Synthesis and coordination chemistry of the PPN ligand 2-[bis­(diiso­propyl­phosphanyl)methyl]-6-methyl­pyridine

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.

Computing details

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)

Crystal data

C19H35NP2	F(000) = 744
Mr = 339.42	Dx = 1.095 Mg m^−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.2905 (5) Å	Cell parameters from 9990 reflections
b = 6.7510 (2) Å	θ = 2.4–30.4°
c = 18.9112 (6) Å	µ = 0.21 mm^−1
β = 98.2024 (11)°	T = 150 K
V = 2058.52 (11) Å^3	Prism, colourless
Z = 4	0.38 × 0.16 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	4970 independent reflections
Radiation source: fine-focus sealed tube	4231 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm^-1	Rint = 0.032
φ and ω scans	θmax = 28.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −21→21
Tmin = 0.93, Tmax = 0.98	k = −8→8
37883 measured reflections	l = −24→24

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.035	H-atom parameters constrained
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.0487P)^2 + 0.9053P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
4970 reflections	Δρmax = 0.69 e Å^−3
208 parameters	Δρmin = −0.21 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.77919 (8)	0.8830 (2)	0.42774 (6)	0.0213 (3)
C2	0.78860 (8)	1.0883 (2)	0.42979 (7)	0.0259 (3)
H2	0.7535	1.1705	0.3978	0.031*
C3	0.84985 (9)	1.1701 (2)	0.47916 (8)	0.0317 (3)
H3	0.8572	1.3096	0.4820	0.038*
C4	0.90014 (9)	1.0459 (2)	0.52422 (8)	0.0322 (3)
H4	0.9432	1.0989	0.5581	0.039*
C5	0.88726 (8)	0.8429 (2)	0.51961 (7)	0.0272 (3)
C6	0.71201 (8)	0.79161 (19)	0.37513 (6)	0.0205 (2)
H6	0.6660	0.8904	0.3657	0.025*
C7	0.93883 (10)	0.7011 (3)	0.56840 (8)	0.0392 (4)
H7A	0.9024	0.6169	0.5925	0.059*
H7B	0.9761	0.7757	0.6041	0.059*
H7C	0.9717	0.6182	0.5404	0.059*
C8	0.63311 (8)	0.6310 (2)	0.49637 (7)	0.0263 (3)
H8	0.5758	0.5761	0.4944	0.032*
C9	0.62598 (10)	0.8512 (2)	0.51338 (8)	0.0337 (3)
H9A	0.5963	0.8669	0.5546	0.051*
H9B	0.5955	0.9193	0.4720	0.051*
H9C	0.6816	0.9085	0.5245	0.051*
C10	0.68569 (10)	0.5220 (3)	0.55748 (8)	0.0396 (4)
H10A	0.7424	0.5741	0.5635	0.059*
H10B	0.6866	0.3803	0.5465	0.059*
H10C	0.6619	0.5417	0.6017	0.059*
C11	0.56638 (8)	0.5504 (2)	0.34873 (7)	0.0260 (3)
H11	0.5798	0.5473	0.2988	0.031*
C12	0.52500 (10)	0.3524 (3)	0.36082 (9)	0.0381 (4)
H12A	0.5089	0.3503	0.4088	0.057*
H12B	0.5640	0.2442	0.3563	0.057*
H12C	0.4756	0.3358	0.3251	0.057*
C13	0.50540 (9)	0.7204 (3)	0.35190 (9)	0.0376 (4)
H13A	0.4558	0.6973	0.3170	0.056*
H13B	0.5315	0.8451	0.3407	0.056*
H13C	0.4897	0.7280	0.4000	0.056*
C14	0.85088 (8)	0.6208 (2)	0.31272 (7)	0.0256 (3)
H14	0.8488	0.5425	0.3573	0.031*
C15	0.92280 (9)	0.7664 (2)	0.32984 (8)	0.0314 (3)
H15A	0.9737	0.6933	0.3472	0.047*
H15B	0.9104	0.8593	0.3667	0.047*
H15C	0.9304	0.8399	0.2866	0.047*
C16	0.87039 (10)	0.4719 (2)	0.25599 (9)	0.0381 (4)
H16A	0.8771	0.5427	0.2119	0.057*
H16B	0.8247	0.3767	0.2462	0.057*
H16C	0.9218	0.4011	0.2736	0.057*
C17	0.76112 (9)	0.9705 (2)	0.24781 (7)	0.0257 (3)
H17	0.8024	1.0457	0.2818	0.031*
C18	0.67987 (10)	1.0874 (3)	0.23489 (9)	0.0372 (4)
H18A	0.6889	1.2120	0.2106	0.056*
H18B	0.6610	1.1159	0.2808	0.056*
H18C	0.6377	1.0090	0.2050	0.056*
C19	0.79489 (11)	0.9447 (3)	0.17675 (8)	0.0371 (4)
H19A	0.7558	0.8658	0.1440	0.056*
H19B	0.8486	0.8767	0.1852	0.056*
H19C	0.8019	1.0750	0.1556	0.056*
N1	0.82729 (7)	0.76162 (17)	0.47200 (6)	0.0230 (2)
P1	0.66772 (2)	0.56127 (5)	0.40902 (2)	0.02128 (9)
P2	0.74421 (2)	0.72323 (5)	0.28634 (2)	0.02138 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0207 (6)	0.0257 (7)	0.0190 (5)	−0.0024 (5)	0.0079 (5)	−0.0024 (5)
C2	0.0270 (6)	0.0248 (7)	0.0270 (6)	−0.0011 (5)	0.0075 (5)	−0.0031 (5)
C3	0.0339 (7)	0.0291 (7)	0.0340 (7)	−0.0081 (6)	0.0108 (6)	−0.0097 (6)
C4	0.0275 (7)	0.0435 (9)	0.0259 (7)	−0.0111 (6)	0.0048 (5)	−0.0104 (6)
C5	0.0222 (6)	0.0402 (8)	0.0200 (6)	−0.0025 (6)	0.0058 (5)	−0.0011 (6)
C6	0.0196 (6)	0.0219 (6)	0.0203 (6)	−0.0008 (5)	0.0039 (4)	0.0004 (5)
C7	0.0305 (8)	0.0552 (11)	0.0300 (7)	−0.0010 (7)	−0.0025 (6)	0.0066 (7)
C8	0.0263 (6)	0.0316 (7)	0.0224 (6)	−0.0041 (6)	0.0081 (5)	−0.0002 (5)
C9	0.0359 (8)	0.0377 (8)	0.0300 (7)	−0.0036 (7)	0.0131 (6)	−0.0061 (6)
C10	0.0408 (9)	0.0524 (10)	0.0265 (7)	−0.0007 (8)	0.0082 (6)	0.0084 (7)
C11	0.0234 (6)	0.0307 (7)	0.0242 (6)	−0.0068 (5)	0.0044 (5)	−0.0035 (5)
C12	0.0350 (8)	0.0373 (9)	0.0443 (9)	−0.0146 (7)	0.0140 (7)	−0.0091 (7)
C13	0.0248 (7)	0.0416 (9)	0.0437 (9)	0.0005 (6)	−0.0043 (6)	−0.0007 (7)
C14	0.0242 (6)	0.0282 (7)	0.0255 (6)	0.0003 (5)	0.0069 (5)	−0.0004 (5)
C15	0.0226 (6)	0.0414 (9)	0.0306 (7)	−0.0023 (6)	0.0050 (5)	−0.0055 (6)
C16	0.0385 (8)	0.0335 (8)	0.0449 (9)	0.0005 (7)	0.0148 (7)	−0.0100 (7)
C17	0.0289 (7)	0.0277 (7)	0.0205 (6)	−0.0052 (5)	0.0032 (5)	0.0030 (5)
C18	0.0357 (8)	0.0386 (9)	0.0365 (8)	0.0018 (7)	0.0027 (6)	0.0130 (7)
C19	0.0481 (9)	0.0409 (9)	0.0239 (7)	−0.0063 (7)	0.0106 (6)	0.0054 (6)
N1	0.0217 (5)	0.0288 (6)	0.0194 (5)	−0.0025 (4)	0.0055 (4)	0.0002 (4)
P1	0.02202 (17)	0.02089 (17)	0.02170 (16)	−0.00085 (12)	0.00575 (12)	0.00117 (12)
P2	0.02138 (17)	0.02478 (18)	0.01823 (16)	−0.00447 (13)	0.00370 (12)	−0.00078 (12)

Geometric parameters (Å, º)

