Transition-metal complexes of group 12 with 1,1′-bis­(phosphan­yl)ferrocene ligands

Chaudhary, K.; Trivedi, M.; Masram, D.T.; Rath, N.P.

doi:10.1107/S2053229621004162

Transition-metal complexes of group 12 with 1,1′-bis(phosphanyl)ferrocene ligands

K. Chaudhary, M. Trivedi, D. T. Masram and N. P. Rath

The syntheses of four new cadmium and zinc complexes with 1,1′-bis(phosphanyl)ferrocene ligands and their phosphine chalcogenide derivatives are reported. The complexes were characterized by elemental analyses and IR, ¹H NMR, ³¹P NMR and electronic absorption spectroscopy. The crystal structures of dichlorido[1-diphenylphosphinoyl-1′-(di-tert-butylphosphanyl)ferrocene-κ²O,P]cadmium(II), [CdCl₂{(C₁₇H₁₄OP)(C₁₃H₂₂P)Fe}] or CdCl₂(κ²P,O-dppOdtbpf) (1), bis[μ-(tert-butyl)(1′-diphenylphosphinoylferrocen-1-yl)phosphinato-κ³O,O′:O′′]bis[chloridozinc(II)], [Zn₂{(C₉H₁₃O₂P)(C₁₇H₁₄OP)Fe}₂Cl₂] or [ZnOCl{κ²O,O′-Ph₂POFcPO₂(t-Bu)}]₂ (2), 1,1′-bis(di-tert-butylthiophosphinoyl)ferrocene, [Fe(C₁₃H₂₂PS)₂] or dtbpfS₂ (3), and [1,1′-bis(dicyclohexylphosphanyl)ferrocene-κ²P,P′][chlorido/cyanido(0.25/1.75)]zinc(II), [Zn(CN)_1.75Cl_0.25{(C₁₇H₂₆P)₂Fe}] or Zn(CN)₂(κ²-dcpf) (4), were determined crystallographically. Compound 1 has tetrahedral geometry in which the Cd^II centre is coordinated by one dppOdtbpf ligand in a κ²-manner and by two Cl atoms, while compound 2 displays a centrosymmetric dimeric unit in which two oxide atoms bridge the two Zn atoms to generate an eight-membered ring. Compound 3 revealed a sandwich structure with both phosphane groups sulfurized. In compound 4, the Zn^II atom adopts a tetrahedral geometry by coordinating to the 1,1′-bis(dicyclohexylphosphanyl)ferrocene ligand in a κ²-manner and to two cyanide ligands.

Keywords: 1,1′-bis(phosphanyl)ferrocene; monooxidation; cadmium; zinc; electrochemistry; crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229621004162/yd3016sup1.cif Contains datablocks Complex-1, Complex-2, Complex-3, Complex-4, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229621004162/yd3016Complex-1sup2.hkl Contains datablock Complex-1
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229621004162/yd3016Complex-2sup3.hkl Contains datablock Complex-2
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229621004162/yd3016Complex-3sup4.hkl Contains datablock Complex-3
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229621004162/yd3016Complex-4sup5.hkl Contains datablock Complex-4
	Portable Document Format (PDF) file https://doi.org/10.1107/S2053229621004162/yd3016sup6.pdf Additional tables and figures

CCDC references: 2078531; 1995191; 1846832; 1834034

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015) for Complex-1, Complex-2; APEX2 (Bruker, 2013) for Complex-3, Complex-4. Cell refinement: CrysAlis PRO (Rigaku OD, 2015) for Complex-1, Complex-2; SAINT (Bruker, 2013) for Complex-3, Complex-4. Data reduction: CrysAlis PRO (Rigaku OD, 2015) for Complex-1, Complex-2; SAINT (Bruker, 2013) for Complex-3, Complex-4. Program(s) used to solve structure: SHELXTL (Bruker, 2013) for Complex-1, Complex-2; SHELXT2014 (Sheldrick, 2015a) for Complex-3, Complex-4. For all structures, program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: SHELXTL (Bruker, 2013); software used to prepare material for publication: SHELXTL (Bruker, 2013).

