.69 (15)C19—C17—P2—C144.98 (17)
C10—C8—P1—C1147.20 (16)C18—C17—P2—Mn181.29 (15)
C9—C8—P1—Mn163.38 (14)C19—C17—P2—Mn1148.20 (13)
C10—C8—P1—Mn1172.72 (12)C2—C1—P2—C1425.96 (16)
C2—C1—P1—C831.12 (16)P1—C1—P2—C14107.34 (9)
P2—C1—P1—C8104.30 (9)C2—C1—P2—C1792.03 (15)
C2—C1—P1—C1180.61 (15)P1—C1—P2—C17134.67 (8)
P2—C1—P1—C11143.97 (8)C2—C1—P2—Mn1146.90 (13)
C2—C1—P1—Mn1149.09 (12)P1—C1—P2—Mn113.60 (6)
Selected bond lengths for complexes 2, 3 and 4 top
234
M—N2.155?(1)2.064?(1)
M—P12.4155?(4)2.3729 (5)2.3247 (5)
M—P22.3351 (5)
M—X2.2483 (4), 2.2420 (4)2.2285 (5), 2.2406 (5)2.5231 (3)
For complex 2, M = Fe, X = Cl; for complex 3, M = Co, X = Cl; for complex 4, M = Mn, X = Br.
 

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