C1—N1	1.3413 (17)	C11—P1	1.8691 (14)
C1—C2	1.3943 (19)	C11—H11	1.0000
C1—C6	1.5025 (17)	C12—H12A	0.9800
C2—C3	1.3807 (19)	C12—H12B	0.9800
C2—H2	0.9500	C12—H12C	0.9800
C3—C4	1.379 (2)	C13—H13A	0.9800
C3—H3	0.9500	C13—H13B	0.9800
C4—C5	1.387 (2)	C13—H13C	0.9800
C4—H4	0.9500	C14—C15	1.528 (2)
C5—N1	1.3473 (17)	C14—C16	1.536 (2)
C5—C7	1.501 (2)	C14—P2	1.8708 (14)
C6—P1	1.8659 (13)	C14—H14	1.0000
C6—P2	1.8866 (13)	C15—H15A	0.9800
C6—H6	1.0000	C15—H15B	0.9800
C7—H7A	0.9800	C15—H15C	0.9800
C7—H7B	0.9800	C16—H16A	0.9800
C7—H7C	0.9800	C16—H16B	0.9800
C8—C10	1.526 (2)	C16—H16C	0.9800
C8—C9	1.529 (2)	C17—C18	1.530 (2)
C8—P1	1.8799 (13)	C17—C19	1.5330 (19)
C8—H8	1.0000	C17—P2	1.8575 (14)
C9—H9A	0.9800	C17—H17	1.0000
C9—H9B	0.9800	C18—H18A	0.9800
C9—H9C	0.9800	C18—H18B	0.9800
C10—H10A	0.9800	C18—H18C	0.9800
C10—H10B	0.9800	C19—H19A	0.9800
C10—H10C	0.9800	C19—H19B	0.9800
C11—C13	1.525 (2)	C19—H19C	0.9800
C11—C12	1.529 (2)
N1—C1—C2	122.54 (12)	H12A—C12—H12B	109.5
N1—C1—C6	117.89 (12)	C11—C12—H12C	109.5
C2—C1—C6	119.56 (12)	H12A—C12—H12C	109.5
C3—C2—C1	118.83 (13)	H12B—C12—H12C	109.5
C3—C2—H2	120.6	C11—C13—H13A	109.5
C1—C2—H2	120.6	C11—C13—H13B	109.5
C4—C3—C2	118.90 (14)	H13A—C13—H13B	109.5
C4—C3—H3	120.6	C11—C13—H13C	109.5
C2—C3—H3	120.6	H13A—C13—H13C	109.5
C3—C4—C5	119.37 (13)	H13B—C13—H13C	109.5
C3—C4—H4	120.3	C15—C14—C16	109.89 (11)
C5—C4—H4	120.3	C15—C14—P2	118.26 (10)
N1—C5—C4	122.23 (13)	C16—C14—P2	109.43 (10)
N1—C5—C7	116.09 (14)	C15—C14—H14	106.2
C4—C5—C7	121.68 (13)	C16—C14—H14	106.2
C1—C6—P1	113.30 (9)	P2—C14—H14	106.2
C1—C6—P2	114.91 (8)	C14—C15—H15A	109.5
P1—C6—P2	105.79 (6)	C14—C15—H15B	109.5
C1—C6—H6	107.5	H15A—C15—H15B	109.5
P1—C6—H6	107.5	C14—C15—H15C	109.5
P2—C6—H6	107.5	H15A—C15—H15C	109.5
C5—C7—H7A	109.5	H15B—C15—H15C	109.5
C5—C7—H7B	109.5	C14—C16—H16A	109.5
H7A—C7—H7B	109.5	C14—C16—H16B	109.5
C5—C7—H7C	109.5	H16A—C16—H16B	109.5
H7A—C7—H7C	109.5	C14—C16—H16C	109.5
H7B—C7—H7C	109.5	H16A—C16—H16C	109.5
C10—C8—C9	111.15 (13)	H16B—C16—H16C	109.5
C10—C8—P1	109.78 (10)	C18—C17—C19	109.21 (12)
C9—C8—P1	118.01 (10)	C18—C17—P2	110.66 (10)
C10—C8—H8	105.7	C19—C17—P2	109.49 (10)
C9—C8—H8	105.7	C18—C17—H17	109.2
P1—C8—H8	105.7	C19—C17—H17	109.2
C8—C9—H9A	109.5	P2—C17—H17	109.2
C8—C9—H9B	109.5	C17—C18—H18A	109.5
H9A—C9—H9B	109.5	C17—C18—H18B	109.5
C8—C9—H9C	109.5	H18A—C18—H18B	109.5
H9A—C9—H9C	109.5	C17—C18—H18C	109.5
H9B—C9—H9C	109.5	H18A—C18—H18C	109.5
C8—C10—H10A	109.5	H18B—C18—H18C	109.5
C8—C10—H10B	109.5	C17—C19—H19A	109.5
H10A—C10—H10B	109.5	C17—C19—H19B	109.5
C8—C10—H10C	109.5	H19A—C19—H19B	109.5
H10A—C10—H10C	109.5	C17—C19—H19C	109.5
H10B—C10—H10C	109.5	H19A—C19—H19C	109.5
C13—C11—C12	110.40 (12)	H19B—C19—H19C	109.5
C13—C11—P1	118.04 (10)	C1—N1—C5	118.13 (12)
C12—C11—P1	108.25 (10)	C6—P1—C11	100.05 (6)
C13—C11—H11	106.5	C6—P1—C8	105.80 (6)
C12—C11—H11	106.5	C11—P1—C8	101.32 (6)
P1—C11—H11	106.5	C17—P2—C14	104.64 (6)
C11—C12—H12A	109.5	C17—P2—C6	101.82 (6)
C11—C12—H12B	109.5	C14—P2—C6	102.64 (6)
N1—C1—C2—C3	0.1 (2)	C12—C11—P1—C6	171.88 (10)
C6—C1—C2—C3	179.06 (11)	C13—C11—P1—C8	46.65 (12)
C1—C2—C3—C4	0.7 (2)	C12—C11—P1—C8	−79.61 (11)
C2—C3—C4—C5	−0.9 (2)	C10—C8—P1—C6	−113.91 (11)
C3—C4—C5—N1	0.5 (2)	C9—C8—P1—C6	14.81 (12)
C3—C4—C5—C7	−178.59 (13)	C10—C8—P1—C11	142.11 (11)
N1—C1—C6—P1	31.99 (14)	C9—C8—P1—C11	−89.17 (12)
C2—C1—C6—P1	−147.01 (10)	C18—C17—P2—C14	−170.68 (10)
N1—C1—C6—P2	−89.79 (12)	C19—C17—P2—C14	68.89 (11)
C2—C1—C6—P2	91.21 (13)	C18—C17—P2—C6	−64.08 (11)
C2—C1—N1—C5	−0.59 (18)	C19—C17—P2—C6	175.49 (10)
C6—C1—N1—C5	−179.56 (11)	C15—C14—P2—C17	25.88 (12)
C4—C5—N1—C1	0.29 (19)	C16—C14—P2—C17	−100.93 (11)
C7—C5—N1—C1	179.40 (12)	C15—C14—P2—C6	−80.12 (11)
C1—C6—P1—C11	159.59 (9)	C16—C14—P2—C6	153.07 (10)
P2—C6—P1—C11	−73.66 (7)	C1—C6—P2—C17	−68.16 (11)
C1—C6—P1—C8	54.67 (10)	P1—C6—P2—C17	166.08 (6)
P2—C6—P1—C8	−178.58 (6)	C1—C6—P2—C14	40.00 (11)
C13—C11—P1—C6	−61.86 (12)	P1—C6—P2—C14	−85.77 (7)

{2-[Bis(diisopropylphosphanyl)methyl]-6-methylpyridine-κ²P,N}dichloridoiron(II) (2)

Crystal data

[FeCl2(C19H35NP2)]	Z = 2
Mr = 466.17	F(000) = 492
Triclinic, P1	Dx = 1.334 Mg m^−3
a = 8.2907 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7222 (2) Å	Cell parameters from 9793 reflections
c = 13.6434 (2) Å	θ = 2.5–30.6°
α = 87.0826 (6)°	µ = 1.02 mm^−1
β = 80.8448 (6)°	T = 150 K
γ = 75.7315 (6)°	Prism, colourless
V = 1160.35 (3) Å^3	0.40 × 0.39 × 0.35 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	5588 independent reflections
Radiation source: fine-focus sealed tube	5098 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm^-1	Rint = 0.021
φ and ω scans	θmax = 28.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −10→10
Tmin = 0.67, Tmax = 0.72	k = −14→14
32317 measured reflections	l = −18→18