Dichlorido[1-diphenylphosphinoyl-1'-(di-tert-butylphosphanyl)ferrocene-\ κ²O,P]cadmium(II) (Complex-1) top

Crystal data top

[CdCl₂{(C₁₇H₁₄OP)(C₁₃H₂₂P)Fe}]	Z = 2
M_r = 713.68	F(000) = 724
Triclinic, P1	D_x = 1.578 Mg m⁻³
a = 9.8113 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8273 (4) Å	Cell parameters from 7873 reflections
c = 16.6898 (5) Å	θ = 3.7–27.6°
α = 91.454 (3)°	µ = 1.50 mm⁻¹
β = 106.989 (3)°	T = 293 K
γ = 101.534 (3)°	Needle, yellow
V = 1501.86 (10) Å³	0.40 × 0.30 × 0.15 mm

Data collection top

Rigaku Xcalibur Sapphire3 diffractometer	7295 independent reflections
Radiation source: fine-focus sealed X-ray tube	5458 reflections with I > 2σ(I)
Detector resolution: 15.9853 pixels mm^-1	R_int = 0.039
ω scans	θ_max = 29.5°, θ_min = 3.3°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −13→13
T_min = 0.907, T_max = 1.000	k = −13→13
22618 measured reflections	l = −21→22

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.025P)² + 2.1154P] where P = (F_o² + 2F_c²)/3
7295 reflections	(Δ/σ)_max = 0.001
331 parameters	Δρ_max = 0.64 e Å⁻³
106 restraints	Δρ_min = −0.97 e Å⁻³

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.