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.025	H-atom parameters constrained
wR(F^2) = 0.069	w = 1/[σ^2(Fo^2) + (0.0371P)^2 + 0.4053P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
5588 reflections	Δρmax = 0.35 e Å^−3
235 parameters	Δρmin = −0.29 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.2830 (2)	0.40894 (16)	0.94201 (12)	0.0398 (4)
H1A	−0.3052	0.4918	0.9066	0.060*
H1B	−0.3389	0.4203	1.0110	0.060*
H1C	−0.3266	0.3473	0.9097	0.060*
C2	−0.09722 (18)	0.35914 (13)	0.94009 (10)	0.0279 (3)
C3	−0.0266 (2)	0.34565 (14)	1.02632 (10)	0.0345 (3)
H3	−0.0963	0.3667	1.0884	0.041*
C4	0.1453 (2)	0.30160 (14)	1.02213 (10)	0.0342 (3)
H4	0.1956	0.2958	1.0806	0.041*
C5	0.24327 (18)	0.26611 (13)	0.93169 (10)	0.0276 (3)
H5	0.3619	0.2357	0.9272	0.033*
C6	0.16627 (16)	0.27526 (11)	0.84670 (9)	0.0204 (2)
C7	0.26917 (15)	0.22169 (12)	0.74970 (9)	0.0198 (2)
H7	0.3848	0.2342	0.7495	0.024*
C8	0.2573 (2)	0.23721 (15)	0.52530 (10)	0.0317 (3)
H8	0.2288	0.3058	0.4740	0.038*
C9	0.1601 (2)	0.13886 (17)	0.50889 (12)	0.0415 (4)
H9A	0.1842	0.1146	0.4388	0.062*
H9B	0.0391	0.1763	0.5271	0.062*
H9C	0.1943	0.0623	0.5502	0.062*
C10	0.4472 (2)	0.18484 (16)	0.50054 (12)	0.0386 (4)
H10A	0.4852	0.1171	0.5486	0.058*
H10B	0.5035	0.2546	0.5036	0.058*
H10C	0.4750	0.1492	0.4335	0.058*
C11	0.30151 (17)	0.44907 (13)	0.63032 (10)	0.0248 (3)
H11	0.4237	0.4078	0.6102	0.030*
C12	0.2426 (2)	0.54297 (16)	0.54739 (12)	0.0403 (4)
H12A	0.1211	0.5795	0.5631	0.060*
H12B	0.2676	0.4971	0.4844	0.060*
H12C	0.3017	0.6124	0.5417	0.060*
C13	0.2829 (2)	0.52133 (14)	0.72650 (11)	0.0327 (3)
H13A	0.3481	0.5870	0.7155	0.049*
H13B	0.3248	0.4607	0.7782	0.049*
H13C	0.1639	0.5628	0.7477	0.049*
C14	0.07401 (16)	0.02296 (13)	0.76490 (10)	0.0256 (3)
H14	0.0037	0.0976	0.7319	0.031*
C15	−0.00711 (18)	0.02459 (14)	0.87367 (11)	0.0309 (3)
H15A	−0.1297	0.0430	0.8776	0.046*
H15B	0.0227	0.0913	0.9087	0.046*
H15C	0.0337	−0.0595	0.9045	0.046*
C16	0.0610 (2)	−0.09787 (16)	0.71464 (13)	0.0394 (3)
H16A	0.1247	−0.1744	0.7462	0.059*
H16B	0.1075	−0.0955	0.6441	0.059*
H16C	−0.0574	−0.1010	0.7215	0.059*
C17	0.38944 (17)	−0.02608 (13)	0.84884 (11)	0.0281 (3)
H17	0.3196	0.0186	0.9095	0.034*
C18	0.3967 (2)	−0.17053 (15)	0.85773 (15)	0.0419 (4)
H18A	0.4560	−0.2129	0.7957	0.063*
H18B	0.2819	−0.1830	0.8704	0.063*
H18C	0.4566	−0.2079	0.9127	0.063*
C19	0.56840 (19)	−0.00804 (17)	0.83946 (15)	0.0433 (4)
H19A	0.6159	−0.0405	0.8998	0.065*
H19B	0.5660	0.0836	0.8306	0.065*
H19C	0.6381	−0.0556	0.7820	0.065*
Cl1	−0.19909 (5)	0.60518 (3)	0.72287 (3)	0.03626 (9)
Cl2	−0.28430 (5)	0.26938 (4)	0.69474 (3)	0.04066 (10)
Fe1	−0.10739 (2)	0.38971 (2)	0.71724 (2)	0.02406 (6)
N1	−0.00088 (13)	0.32666 (10)	0.85065 (8)	0.0215 (2)
P1	0.18512 (4)	0.32060 (3)	0.64470 (2)	0.02016 (7)
P2	0.29435 (4)	0.04141 (3)	0.73723 (2)	0.02283 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0330 (8)	0.0397 (8)	0.0354 (8)	0.0005 (6)	0.0120 (6)	0.0043 (6)
C2	0.0331 (7)	0.0208 (6)	0.0247 (6)	−0.0041 (5)	0.0062 (5)	0.0020 (5)
C3	0.0537 (9)	0.0248 (7)	0.0197 (6)	−0.0058 (6)	0.0046 (6)	−0.0009 (5)
C4	0.0575 (10)	0.0271 (7)	0.0208 (6)	−0.0124 (6)	−0.0117 (6)	0.0016 (5)
C5	0.0349 (7)	0.0242 (6)	0.0261 (6)	−0.0079 (5)	−0.0111 (5)	0.0026 (5)
C6	0.0248 (6)	0.0170 (5)	0.0199 (6)	−0.0065 (4)	−0.0028 (5)	0.0014 (4)
C7	0.0180 (5)	0.0205 (6)	0.0205 (6)	−0.0045 (4)	−0.0020 (4)	0.0006 (4)
C8	0.0402 (8)	0.0357 (7)	0.0187 (6)	−0.0097 (6)	−0.0010 (5)	−0.0030 (5)
C9	0.0506 (10)	0.0459 (9)	0.0324 (8)	−0.0155 (8)	−0.0113 (7)	−0.0085 (7)
C10	0.0406 (8)	0.0375 (8)	0.0341 (8)	−0.0119 (7)	0.0126 (6)	−0.0124 (6)
C11	0.0240 (6)	0.0250 (6)	0.0249 (6)	−0.0078 (5)	0.0007 (5)	0.0018 (5)
C12	0.0507 (10)	0.0376 (8)	0.0347 (8)	−0.0170 (7)	−0.0072 (7)	0.0144 (6)
C13	0.0413 (8)	0.0262 (7)	0.0321 (7)	−0.0126 (6)	−0.0021 (6)	−0.0025 (6)
C14	0.0229 (6)	0.0263 (6)	0.0296 (7)	−0.0082 (5)	−0.0072 (5)	0.0009 (5)
C15	0.0257 (7)	0.0330 (7)	0.0351 (7)	−0.0122 (5)	−0.0002 (6)	0.0012 (6)
C16	0.0456 (9)	0.0380 (8)	0.0408 (8)	−0.0188 (7)	−0.0101 (7)	−0.0039 (7)
C17	0.0217 (6)	0.0256 (6)	0.0368 (7)	−0.0046 (5)	−0.0085 (5)	0.0079 (5)
C18	0.0365 (8)	0.0270 (7)	0.0618 (11)	−0.0061 (6)	−0.0134 (7)	0.0134 (7)
C19	0.0249 (7)	0.0400 (9)	0.0665 (11)	−0.0084 (6)	−0.0161 (7)	0.0167 (8)
Cl1	0.0397 (2)	0.02900 (17)	0.03246 (18)	0.00366 (14)	−0.00280 (14)	0.00292 (14)
Cl2	0.02648 (17)	0.0446 (2)	0.0564 (2)	−0.01536 (15)	−0.01715 (16)	0.01506 (18)
Fe1	0.01833 (10)	0.02661 (11)	0.02564 (10)	−0.00326 (7)	−0.00360 (7)	0.00462 (7)
N1	0.0223 (5)	0.0195 (5)	0.0207 (5)	−0.0041 (4)	0.0012 (4)	0.0010 (4)
P1	0.01961 (15)	0.02301 (16)	0.01714 (14)	−0.00482 (12)	−0.00141 (11)	0.00041 (11)
P2	0.02126 (16)	0.02019 (16)	0.02495 (16)	−0.00324 (12)	−0.00002 (12)	−0.00049 (12)

Geometric parameters (Å, º)

C1—C2	1.497 (2)	C12—H12A	0.9800
C1—H1A	0.9800	C12—H12B	0.9800
C1—H1B	0.9800	C12—H12C	0.9800
C1—H1C	0.9800	C13—H13A	0.9800
C2—N1	1.3581 (16)	C13—H13B	0.9800
C2—C3	1.381 (2)	C13—H13C	0.9800
C3—C4	1.379 (2)	C14—C15	1.528 (2)
C3—H3	0.9500	C14—C16	1.531 (2)
C4—C5	1.379 (2)	C14—P2	1.8628 (13)
C4—H4	0.9500	C14—H14	1.0000
C5—C6	1.3982 (17)	C15—H15A	0.9800
C5—H5	0.9500	C15—H15B	0.9800
C6—N1	1.3527 (16)	C15—H15C	0.9800
C6—C7	1.5118 (17)	C16—H16A	0.9800
C7—P1	1.8604 (12)	C16—H16B	0.9800
C7—P2	1.9058 (12)	C16—H16C	0.9800
C7—H7	1.0000	C17—C19	1.5276 (19)
C8—C9	1.521 (2)	C17—C18	1.535 (2)
C8—C10	1.524 (2)	C17—P2	1.8581 (14)
C8—P1	1.8401 (14)	C17—H17	1.0000
C8—H8	1.0000	C18—H18A	0.9800
C9—H9A	0.9800	C18—H18B	0.9800
C9—H9B	0.9800	C18—H18C	0.9800
C9—H9C	0.9800	C19—H19A	0.9800
C10—H10A	0.9800	C19—H19B	0.9800
C10—H10B	0.9800	C19—H19C	0.9800
C10—H10C	0.9800	Cl1—Fe1	2.2483 (4)
C11—C13	1.5252 (19)	Cl2—Fe1	2.2420 (4)
C11—C12	1.533 (2)	Fe1—N1	2.1545 (11)
C11—P1	1.8533 (13)	Fe1—P1	2.4155 (4)
C11—H11	1.0000
C2—C1—H1A	109.5	H13A—C13—H13B	109.5
C2—C1—H1B	109.5	C11—C13—H13C	109.5
H1A—C1—H1B	109.5	H13A—C13—H13C	109.5
C2—C1—H1C	109.5	H13B—C13—H13C	109.5
H1A—C1—H1C	109.5	C15—C14—C16	110.11 (12)
H1B—C1—H1C	109.5	C15—C14—P2	117.72 (9)
N1—C2—C3	121.21 (13)	C16—C14—P2	109.62 (10)
N1—C2—C1	117.60 (13)	C15—C14—H14	106.2
C3—C2—C1	121.18 (13)	C16—C14—H14	106.2
C4—C3—C2	119.92 (13)	P2—C14—H14	106.2
C4—C3—H3	120.0	C14—C15—H15A	109.5
C2—C3—H3	120.0	C14—C15—H15B	109.5
C3—C4—C5	119.01 (13)	H15A—C15—H15B	109.5
C3—C4—H4	120.5	C14—C15—H15C	109.5
C5—C4—H4	120.5	H15A—C15—H15C	109.5
C4—C5—C6	119.39 (13)	H15B—C15—H15C	109.5
C4—C5—H5	120.3	C14—C16—H16A	109.5
C6—C5—H5	120.3	C14—C16—H16B	109.5
N1—C6—C5	120.99 (12)	H16A—C16—H16B	109.5
N1—C6—C7	119.20 (11)	C14—C16—H16C	109.5
C5—C6—C7	119.75 (11)	H16A—C16—H16C	109.5
C6—C7—P1	109.45 (8)	H16B—C16—H16C	109.5
C6—C7—P2	113.43 (8)	C19—C17—C18	108.69 (12)
P1—C7—P2	114.36 (6)	C19—C17—P2	110.00 (10)
C6—C7—H7	106.3	C18—C17—P2	109.38 (11)
P1—C7—H7	106.3	C19—C17—H17	109.6
P2—C7—H7	106.3	C18—C17—H17	109.6
C9—C8—C10	112.51 (13)	P2—C17—H17	109.6
C9—C8—P1	113.87 (11)	C17—C18—H18A	109.5
C10—C8—P1	115.03 (10)	C17—C18—H18B	109.5
C9—C8—H8	104.7	H18A—C18—H18B	109.5
C10—C8—H8	104.7	C17—C18—H18C	109.5
P1—C8—H8	104.7	H18A—C18—H18C	109.5
C8—C9—H9A	109.5	H18B—C18—H18C	109.5
C8—C9—H9B	109.5	C17—C19—H19A	109.5
H9A—C9—H9B	109.5	C17—C19—H19B	109.5
C8—C9—H9C	109.5	H19A—C19—H19B	109.5
H9A—C9—H9C	109.5	C17—C19—H19C	109.5
H9B—C9—H9C	109.5	H19A—C19—H19C	109.5
C8—C10—H10A	109.5	H19B—C19—H19C	109.5
C8—C10—H10B	109.5	N1—Fe1—Cl2	109.28 (3)
H10A—C10—H10B	109.5	N1—Fe1—Cl1	107.56 (3)
C8—C10—H10C	109.5	Cl2—Fe1—Cl1	119.795 (17)
H10A—C10—H10C	109.5	N1—Fe1—P1	81.10 (3)
H10B—C10—H10C	109.5	Cl2—Fe1—P1	118.828 (16)
C13—C11—C12	110.33 (12)	Cl1—Fe1—P1	112.541 (15)
C13—C11—P1	112.54 (9)	C6—N1—C2	119.21 (11)
C12—C11—P1	109.83 (10)	C6—N1—Fe1	120.79 (8)
C13—C11—H11	108.0	C2—N1—Fe1	119.02 (9)
C12—C11—H11	108.0	C8—P1—C11	102.15 (6)
P1—C11—H11	108.0	C8—P1—C7	112.31 (6)
C11—C12—H12A	109.5	C11—P1—C7	103.01 (6)
C11—C12—H12B	109.5	C8—P1—Fe1	123.70 (5)
H12A—C12—H12B	109.5	C11—P1—Fe1	114.71 (4)
C11—C12—H12C	109.5	C7—P1—Fe1	99.47 (4)
H12A—C12—H12C	109.5	C17—P2—C14	104.38 (6)
H12B—C12—H12C	109.5	C17—P2—C7	102.68 (6)
C11—C13—H13A	109.5	C14—P2—C7	103.41 (6)
C11—C13—H13B	109.5
N1—C2—C3—C4	1.7 (2)	C9—C8—P1—Fe1	−39.45 (14)
C1—C2—C3—C4	−178.89 (14)	C10—C8—P1—Fe1	−171.43 (9)
C2—C3—C4—C5	−2.9 (2)	C13—C11—P1—C8	−171.63 (10)
C3—C4—C5—C6	−0.2 (2)	C12—C11—P1—C8	65.03 (12)
C4—C5—C6—N1	4.65 (19)	C13—C11—P1—C7	−55.00 (11)
C4—C5—C6—C7	−172.59 (12)	C12—C11—P1—C7	−178.34 (10)
N1—C6—C7—P1	34.98 (13)	C13—C11—P1—Fe1	51.99 (11)
C5—C6—C7—P1	−147.74 (10)	C12—C11—P1—Fe1	−71.35 (11)
N1—C6—C7—P2	−94.05 (12)	C6—C7—P1—C8	−162.66 (9)
C5—C6—C7—P2	83.23 (13)	P2—C7—P1—C8	−34.14 (9)
C5—C6—N1—C2	−5.90 (18)	C6—C7—P1—C11	88.17 (9)
C7—C6—N1—C2	171.35 (11)	P2—C7—P1—C11	−143.31 (7)
C5—C6—N1—Fe1	162.68 (9)	C6—C7—P1—Fe1	−30.09 (8)
C7—C6—N1—Fe1	−20.07 (14)	P2—C7—P1—Fe1	98.43 (6)
C3—C2—N1—C6	2.74 (19)	C19—C17—P2—C14	−175.84 (11)
C1—C2—N1—C6	−176.70 (12)	C18—C17—P2—C14	64.85 (12)
C3—C2—N1—Fe1	−166.04 (10)	C19—C17—P2—C7	−68.20 (12)
C1—C2—N1—Fe1	14.52 (16)	C18—C17—P2—C7	172.49 (10)
C9—C8—P1—C11	−170.56 (12)	C15—C14—P2—C17	28.56 (12)
C10—C8—P1—C11	57.46 (12)	C16—C14—P2—C17	−98.29 (11)
C9—C8—P1—C7	79.73 (13)	C15—C14—P2—C7	−78.54 (11)
C10—C8—P1—C7	−52.25 (13)	C16—C14—P2—C7	154.61 (10)

{2-[Bis(diisopropylphosphanyl)methyl]-6-methylpyridine-κ²P,N}Dichloridocobalt(II) (3)

Crystal data

[CoCl2(C19H35NP2)]	Z = 2
Mr = 469.25	F(000) = 494
Triclinic, P1	Dx = 1.351 Mg m^−3
a = 8.2603 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7220 (3) Å	Cell parameters from 9883 reflections
c = 13.6314 (3) Å	θ = 2.5–30.6°
α = 86.8728 (10)°	µ = 1.12 mm^−1
β = 80.5491 (10)°	T = 150 K
γ = 75.6607 (10)°	Prism, green
V = 1153.68 (5) Å^3	0.23 × 0.21 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	5055 independent reflections
Radiation source: fine-focus sealed tube	4435 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm^-1	Rint = 0.026
φ and ω scans	θmax = 27.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −10→10
Tmin = 0.86, Tmax = 0.91	k = −13→13
27897 measured reflections	l = −17→17