Refinement. Intensity data sets for 1 and 2 were collected on a X-calibur-S Oxford CCD area detector diffractometer using graphite monochromated Mo-K? radiation at 293 (2) K. Intensity data sets for 3 and 4 were collected on a Bruker APEX II CCD area detector diffractometer using graphite monochromated Mo-K? radiation at 100 (2) and 100 (2) K. CrysAlisPro RED and Apex2, software packages were used for data collection and data integration for 1, 2 (Rigaku Oxford Diffraction, 2015)and 3, 4 ?(Bruker, 2009)?. The structures were solved by direct methods using SHELXS-97, and refined by full matrix least-squares with SHELXL-2014 ?(Sheldrick, 2015)?. The non-hydrogen atoms were refined with anisotropic thermal parameters.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cd1	0.93178 (18)	0.3474 (2)	0.25564 (15)	0.0294 (5)	0.469 (11)
Cl1	1.080 (3)	0.362 (2)	0.4009 (9)	0.054 (2)	0.469 (11)
O1	0.7290 (6)	0.2019 (7)	0.2517 (5)	0.0392 (2)	0.469 (11)
Cd1'	0.9140 (4)	0.3387 (3)	0.25989 (17)	0.0644 (6)	0.531 (11)
Cl1'	1.068 (2)	0.3321 (19)	0.4024 (8)	0.054 (2)	0.531 (11)
O1'	0.7433 (5)	0.1741 (7)	0.2665 (4)	0.0392 (2)	0.531 (11)
Cl2	1.0320 (3)	0.2498 (4)	0.15838 (13)	0.0651 (6)	0.830 (9)
Cl2'	0.9809 (19)	0.2004 (14)	0.1668 (5)	0.0644 (6)	0.170 (9)
Fe1	0.54139 (5)	0.47368 (5)	0.28862 (3)	0.03023 (13)
P1	0.60267 (11)	0.14704 (11)	0.28304 (6)	0.0392 (2)
P2	0.84379 (10)	0.57215 (10)	0.21443 (6)	0.0335 (2)
C1	0.5571 (4)	0.2868 (4)	0.3326 (2)	0.0325 (8)
C2	0.4221 (4)	0.3203 (4)	0.3345 (2)	0.0362 (8)
H2	0.328876	0.269047	0.306080	0.043*
C3	0.4564 (4)	0.4456 (4)	0.3873 (2)	0.0416 (9)
H3	0.389296	0.491141	0.399375	0.050*
C4	0.6094 (4)	0.4891 (4)	0.4184 (2)	0.0414 (9)
H4	0.660357	0.568628	0.454224	0.050*
C5	0.6721 (4)	0.3928 (4)	0.3864 (2)	0.0377 (9)
H5	0.771573	0.396939	0.398001	0.045*
C6	0.6577 (4)	0.5650 (4)	0.2127 (2)	0.0316 (8)
C7	0.5390 (4)	0.4531 (4)	0.1673 (2)	0.0405 (9)
H7	0.547610	0.373318	0.139680	0.049*
C8	0.4067 (4)	0.4851 (5)	0.1720 (3)	0.0516 (12)
H8	0.313671	0.430122	0.147775	0.062*
C9	0.4404 (5)	0.6140 (5)	0.2193 (3)	0.0537 (12)
H9	0.373363	0.659043	0.231858	0.064*
C10	0.5933 (4)	0.6637 (4)	0.2448 (3)	0.0417 (9)
H10	0.643722	0.746962	0.277135	0.050*
C11	0.4603 (8)	0.0644 (7)	0.1910 (3)	0.050 (5)	0.63 (3)
C12	0.3180 (9)	0.0829 (9)	0.1613 (7)	0.0686 (18)	0.63 (3)
H12	0.286080	0.144997	0.190829	0.082*	0.63 (3)
C13	0.2232 (9)	0.0086 (8)	0.0873 (7)	0.0686 (18)	0.63 (3)
H13	0.127965	0.021051	0.067419	0.082*	0.63 (3)
C14	0.2709 (11)	−0.0842 (8)	0.0431 (3)	0.0686 (18)	0.63 (3)
H14	0.207484	−0.133840	−0.006345	0.082*	0.63 (3)
C15	0.4132 (10)	−0.1027 (11)	0.0729 (7)	0.0686 (18)	0.63 (3)
H15	0.445119	−0.164784	0.043300	0.082*	0.63 (3)
C16	0.5080 (6)	−0.0284 (10)	0.1468 (7)	0.0686 (18)	0.63 (3)