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.029	H-atom parameters constrained
wR(F^2) = 0.076	w = 1/[σ^2(Fo^2) + (0.0382P)^2 + 0.6269P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
5055 reflections	Δρmax = 0.55 e Å^−3
235 parameters	Δρmin = −0.27 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1677 (2)	0.27679 (16)	0.84696 (12)	0.0208 (3)
C2	0.2458 (2)	0.26706 (17)	0.93160 (13)	0.0272 (4)
H2	0.3652	0.2370	0.9264	0.033*
C3	0.1482 (3)	0.30144 (18)	1.02277 (14)	0.0335 (4)
H3	0.1994	0.2949	1.0810	0.040*
C4	−0.0243 (3)	0.34538 (18)	1.02812 (13)	0.0336 (4)
H4	−0.0935	0.3658	1.0908	0.040*
C5	−0.0971 (2)	0.35983 (17)	0.94242 (13)	0.0274 (4)
C6	0.2698 (2)	0.22339 (16)	0.74928 (12)	0.0199 (3)
H6	0.3863	0.2356	0.7482	0.024*
C7	−0.2837 (3)	0.4095 (2)	0.94511 (15)	0.0383 (5)
H7A	−0.3061	0.4915	0.9083	0.057*
H7B	−0.3392	0.4227	1.0143	0.057*
H7C	−0.3280	0.3469	0.9145	0.057*
C8	0.2527 (3)	0.2395 (2)	0.52468 (14)	0.0347 (4)
H8	0.2230	0.3086	0.4738	0.042*
C9	0.1541 (3)	0.1418 (2)	0.50914 (16)	0.0439 (5)
H9A	0.1718	0.1219	0.4383	0.066*
H9B	0.0333	0.1776	0.5320	0.066*
H9C	0.1935	0.0630	0.5471	0.066*
C10	0.4436 (3)	0.1875 (2)	0.49794 (16)	0.0408 (5)
H10A	0.4832	0.1196	0.5457	0.061*
H10B	0.5001	0.2574	0.5001	0.061*
H10C	0.4702	0.1519	0.4309	0.061*
C11	0.2999 (2)	0.45151 (17)	0.62813 (13)	0.0245 (4)
H11	0.4227	0.4111	0.6068	0.029*
C12	0.2373 (3)	0.5454 (2)	0.54598 (15)	0.0396 (5)
H12A	0.1150	0.5806	0.5629	0.059*
H12B	0.2619	0.5000	0.4828	0.059*
H12C	0.2949	0.6158	0.5397	0.059*
C13	0.2818 (3)	0.52369 (18)	0.72452 (14)	0.0321 (4)
H13A	0.3431	0.5919	0.7123	0.048*
H13B	0.3289	0.4636	0.7752	0.048*
H13C	0.1619	0.5619	0.7478	0.048*
C14	0.0730 (2)	0.02547 (18)	0.76461 (13)	0.0255 (4)
H14	0.0026	0.1002	0.7315	0.031*
C15	−0.0092 (2)	0.02688 (19)	0.87381 (14)	0.0293 (4)
H15A	−0.1325	0.0482	0.8779	0.044*
H15B	0.0235	0.0915	0.9093	0.044*
H15C	0.0287	−0.0582	0.9041	0.044*
C16	0.0603 (3)	−0.0960 (2)	0.71454 (16)	0.0384 (5)
H16A	0.1238	−0.1725	0.7464	0.058*
H16B	0.1076	−0.0939	0.6438	0.058*
H16C	−0.0587	−0.0990	0.7214	0.058*
C17	0.3897 (2)	−0.02492 (17)	0.84804 (15)	0.0279 (4)
H17	0.3201	0.0202	0.9088	0.034*
C18	0.3956 (3)	−0.1691 (2)	0.85759 (19)	0.0423 (5)
H18A	0.4553	−0.2119	0.7956	0.063*
H18B	0.2800	−0.1809	0.8705	0.063*
H18C	0.4553	−0.2066	0.9127	0.063*
C19	0.5700 (3)	−0.0082 (2)	0.83775 (19)	0.0432 (5)
H19A	0.6175	−0.0406	0.8982	0.065*
H19B	0.5688	0.0832	0.8281	0.065*
H19C	0.6396	−0.0566	0.7804	0.065*
Cl1	−0.28472 (6)	0.27594 (5)	0.69677 (4)	0.03956 (13)
Cl2	−0.20196 (6)	0.60031 (5)	0.72356 (4)	0.03555 (12)
Co1	−0.10060 (3)	0.38617 (2)	0.72371 (2)	0.02386 (8)
N1	−0.00059 (18)	0.32810 (13)	0.85259 (10)	0.0212 (3)
P1	0.18442 (5)	0.32224 (4)	0.64424 (3)	0.02112 (10)
P2	0.29442 (6)	0.04317 (4)	0.73647 (3)	0.02270 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0246 (8)	0.0174 (8)	0.0208 (8)	−0.0060 (6)	−0.0040 (6)	0.0015 (6)
C2	0.0339 (10)	0.0240 (9)	0.0267 (9)	−0.0085 (7)	−0.0121 (8)	0.0020 (7)
C3	0.0550 (13)	0.0270 (10)	0.0220 (9)	−0.0117 (9)	−0.0140 (8)	0.0017 (7)
C4	0.0519 (12)	0.0247 (9)	0.0193 (8)	−0.0047 (9)	0.0016 (8)	−0.0009 (7)
C5	0.0336 (10)	0.0207 (9)	0.0235 (9)	−0.0042 (7)	0.0041 (7)	0.0020 (7)
C6	0.0179 (8)	0.0208 (8)	0.0208 (8)	−0.0050 (6)	−0.0023 (6)	0.0005 (6)
C7	0.0332 (11)	0.0387 (11)	0.0322 (10)	0.0001 (9)	0.0105 (8)	0.0041 (8)
C8	0.0461 (12)	0.0370 (11)	0.0207 (9)	−0.0103 (9)	−0.0031 (8)	−0.0041 (8)
C9	0.0531 (14)	0.0499 (13)	0.0340 (11)	−0.0162 (11)	−0.0130 (10)	−0.0113 (10)
C10	0.0472 (13)	0.0382 (12)	0.0334 (11)	−0.0130 (10)	0.0126 (9)	−0.0135 (9)
C11	0.0237 (8)	0.0257 (9)	0.0238 (8)	−0.0073 (7)	−0.0011 (7)	0.0014 (7)
C12	0.0500 (13)	0.0378 (12)	0.0336 (11)	−0.0172 (10)	−0.0082 (9)	0.0137 (9)
C13	0.0413 (11)	0.0254 (9)	0.0310 (10)	−0.0120 (8)	−0.0032 (8)	−0.0025 (7)
C14	0.0221 (8)	0.0283 (9)	0.0279 (9)	−0.0083 (7)	−0.0064 (7)	0.0006 (7)
C15	0.0246 (9)	0.0321 (10)	0.0326 (10)	−0.0118 (8)	−0.0015 (7)	0.0008 (8)
C16	0.0425 (12)	0.0404 (12)	0.0386 (11)	−0.0191 (10)	−0.0080 (9)	−0.0070 (9)
C17	0.0203 (8)	0.0243 (9)	0.0391 (10)	−0.0041 (7)	−0.0089 (7)	0.0080 (7)
C18	0.0371 (11)	0.0275 (10)	0.0631 (14)	−0.0078 (9)	−0.0153 (10)	0.0132 (10)
C19	0.0247 (10)	0.0385 (12)	0.0682 (15)	−0.0085 (9)	−0.0170 (10)	0.0173 (11)
Cl1	0.0275 (2)	0.0438 (3)	0.0533 (3)	−0.0151 (2)	−0.0181 (2)	0.0141 (2)
Cl2	0.0378 (3)	0.0298 (2)	0.0319 (2)	0.00306 (19)	−0.00339 (19)	0.00314 (18)
Co1	0.01964 (13)	0.02728 (14)	0.02385 (13)	−0.00427 (9)	−0.00474 (9)	0.00413 (9)
N1	0.0226 (7)	0.0201 (7)	0.0195 (7)	−0.0039 (6)	−0.0007 (5)	0.0002 (5)
P1	0.0223 (2)	0.0230 (2)	0.0181 (2)	−0.00505 (17)	−0.00417 (16)	0.00036 (16)
P2	0.0206 (2)	0.0204 (2)	0.0252 (2)	−0.00368 (17)	0.00021 (17)	−0.00122 (17)

Geometric parameters (Å, º)