H16	0.603237	−0.040839	0.166710	0.082*	0.63 (3)
C11'	0.4586 (10)	0.0576 (12)	0.1908 (5)	0.037 (6)	0.37 (3)
C12'	0.3136 (12)	0.0596 (16)	0.1816 (9)	0.058 (3)	0.37 (3)
H12'	0.289109	0.102005	0.224311	0.069*	0.37 (3)
C13'	0.2052 (10)	−0.0016 (13)	0.1084 (10)	0.058 (3)	0.37 (3)
H13'	0.108127	−0.000276	0.102239	0.069*	0.37 (3)
C14'	0.2418 (15)	−0.0650 (14)	0.0446 (5)	0.058 (3)	0.37 (3)
H14'	0.169210	−0.105957	−0.004377	0.069*	0.37 (3)
C15'	0.3868 (16)	−0.067 (2)	0.0538 (8)	0.058 (3)	0.37 (3)
H15'	0.411275	−0.109359	0.011077	0.069*	0.37 (3)
C16'	0.4952 (10)	−0.0057 (16)	0.1270 (10)	0.058 (3)	0.37 (3)
H16'	0.592260	−0.007079	0.133148	0.069*	0.37 (3)
C17	0.6251 (4)	0.0248 (4)	0.3618 (2)	0.0371 (9)
C18	0.5066 (5)	−0.0626 (4)	0.3754 (3)	0.0530 (11)
H18	0.413058	−0.065510	0.339924	0.064*
C19	0.5265 (5)	−0.1460 (5)	0.4418 (3)	0.0607 (13)
H19	0.446629	−0.204408	0.451135	0.073*
C20	0.6640 (5)	−0.1418 (4)	0.4933 (3)	0.0537 (12)
H20	0.677640	−0.197652	0.537902	0.064*
C21	0.7817 (5)	−0.0565 (5)	0.4799 (3)	0.0533 (11)
H21	0.875051	−0.055161	0.515200	0.064*
C22	0.7636 (4)	0.0276 (4)	0.4146 (3)	0.0476 (10)
H22	0.844298	0.086085	0.406128	0.057*
C23	0.9668 (4)	0.7198 (4)	0.2922 (3)	0.0457 (10)
C24	0.9479 (6)	0.8653 (5)	0.2673 (3)	0.0660 (14)
H24A	0.965752	0.879002	0.214174	0.099*
H24B	0.850152	0.873816	0.262620	0.099*
H24C	1.015954	0.934438	0.309422	0.099*
C25	1.1269 (5)	0.7094 (6)	0.3044 (3)	0.0728 (15)
H25A	1.139110	0.618271	0.320078	0.109*
H25B	1.149697	0.725144	0.252837	0.109*
H25C	1.191023	0.778440	0.347996	0.109*
C26	0.9389 (5)	0.6949 (5)	0.3771 (3)	0.0527 (11)
H26A	0.951221	0.603340	0.391748	0.079*
H26B	1.006896	0.763279	0.419770	0.079*
H26C	0.841095	0.702656	0.372968	0.079*
C27	0.8360 (5)	0.6023 (5)	0.1020 (3)	0.0506 (11)
C28	0.7577 (5)	0.4663 (5)	0.0487 (3)	0.0619 (13)
H28A	0.808779	0.394351	0.069098	0.093*
H28B	0.659869	0.441053	0.051968	0.093*
H28C	0.754829	0.477420	−0.008703	0.093*
C29	0.7532 (7)	0.7157 (6)	0.0687 (3)	0.0773 (17)
H29A	0.801935	0.802343	0.102042	0.116*
H29B	0.750380	0.726072	0.011228	0.116*
H29C	0.655420	0.689705	0.071899	0.116*
C30	0.9925 (6)	0.6397 (6)	0.0950 (3)	0.0820 (17)
H30A	1.044325	0.725699	0.128390	0.123*
H30B	1.042359	0.566747	0.115083	0.123*
H30C	0.988091	0.649830	0.037339	0.123*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0142 (8)	0.0401 (7)	0.0351 (7)	0.0018 (5)	0.0117 (4)	0.0076 (5)
Cl1	0.043 (3)	0.062 (7)	0.0459 (7)	0.007 (4)	−0.0034 (11)	0.017 (2)
O1	0.0429 (6)	0.0408 (6)	0.0379 (6)	0.0165 (5)	0.0126 (4)	0.0096 (4)
Cd1'	0.0886 (14)	0.0610 (11)	0.0401 (8)	0.0459 (10)	−0.0047 (8)	−0.0034 (7)
Cl1'	0.043 (3)	0.062 (7)	0.0459 (7)	0.007 (4)	−0.0034 (11)	0.017 (2)
O1'	0.0429 (6)	0.0408 (6)	0.0379 (6)	0.0165 (5)	0.0126 (4)	0.0096 (4)
Cl2	0.0505 (10)	0.0838 (15)	0.0654 (10)	0.0228 (11)	0.0204 (9)	−0.0121 (9)
Cl2'	0.0886 (14)	0.0610 (11)	0.0401 (8)	0.0459 (10)	−0.0047 (8)	−0.0034 (7)
Fe1	0.0288 (3)	0.0337 (3)	0.0286 (3)	0.0073 (2)	0.0085 (2)	0.0064 (2)
P1	0.0429 (6)	0.0408 (6)	0.0379 (6)	0.0165 (5)	0.0126 (4)	0.0096 (4)
P2	0.0343 (5)	0.0375 (5)	0.0316 (5)	0.0100 (4)	0.0130 (4)	0.0047 (4)
C1	0.0336 (19)	0.033 (2)	0.0310 (19)	0.0070 (16)	0.0106 (15)	0.0090 (16)
C2	0.035 (2)	0.038 (2)	0.038 (2)	0.0050 (17)	0.0161 (16)	0.0069 (17)
C3	0.050 (2)	0.045 (2)	0.038 (2)	0.0134 (19)	0.0242 (19)	0.0081 (18)
C4	0.049 (2)	0.040 (2)	0.030 (2)	0.0027 (19)	0.0089 (18)	−0.0019 (17)
C5	0.036 (2)	0.044 (2)	0.0293 (19)	0.0059 (17)	0.0057 (16)	0.0118 (17)
C6	0.0326 (19)	0.034 (2)	0.0306 (19)	0.0092 (16)	0.0114 (15)	0.0109 (16)
C7	0.045 (2)	0.048 (2)	0.0220 (18)	−0.0001 (19)	0.0065 (16)	0.0043 (17)
C8	0.032 (2)	0.076 (3)	0.040 (2)	0.010 (2)	0.0017 (18)	0.028 (2)
C9	0.045 (3)	0.067 (3)	0.066 (3)	0.033 (2)	0.027 (2)	0.037 (3)
C10	0.044 (2)	0.038 (2)	0.051 (2)	0.0147 (18)	0.0217 (19)	0.0171 (19)
C11	0.074 (7)	0.044 (11)	0.039 (8)	0.022 (7)	0.019 (6)	0.010 (7)
C12	0.088 (4)	0.070 (3)	0.044 (3)	0.031 (3)	0.004 (2)	−0.009 (2)
C13	0.088 (4)	0.070 (3)	0.044 (3)	0.031 (3)	0.004 (2)	−0.009 (2)
C14	0.088 (4)	0.070 (3)	0.044 (3)	0.031 (3)	0.004 (2)	−0.009 (2)
C15	0.088 (4)	0.070 (3)	0.044 (3)	0.031 (3)	0.004 (2)	−0.009 (2)
C16	0.088 (4)	0.070 (3)	0.044 (3)	0.031 (3)	0.004 (2)	−0.009 (2)
C11'	0.046 (8)	0.026 (14)	0.031 (10)	0.011 (9)	−0.004 (7)	0.005 (10)
C12'	0.057 (5)	0.066 (5)	0.041 (4)	0.023 (4)	−0.004 (3)	−0.012 (4)
C13'	0.057 (5)	0.066 (5)	0.041 (4)	0.023 (4)	−0.004 (3)	−0.012 (4)
C14'	0.057 (5)	0.066 (5)	0.041 (4)	0.023 (4)	−0.004 (3)	−0.012 (4)
C15'	0.057 (5)	0.066 (5)	0.041 (4)	0.023 (4)	−0.004 (3)	−0.012 (4)
C16'	0.057 (5)	0.066 (5)	0.041 (4)	0.023 (4)	−0.004 (3)	−0.012 (4)
C17	0.046 (2)	0.032 (2)	0.036 (2)	0.0158 (17)	0.0099 (17)	0.0066 (16)
C18	0.040 (2)	0.048 (3)	0.064 (3)	0.007 (2)	0.006 (2)	0.016 (2)
C19	0.059 (3)	0.047 (3)	0.079 (4)	0.008 (2)	0.026 (3)	0.024 (3)
C20	0.077 (3)	0.042 (3)	0.047 (3)	0.025 (2)	0.018 (2)	0.015 (2)
C21	0.047 (3)	0.059 (3)	0.050 (3)	0.019 (2)	0.004 (2)	0.017 (2)
C22	0.040 (2)	0.050 (3)	0.052 (3)	0.011 (2)	0.0102 (19)	0.016 (2)
C23	0.039 (2)	0.044 (2)	0.051 (3)	−0.0015 (18)	0.0152 (19)	−0.001 (2)
C24	0.077 (3)	0.042 (3)	0.077 (4)	−0.006 (2)	0.032 (3)	0.001 (2)
C25	0.040 (3)	0.084 (4)	0.084 (4)	−0.007 (3)	0.016 (3)	−0.004 (3)
C26	0.054 (3)	0.053 (3)	0.042 (2)	−0.004 (2)	0.011 (2)	−0.011 (2)
C27	0.065 (3)	0.062 (3)	0.037 (2)	0.024 (2)	0.025 (2)	0.015 (2)
C28	0.077 (3)	0.083 (4)	0.030 (2)	0.026 (3)	0.017 (2)	0.003 (2)
C29	0.117 (5)	0.081 (4)	0.051 (3)	0.045 (4)	0.034 (3)	0.031 (3)
C30	0.085 (4)	0.109 (5)	0.070 (4)	0.011 (3)	0.055 (3)	0.016 (3)