C1—N1	1.353 (2)	C12—H12A	0.9800
C1—C2	1.399 (2)	C12—H12B	0.9800
C1—C6	1.512 (2)	C12—H12C	0.9800
C2—C3	1.380 (3)	C13—H13A	0.9800
C2—H2	0.9500	C13—H13B	0.9800
C3—C4	1.377 (3)	C13—H13C	0.9800
C3—H3	0.9500	C14—C15	1.531 (2)
C4—C5	1.384 (3)	C14—C16	1.536 (3)
C4—H4	0.9500	C14—P2	1.8606 (18)
C5—N1	1.357 (2)	C14—H14	1.0000
C5—C7	1.496 (3)	C15—H15A	0.9800
C6—P1	1.8619 (17)	C15—H15B	0.9800
C6—P2	1.9069 (17)	C15—H15C	0.9800
C6—H6	1.0000	C16—H16A	0.9800
C7—H7A	0.9800	C16—H16B	0.9800
C7—H7B	0.9800	C16—H16C	0.9800
C7—H7C	0.9800	C17—C19	1.527 (3)
C8—C9	1.520 (3)	C17—C18	1.534 (3)
C8—C10	1.526 (3)	C17—P2	1.8580 (18)
C8—P1	1.8355 (19)	C17—H17	1.0000
C8—H8	1.0000	C18—H18A	0.9800
C9—H9A	0.9800	C18—H18B	0.9800
C9—H9B	0.9800	C18—H18C	0.9800
C9—H9C	0.9800	C19—H19A	0.9800
C10—H10A	0.9800	C19—H19B	0.9800
C10—H10B	0.9800	C19—H19C	0.9800
C10—H10C	0.9800	Cl1—Co1	2.2285 (5)
C11—C13	1.529 (2)	Cl2—Co1	2.2406 (5)
C11—C12	1.531 (3)	Co1—N1	2.0637 (14)
C11—P1	1.8528 (18)	Co1—P1	2.3729 (5)
C11—H11	1.0000
N1—C1—C2	120.59 (16)	H13A—C13—H13B	109.5
N1—C1—C6	119.43 (14)	C11—C13—H13C	109.5
C2—C1—C6	119.90 (15)	H13A—C13—H13C	109.5
C3—C2—C1	119.48 (18)	H13B—C13—H13C	109.5
C3—C2—H2	120.3	C15—C14—C16	109.93 (15)
C1—C2—H2	120.3	C15—C14—P2	117.85 (12)
C4—C3—C2	119.03 (17)	C16—C14—P2	109.42 (13)
C4—C3—H3	120.5	C15—C14—H14	106.3
C2—C3—H3	120.5	C16—C14—H14	106.3
C3—C4—C5	120.15 (17)	P2—C14—H14	106.3
C3—C4—H4	119.9	C14—C15—H15A	109.5
C5—C4—H4	119.9	C14—C15—H15B	109.5
N1—C5—C4	120.69 (17)	H15A—C15—H15B	109.5
N1—C5—C7	117.64 (17)	C14—C15—H15C	109.5
C4—C5—C7	121.66 (17)	H15A—C15—H15C	109.5
C1—C6—P1	109.70 (11)	H15B—C15—H15C	109.5
C1—C6—P2	113.60 (11)	C14—C16—H16A	109.5
P1—C6—P2	113.87 (8)	C14—C16—H16B	109.5
C1—C6—H6	106.4	H16A—C16—H16B	109.5
P1—C6—H6	106.4	C14—C16—H16C	109.5
P2—C6—H6	106.4	H16A—C16—H16C	109.5
C5—C7—H7A	109.5	H16B—C16—H16C	109.5
C5—C7—H7B	109.5	C19—C17—C18	108.58 (16)
H7A—C7—H7B	109.5	C19—C17—P2	109.94 (13)
C5—C7—H7C	109.5	C18—C17—P2	109.49 (14)
H7A—C7—H7C	109.5	C19—C17—H17	109.6
H7B—C7—H7C	109.5	C18—C17—H17	109.6
C9—C8—C10	112.79 (18)	P2—C17—H17	109.6
C9—C8—P1	114.32 (15)	C17—C18—H18A	109.5
C10—C8—P1	114.60 (14)	C17—C18—H18B	109.5
C9—C8—H8	104.6	H18A—C18—H18B	109.5
C10—C8—H8	104.6	C17—C18—H18C	109.5
P1—C8—H8	104.6	H18A—C18—H18C	109.5
C8—C9—H9A	109.5	H18B—C18—H18C	109.5
C8—C9—H9B	109.5	C17—C19—H19A	109.5
H9A—C9—H9B	109.5	C17—C19—H19B	109.5
C8—C9—H9C	109.5	H19A—C19—H19B	109.5
H9A—C9—H9C	109.5	C17—C19—H19C	109.5
H9B—C9—H9C	109.5	H19A—C19—H19C	109.5
C8—C10—H10A	109.5	H19B—C19—H19C	109.5
C8—C10—H10B	109.5	N1—Co1—Cl1	112.54 (4)
H10A—C10—H10B	109.5	N1—Co1—Cl2	109.55 (4)
C8—C10—H10C	109.5	Cl1—Co1—Cl2	114.29 (2)
H10A—C10—H10C	109.5	N1—Co1—P1	84.51 (4)
H10B—C10—H10C	109.5	Cl1—Co1—P1	119.35 (2)
C13—C11—C12	110.26 (16)	Cl2—Co1—P1	112.672 (19)
C13—C11—P1	112.29 (12)	C1—N1—C5	119.79 (15)
C12—C11—P1	109.66 (13)	C1—N1—Co1	119.37 (11)
C13—C11—H11	108.2	C5—N1—Co1	120.00 (12)
C12—C11—H11	108.2	C8—P1—C11	102.52 (9)
P1—C11—H11	108.2	C8—P1—C6	112.90 (9)
C11—C12—H12A	109.5	C11—P1—C6	103.39 (8)
C11—C12—H12B	109.5	C8—P1—Co1	124.58 (7)
H12A—C12—H12B	109.5	C11—P1—Co1	114.91 (6)
C11—C12—H12C	109.5	C6—P1—Co1	96.97 (5)
H12A—C12—H12C	109.5	C17—P2—C14	104.43 (8)
H12B—C12—H12C	109.5	C17—P2—C6	102.49 (8)
C11—C13—H13A	109.5	C14—P2—C6	103.37 (8)
C11—C13—H13B	109.5
N1—C1—C2—C3	4.8 (3)	C9—C8—P1—Co1	−37.26 (19)
C6—C1—C2—C3	−172.06 (16)	C10—C8—P1—Co1	−169.67 (12)
C1—C2—C3—C4	−0.4 (3)	C13—C11—P1—C8	−172.22 (14)
C2—C3—C4—C5	−2.7 (3)	C12—C11—P1—C8	64.83 (15)
C3—C4—C5—N1	1.6 (3)	C13—C11—P1—C6	−54.67 (15)
C3—C4—C5—C7	−178.89 (18)	C12—C11—P1—C6	−177.61 (13)
N1—C1—C6—P1	35.13 (18)	C13—C11—P1—Co1	49.69 (14)
C2—C1—C6—P1	−148.02 (13)	C12—C11—P1—Co1	−73.25 (14)
N1—C1—C6—P2	−93.59 (16)	C1—C6—P1—C8	−162.06 (12)
C2—C1—C6—P2	83.25 (17)	P2—C6—P1—C8	−33.48 (12)
C2—C1—N1—C5	−5.9 (2)	C1—C6—P1—C11	87.92 (12)
C6—C1—N1—C5	170.90 (15)	P2—C6—P1—C11	−143.51 (9)
C2—C1—N1—Co1	163.58 (12)	C1—C6—P1—Co1	−29.82 (11)
C6—C1—N1—Co1	−19.6 (2)	P2—C6—P1—Co1	98.76 (8)
C4—C5—N1—C1	2.8 (3)	C19—C17—P2—C14	−176.23 (15)
C7—C5—N1—C1	−176.75 (16)	C18—C17—P2—C14	64.56 (15)
C4—C5—N1—Co1	−166.68 (13)	C19—C17—P2—C6	−68.67 (16)
C7—C5—N1—Co1	13.8 (2)	C18—C17—P2—C6	172.12 (13)
C9—C8—P1—C11	−169.88 (16)	C15—C14—P2—C17	28.50 (16)
C10—C8—P1—C11	57.71 (17)	C16—C14—P2—C17	−98.02 (14)
C9—C8—P1—C6	79.55 (18)	C15—C14—P2—C6	−78.40 (15)
C10—C8—P1—C6	−52.86 (17)	C16—C14—P2—C6	155.08 (13)

{2-[Bis(diisopropylphosphanyl)methyl]-6-methylpyridine-κ²P,P'}bromidotricarbonylmanganese(I) (4)

Crystal data

[MnBr(C19H35NP2)(CO)3]	F(000) = 1152
Mr = 558.30	Dx = 1.468 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.6732 (5) Å	Cell parameters from 9776 reflections
b = 15.6935 (8) Å	θ = 2.3–30.5°
c = 15.1651 (7) Å	µ = 2.25 mm^−1
β = 96.0732 (8)°	T = 150 K
V = 2525.9 (2) Å^3	Prism, yellow
Z = 4	0.47 × 0.45 × 0.29 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	5516 independent reflections
Radiation source: fine-focus sealed tube	5115 reflections with I > 2σ(I)
Detector resolution: 8.3333 pixels mm^-1	Rint = 0.019
φ and ω scans	θmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −13→13
Tmin = 0.47, Tmax = 0.56	k = −20→20
38793 measured reflections	l = −19→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.025	H-atom parameters constrained
wR(F^2) = 0.066	w = 1/[σ^2(Fo^2) + (0.0327P)^2 + 2.4763P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
5516 reflections	Δρmax = 1.27 e Å^−3
280 parameters	Δρmin = −1.13 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.86271 (2)	0.15244 (2)	0.75598 (2)	0.02870 (6)
C1	0.76352 (15)	0.31049 (11)	0.91915 (11)	0.0174 (3)
H1	0.7497	0.3231	0.8542	0.021*
C2	0.71734 (15)	0.38884 (11)	0.96330 (11)	0.0182 (3)
C3	0.68219 (16)	0.46122 (11)	0.91389 (12)	0.0220 (3)
H3	0.6800	0.4606	0.8511	0.026*
C4	0.65049 (17)	0.53407 (12)	0.95777 (14)	0.0265 (4)
H4	0.6276	0.5847	0.9257	0.032*
C5	0.65259 (17)	0.53195 (12)	1.04890 (14)	0.0269 (4)
H5	0.6332	0.5816	1.0806	0.032*
C6	0.68347 (16)	0.45599 (12)	1.09402 (12)	0.0228 (4)
C7	0.6795 (2)	0.44925 (15)	1.19237 (13)	0.0333 (4)
H7A	0.5923	0.4409	1.2052	0.050*
H7B	0.7128	0.5018	1.2209	0.050*
H7C	0.7309	0.4007	1.2153	0.050*
C8	0.99883 (17)	0.30789 (12)	1.05249 (12)	0.0238 (4)
H8	0.9412	0.2848	1.0946	0.029*
C9	1.12674 (19)	0.26387 (14)	1.07379 (14)	0.0332 (4)
H9A	1.1865	0.2862	1.0347	0.050*
H9B	1.1168	0.2023	1.0645	0.050*
H9C	1.1586	0.2749	1.1357	0.050*
C10	1.01451 (19)	0.40360 (13)	1.07148 (14)	0.0313 (4)
H10A	1.0338	0.4126	1.1354	0.047*
H10B	0.9362	0.4334	1.0507	0.047*
H10C	1.0835	0.4260	1.0405	0.047*
C11	1.02520 (19)	0.34353 (12)	0.86686 (13)	0.0272 (4)
H11	1.0665	0.3893	0.9056	0.033*
C12	1.13191 (19)	0.29164 (14)	0.83270 (15)	0.0332 (4)
H12A	1.0959	0.2471	0.7923	0.050*
H12B	1.1829	0.2653	0.8829	0.050*
H12C	1.1850	0.3294	0.8010	0.050*
C13	0.9474 (2)	0.38844 (14)	0.79116 (15)	0.0357 (5)
H13A	1.0027	0.4235	0.7584	0.054*
H13B	0.8845	0.4249	0.8150	0.054*
H13C	0.9047	0.3460	0.7512	0.054*
C14	0.62604 (18)	0.19279 (11)	1.03665 (12)	0.0236 (4)
H14	0.6889	0.2175	1.0833	0.028*
C15	0.6082 (2)	0.09909 (13)	1.06248 (14)	0.0333 (4)
H15A	0.5943	0.0958	1.1252	0.050*
H15B	0.6838	0.0665	1.0525	0.050*
H15C	0.5352	0.0753	1.0261	0.050*
C16	0.50324 (19)	0.24226 (13)	1.04172 (14)	0.0316 (4)
H16A	0.4341	0.2129	1.0064	0.047*
H16B	0.5122	0.2999	1.0184	0.047*
H16C	0.4849	0.2456	1.1036	0.047*
C17	0.57238 (17)	0.19128 (13)	0.83652 (12)	0.0248 (4)
H17	0.6186	0.1867	0.7827	0.030*
C18	0.5001 (2)	0.10751 (15)	0.83992 (17)	0.0398 (5)
H18A	0.4457	0.1099	0.8880	0.060*
H18B	0.5599	0.0603	0.8505	0.060*
H18C	0.4483	0.0986	0.7834	0.060*
C19	0.48371 (19)	0.26722 (14)	0.81859 (15)	0.0338 (5)
H19A	0.4338	0.2598	0.7611	0.051*
H19B	0.5332	0.3197	0.8178	0.051*
H19C	0.4272	0.2709	0.8654	0.051*
C20	1.05195 (18)	0.10106 (11)	0.91269 (11)	0.0231 (4)
C21	0.90914 (17)	0.11645 (11)	1.03912 (12)	0.0231 (4)
C22	0.82297 (18)	0.02603 (12)	0.90060 (12)	0.0265 (4)
Mn1	0.88897 (2)	0.13251 (2)	0.92200 (2)	0.01672 (7)
N1	0.71680 (14)	0.38578 (9)	1.05191 (10)	0.0204 (3)
O1	1.15471 (13)	0.08261 (9)	0.90860 (10)	0.0323 (3)
O2	0.92268 (15)	0.10661 (9)	1.11372 (9)	0.0319 (3)
O3	0.78116 (16)	−0.04005 (9)	0.88575 (11)	0.0414 (4)
P1	0.93236 (4)	0.27707 (3)	0.93926 (3)	0.01703 (9)
P2	0.69669 (4)	0.20131 (3)	0.93074 (3)	0.01628 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02552 (10)	0.04377 (12)	0.01665 (9)	0.00896 (8)	0.00157 (7)	−0.00067 (7)
C1	0.0176 (7)	0.0164 (8)	0.0182 (7)	0.0011 (6)	0.0023 (6)	0.0023 (6)
C2	0.0143 (7)	0.0169 (8)	0.0235 (8)	−0.0002 (6)	0.0026 (6)	0.0001 (6)
C3	0.0182 (8)	0.0207 (8)	0.0276 (9)	0.0019 (6)	0.0046 (7)	0.0043 (7)
C4	0.0206 (8)	0.0178 (8)	0.0419 (11)	0.0024 (7)	0.0066 (8)	0.0052 (8)
C5	0.0199 (8)	0.0207 (9)	0.0411 (11)	−0.0001 (7)	0.0082 (7)	−0.0073 (8)
C6	0.0157 (8)	0.0255 (9)	0.0275 (9)	−0.0033 (7)	0.0043 (7)	−0.0059 (7)
C7	0.0319 (10)	0.0400 (12)	0.0285 (10)	0.0005 (9)	0.0054 (8)	−0.0085 (9)
C8	0.0249 (9)	0.0226 (9)	0.0231 (8)	−0.0032 (7)	−0.0010 (7)	−0.0033 (7)
C9	0.0294 (10)	0.0336 (11)	0.0336 (10)	0.0018 (8)	−0.0116 (8)	−0.0055 (8)
C10	0.0300 (10)	0.0246 (10)	0.0391 (11)	−0.0069 (8)	0.0027 (8)	−0.0087 (8)
C11	0.0276 (9)	0.0251 (9)	0.0308 (10)	−0.0024 (7)	0.0117 (8)	0.0032 (7)
C12	0.0234 (9)	0.0364 (11)	0.0422 (12)	0.0015 (8)	0.0143 (8)	0.0052 (9)
C13	0.0399 (12)	0.0344 (11)	0.0361 (11)	0.0085 (9)	0.0196 (9)	0.0133 (9)
C14	0.0299 (9)	0.0204 (9)	0.0223 (8)	−0.0018 (7)	0.0114 (7)	−0.0012 (7)
C15	0.0451 (12)	0.0228 (10)	0.0350 (10)	−0.0046 (8)	0.0183 (9)	0.0034 (8)
C16	0.0311 (10)	0.0292 (10)	0.0375 (11)	−0.0005 (8)	0.0180 (8)	−0.0041 (8)
C17	0.0178 (8)	0.0312 (10)	0.0248 (9)	0.0018 (7)	−0.0006 (7)	−0.0054 (7)
C18	0.0294 (11)	0.0354 (12)	0.0529 (14)	−0.0051 (9)	−0.0041 (9)	−0.0149 (10)
C19	0.0230 (9)	0.0397 (12)	0.0371 (11)	0.0074 (8)	−0.0049 (8)	−0.0009 (9)
C20	0.0287 (9)	0.0202 (8)	0.0196 (8)	0.0043 (7)	−0.0013 (7)	−0.0001 (7)
C21	0.0258 (9)	0.0152 (8)	0.0276 (9)	0.0008 (7)	−0.0011 (7)	−0.0008 (7)
C22	0.0278 (9)	0.0239 (9)	0.0260 (9)	0.0063 (7)	−0.0052 (7)	−0.0019 (7)
Mn1	0.01885 (13)	0.01605 (13)	0.01478 (12)	0.00353 (9)	−0.00050 (9)	−0.00087 (9)
N1	0.0188 (7)	0.0206 (7)	0.0219 (7)	−0.0003 (6)	0.0029 (5)	−0.0002 (6)
O1	0.0248 (7)	0.0337 (8)	0.0383 (8)	0.0106 (6)	0.0031 (6)	0.0014 (6)
O2	0.0471 (9)	0.0270 (7)	0.0209 (7)	−0.0013 (6)	0.0008 (6)	0.0008 (5)
O3	0.0465 (9)	0.0214 (7)	0.0525 (10)	−0.0018 (6)	−0.0119 (7)	−0.0063 (7)
P1	0.01598 (19)	0.0173 (2)	0.0180 (2)	0.00095 (15)	0.00251 (15)	0.00128 (15)
P2	0.0167 (2)	0.0154 (2)	0.01706 (19)	0.00041 (15)	0.00292 (15)	−0.00067 (15)

Geometric parameters (Å, º)