Geometric parameters (Å, º) top

Cd1—O1	2.187 (5)	C14—C15	1.3900
Cd1—Cl2	2.398 (3)	C14—H14	0.9300
Cd1—Cl1	2.417 (8)	C15—C16	1.3900
Cd1—P2	2.567 (3)	C15—H15	0.9300
O1—P1	1.493 (5)	C16—H16	0.9300
Cd1'—O1'	2.114 (5)	C11'—C12'	1.3900
Cd1'—Cl2'	2.352 (8)	C11'—C16'	1.3900
Cd1'—Cl1'	2.427 (7)	C12'—C13'	1.3900
Cd1'—P2	2.594 (3)	C12'—H12'	0.9300
O1'—P1	1.459 (4)	C13'—C14'	1.3900
Fe1—C1	2.012 (3)	C13'—H13'	0.9300
Fe1—C7	2.022 (4)	C14'—C15'	1.3900
Fe1—C2	2.026 (4)	C14'—H14'	0.9300
Fe1—C8	2.029 (4)	C15'—C16'	1.3900
Fe1—C9	2.044 (4)	C15'—H15'	0.9300
Fe1—C10	2.046 (4)	C16'—H16'	0.9300
Fe1—C5	2.046 (4)	C17—C18	1.380 (5)
Fe1—C6	2.050 (3)	C17—C22	1.382 (5)
Fe1—C3	2.054 (4)	C18—C19	1.386 (6)
Fe1—C4	2.063 (4)	C18—H18	0.9300
P1—C1	1.782 (4)	C19—C20	1.363 (6)
P1—C11	1.789 (4)	C19—H19	0.9300
P1—C17	1.799 (4)	C20—C21	1.364 (6)
P1—C11'	1.817 (5)	C20—H20	0.9300
P2—C6	1.805 (4)	C21—C22	1.376 (5)
P2—C23	1.880 (4)	C21—H21	0.9300
P2—C27	1.889 (4)	C22—H22	0.9300
C1—C5	1.433 (5)	C23—C24	1.532 (6)
C1—C2	1.435 (5)	C23—C26	1.537 (6)
C2—C3	1.419 (5)	C23—C25	1.547 (6)
C2—H2	0.9300	C24—H24A	0.9600
C3—C4	1.408 (5)	C24—H24B	0.9600
C3—H3	0.9300	C24—H24C	0.9600
C4—C5	1.399 (5)	C25—H25A	0.9600
C4—H4	0.9300	C25—H25B	0.9600
C5—H5	0.9300	C25—H25C	0.9600
C6—C10	1.430 (5)	C26—H26A	0.9600
C6—C7	1.438 (5)	C26—H26B	0.9600
C7—C8	1.418 (6)	C26—H26C	0.9600
C7—H7	0.9300	C27—C28	1.516 (6)
C8—C9	1.403 (6)	C27—C29	1.529 (6)
C8—H8	0.9300	C27—C30	1.545 (6)
C9—C10	1.411 (6)	C28—H28A	0.9600
C9—H9	0.9300	C28—H28B	0.9600
C10—H10	0.9300	C28—H28C	0.9600
C11—C12	1.3900	C29—H29A	0.9600
C11—C16	1.3900	C29—H29B	0.9600
C12—C13	1.3900	C29—H29C	0.9600
C12—H12	0.9300	C30—H30A	0.9600
C13—C14	1.3900	C30—H30B	0.9600
C13—H13	0.9300	C30—H30C	0.9600

O1—Cd1—Cl2	107.4 (2)	C9—C8—C7	108.2 (4)
O1—Cd1—Cl1	103.8 (6)	C9—C8—Fe1	70.4 (2)
Cl2—Cd1—Cl1	113.8 (9)	C7—C8—Fe1	69.3 (2)
O1—Cd1—P2	102.3 (2)	C9—C8—H8	125.9
Cl2—Cd1—P2	114.84 (12)	C7—C8—H8	125.9
Cl1—Cd1—P2	113.2 (6)	Fe1—C8—H8	126.0
P1—O1—Cd1	153.9 (5)	C8—C9—C10	108.5 (4)
O1'—Cd1'—Cl2'	91.8 (5)	C8—C9—Fe1	69.3 (2)
O1'—Cd1'—Cl1'	95.4 (5)	C10—C9—Fe1	69.9 (2)
Cl2'—Cd1'—Cl1'	109.3 (8)	C8—C9—H9	125.8
O1'—Cd1'—P2	116.9 (3)	C10—C9—H9	125.8
Cl2'—Cd1'—P2	119.3 (3)	Fe1—C9—H9	126.6
Cl1'—Cd1'—P2	118.7 (5)	C9—C10—C6	108.7 (4)
P1—O1'—Cd1'	141.9 (4)	C9—C10—Fe1	69.7 (2)
C1—Fe1—C7	105.90 (16)	C6—C10—Fe1	69.7 (2)
C1—Fe1—C2	41.64 (14)	C9—C10—H10	125.6
C7—Fe1—C2	119.72 (16)	C6—C10—H10	125.6
C1—Fe1—C8	120.12 (18)	Fe1—C10—H10	126.5
C7—Fe1—C8	40.98 (16)	C12—C11—C16	120.0
C2—Fe1—C8	103.09 (16)	C12—C11—P1	128.8 (5)
C1—Fe1—C9	155.89 (17)	C16—C11—P1	111.2 (5)
C7—Fe1—C9	68.40 (18)	C13—C12—C11	120.0
C2—Fe1—C9	119.27 (16)	C13—C12—H12	120.0
C8—Fe1—C9	40.29 (18)	C11—C12—H12	120.0
C1—Fe1—C10	161.42 (15)	C12—C13—C14	120.0
C7—Fe1—C10	68.64 (17)	C12—C13—H13	120.0
C2—Fe1—C10	156.70 (15)	C14—C13—H13	120.0
C8—Fe1—C10	68.17 (18)	C15—C14—C13	120.0
C9—Fe1—C10	40.37 (16)	C15—C14—H14	120.0
C1—Fe1—C5	41.35 (14)	C13—C14—H14	120.0
C7—Fe1—C5	125.20 (17)	C14—C15—C16	120.0
C2—Fe1—C5	68.87 (15)	C14—C15—H15	120.0
C8—Fe1—C5	159.27 (19)	C16—C15—H15	120.0
C9—Fe1—C5	160.31 (19)	C15—C16—C11	120.0
C10—Fe1—C5	126.36 (16)	C15—C16—H16	120.0
C1—Fe1—C6	123.45 (14)	C11—C16—H16	120.0
C7—Fe1—C6	41.36 (14)	C12'—C11'—C16'	120.0
C2—Fe1—C6	158.22 (15)	C12'—C11'—P1	120.5 (7)
C8—Fe1—C6	69.17 (15)	C16'—C11'—P1	119.4 (7)
C9—Fe1—C6	68.67 (15)	C11'—C12'—C13'	120.0
C10—Fe1—C6	40.86 (14)	C11'—C12'—H12'	120.0
C5—Fe1—C6	110.90 (14)	C13'—C12'—H12'	120.0