Br1—Mn1	2.5231 (3)	C12—H12B	0.9800
C1—C2	1.508 (2)	C12—H12C	0.9800
C1—P1	1.8707 (17)	C13—H13A	0.9800
C1—P2	1.8715 (17)	C13—H13B	0.9800
C1—H1	1.0000	C13—H13C	0.9800
C2—N1	1.345 (2)	C14—C16	1.532 (3)
C2—C3	1.390 (2)	C14—C15	1.539 (3)
C3—C4	1.383 (3)	C14—P2	1.8500 (17)
C3—H3	0.9500	C14—H14	1.0000
C4—C5	1.380 (3)	C15—H15A	0.9800
C4—H4	0.9500	C15—H15B	0.9800
C5—C6	1.397 (3)	C15—H15C	0.9800
C5—H5	0.9500	C16—H16A	0.9800
C6—N1	1.340 (2)	C16—H16B	0.9800
C6—C7	1.500 (3)	C16—H16C	0.9800
C7—H7A	0.9800	C17—C18	1.528 (3)
C7—H7B	0.9800	C17—C19	1.528 (3)
C7—H7C	0.9800	C17—P2	1.8509 (18)
C8—C9	1.534 (3)	C17—H17	1.0000
C8—C10	1.535 (3)	C18—H18A	0.9800
C8—P1	1.8515 (18)	C18—H18B	0.9800
C8—H8	1.0000	C18—H18C	0.9800
C9—H9A	0.9800	C19—H19A	0.9800
C9—H9B	0.9800	C19—H19B	0.9800
C9—H9C	0.9800	C19—H19C	0.9800
C10—H10A	0.9800	C20—O1	1.142 (2)
C10—H10B	0.9800	C20—Mn1	1.8279 (19)
C10—H10C	0.9800	C21—O2	1.136 (2)
C11—C13	1.517 (3)	C21—Mn1	1.7842 (19)
C11—C12	1.534 (3)	C22—O3	1.142 (2)
C11—P1	1.8724 (19)	C22—Mn1	1.829 (2)
C11—H11	1.0000	Mn1—P1	2.3247 (5)
C12—H12A	0.9800	Mn1—P2	2.3351 (5)
C2—C1—P1	120.72 (12)	C15—C14—P2	111.27 (13)
C2—C1—P2	124.01 (12)	C16—C14—H14	106.4
P1—C1—P2	95.63 (8)	C15—C14—H14	106.4
C2—C1—H1	104.8	P2—C14—H14	106.4
P1—C1—H1	104.8	C14—C15—H15A	109.5
P2—C1—H1	104.8	C14—C15—H15B	109.5
N1—C2—C3	122.55 (16)	H15A—C15—H15B	109.5
N1—C2—C1	116.79 (15)	C14—C15—H15C	109.5
C3—C2—C1	120.62 (15)	H15A—C15—H15C	109.5
C4—C3—C2	118.82 (17)	H15B—C15—H15C	109.5
C4—C3—H3	120.6	C14—C16—H16A	109.5
C2—C3—H3	120.6	C14—C16—H16B	109.5
C5—C4—C3	118.89 (17)	H16A—C16—H16B	109.5
C5—C4—H4	120.6	C14—C16—H16C	109.5
C3—C4—H4	120.6	H16A—C16—H16C	109.5
C4—C5—C6	119.28 (17)	H16B—C16—H16C	109.5
C4—C5—H5	120.4	C18—C17—C19	111.81 (16)
C6—C5—H5	120.4	C18—C17—P2	111.74 (14)
N1—C6—C5	121.94 (17)	C19—C17—P2	116.80 (14)
N1—C6—C7	116.91 (17)	C18—C17—H17	105.1
C5—C6—C7	121.15 (17)	C19—C17—H17	105.1
C6—C7—H7A	109.5	P2—C17—H17	105.1
C6—C7—H7B	109.5	C17—C18—H18A	109.5
H7A—C7—H7B	109.5	C17—C18—H18B	109.5
C6—C7—H7C	109.5	H18A—C18—H18B	109.5
H7A—C7—H7C	109.5	C17—C18—H18C	109.5
H7B—C7—H7C	109.5	H18A—C18—H18C	109.5
C9—C8—C10	108.92 (16)	H18B—C18—H18C	109.5
C9—C8—P1	108.84 (13)	C17—C19—H19A	109.5
C10—C8—P1	116.94 (14)	C17—C19—H19B	109.5
C9—C8—H8	107.2	H19A—C19—H19B	109.5
C10—C8—H8	107.2	C17—C19—H19C	109.5
P1—C8—H8	107.2	H19A—C19—H19C	109.5
C8—C9—H9A	109.5	H19B—C19—H19C	109.5
C8—C9—H9B	109.5	O1—C20—Mn1	178.35 (17)
H9A—C9—H9B	109.5	O2—C21—Mn1	179.51 (19)
C8—C9—H9C	109.5	O3—C22—Mn1	178.81 (18)
H9A—C9—H9C	109.5	C21—Mn1—C20	91.33 (8)
H9B—C9—H9C	109.5	C21—Mn1—C22	92.94 (8)
C8—C10—H10A	109.5	C20—Mn1—C22	95.24 (8)
C8—C10—H10B	109.5	C21—Mn1—P1	91.38 (6)
H10A—C10—H10B	109.5	C20—Mn1—P1	95.30 (6)
C8—C10—H10C	109.5	C22—Mn1—P1	168.51 (6)
H10A—C10—H10C	109.5	C21—Mn1—P2	91.32 (6)
H10B—C10—H10C	109.5	C20—Mn1—P2	168.09 (6)
C13—C11—C12	110.95 (17)	C22—Mn1—P2	96.21 (6)
C13—C11—P1	114.91 (14)	P1—Mn1—P2	73.032 (17)
C12—C11—P1	111.11 (13)	C21—Mn1—Br1	178.86 (6)
C13—C11—H11	106.4	C20—Mn1—Br1	87.86 (6)
C12—C11—H11	106.4	C22—Mn1—Br1	86.34 (6)
P1—C11—H11	106.4	P1—Mn1—Br1	89.492 (14)
C11—C12—H12A	109.5	P2—Mn1—Br1	89.641 (14)
C11—C12—H12B	109.5	C6—N1—C2	118.43 (15)
H12A—C12—H12B	109.5	C8—P1—C1	110.24 (8)
C11—C12—H12C	109.5	C8—P1—C11	102.93 (9)
H12A—C12—H12C	109.5	C1—P1—C11	107.98 (8)
H12B—C12—H12C	109.5	C8—P1—Mn1	114.31 (6)
C11—C13—H13A	109.5	C1—P1—Mn1	94.49 (5)
C11—C13—H13B	109.5	C11—P1—Mn1	126.09 (7)
H13A—C13—H13B	109.5	C14—P2—C17	109.84 (9)
C11—C13—H13C	109.5	C14—P2—C1	110.00 (8)
H13A—C13—H13C	109.5	C17—P2—C1	104.75 (8)
H13B—C13—H13C	109.5	C14—P2—Mn1	117.21 (6)
C16—C14—C15	109.99 (16)	C17—P2—Mn1	118.65 (6)
C16—C14—P2	115.87 (13)	C1—P2—Mn1	94.13 (5)
P1—C1—C2—N1	−67.21 (18)	P2—C1—P1—Mn1	13.67 (6)
P2—C1—C2—N1	55.4 (2)	C13—C11—P1—C8	−133.76 (16)
P1—C1—C2—C3	110.34 (16)	C12—C11—P1—C8	99.24 (16)
P2—C1—C2—C3	−127.07 (15)	C13—C11—P1—C1	−17.17 (17)
N1—C2—C3—C4	2.8 (3)	C12—C11—P1—C1	−144.17 (15)
C1—C2—C3—C4	−174.63 (15)	C13—C11—P1—Mn1	92.61 (15)
C2—C3—C4—C5	−1.2 (3)	C12—C11—P1—Mn1	−34.39 (18)
C3—C4—C5—C6	−1.6 (3)	C16—C14—P2—C17	−43.55 (17)
C4—C5—C6—N1	3.1 (3)	C15—C14—P2—C17	83.07 (16)
C4—C5—C6—C7	−176.34 (17)	C16—C14—P2—C1	71.24 (16)
C5—C6—N1—C2	−1.6 (3)	C15—C14—P2—C1	−162.14 (14)
C7—C6—N1—C2	177.88 (16)	C16—C14—P2—Mn1	177.11 (12)
C3—C2—N1—C6	−1.4 (2)	C15—C14—P2—Mn1	−56.27 (16)
C1—C2—N1—C6	176.10 (15)	C18—C17—P2—C14	−57.39 (16)
C9—C8—P1—C1	168.34 (13)	C19—C17—P2—C14	73.12 (17)
C10—C8—P1—C1	−67.77 (16)	C18—C17—P2—C1	−175.49 (14)
C9—C8—P1—C11	−76.69 (15)	C19—C17—P2—C1	−44.98 (17)
C10—C8—P1—C11	47.20 (16)	C18—C17—P2—Mn1	81.29 (15)
C9—C8—P1—Mn1	63.38 (14)	C19—C17—P2—Mn1	−148.20 (13)
C10—C8—P1—Mn1	−172.72 (12)	C2—C1—P2—C14	−25.96 (16)
C2—C1—P1—C8	31.12 (16)	P1—C1—P2—C14	107.34 (9)
P2—C1—P1—C8	−104.30 (9)	C2—C1—P2—C17	92.03 (15)
C2—C1—P1—C11	−80.61 (15)	P1—C1—P2—C17	−134.67 (8)
P2—C1—P1—C11	143.97 (8)	C2—C1—P2—Mn1	−146.90 (13)
C2—C1—P1—Mn1	149.09 (12)	P1—C1—P2—Mn1	−13.60 (6)