C1—Fe1—C3	69.06 (15)	C14'—C13'—C12'	120.0
C7—Fe1—C3	155.58 (16)	C14'—C13'—H13'	120.0
C2—Fe1—C3	40.69 (15)	C12'—C13'—H13'	120.0
C8—Fe1—C3	119.42 (17)	C13'—C14'—C15'	120.0
C9—Fe1—C3	105.96 (17)	C13'—C14'—H14'	120.0
C10—Fe1—C3	123.36 (16)	C15'—C14'—H14'	120.0
C5—Fe1—C3	67.62 (16)	C14'—C15'—C16'	120.0
C6—Fe1—C3	160.81 (16)	C14'—C15'—H15'	120.0
C1—Fe1—C4	68.63 (15)	C16'—C15'—H15'	120.0
C7—Fe1—C4	162.27 (16)	C15'—C16'—C11'	120.0
C2—Fe1—C4	68.15 (15)	C15'—C16'—H16'	120.0
C8—Fe1—C4	156.52 (18)	C11'—C16'—H16'	120.0
C9—Fe1—C4	123.54 (19)	C18—C17—C22	119.4 (4)
C10—Fe1—C4	110.89 (16)	C18—C17—P1	121.6 (3)
C5—Fe1—C4	39.80 (15)	C22—C17—P1	118.8 (3)
C6—Fe1—C4	126.57 (15)	C17—C18—C19	120.2 (4)
C3—Fe1—C4	40.00 (15)	C17—C18—H18	119.9
O1'—P1—C1	117.5 (3)	C19—C18—H18	119.9
O1—P1—C1	109.8 (3)	C20—C19—C18	119.6 (4)
O1—P1—C11	104.3 (4)	C20—C19—H19	120.2
C1—P1—C11	113.0 (3)	C18—C19—H19	120.2
O1'—P1—C17	103.0 (3)	C19—C20—C21	120.5 (4)
O1—P1—C17	118.1 (3)	C19—C20—H20	119.7
C1—P1—C17	103.18 (17)	C21—C20—H20	119.7
C11—P1—C17	108.8 (3)	C20—C21—C22	120.6 (4)
O1'—P1—C11'	110.5 (5)	C20—C21—H21	119.7
C1—P1—C11'	114.2 (4)	C22—C21—H21	119.7
C17—P1—C11'	107.0 (4)	C21—C22—C17	119.7 (4)
C6—P2—C23	108.75 (18)	C21—C22—H22	120.1
C6—P2—C27	102.28 (18)	C17—C22—H22	120.1
C23—P2—C27	113.2 (2)	C24—C23—C26	110.6 (4)
C6—P2—Cd1	113.68 (12)	C24—C23—C25	109.3 (4)
C23—P2—Cd1	108.22 (15)	C26—C23—C25	106.5 (4)
C27—P2—Cd1	110.75 (15)	C24—C23—P2	114.7 (3)
C6—P2—Cd1'	109.15 (15)	C26—C23—P2	107.2 (3)
C23—P2—Cd1'	109.63 (15)	C25—C23—P2	108.2 (3)
C27—P2—Cd1'	113.49 (16)	C23—C24—H24A	109.5
C5—C1—C2	106.8 (3)	C23—C24—H24B	109.5
C5—C1—P1	119.1 (3)	H24A—C24—H24B	109.5
C2—C1—P1	134.1 (3)	C23—C24—H24C	109.5
C5—C1—Fe1	70.6 (2)	H24A—C24—H24C	109.5
C2—C1—Fe1	69.7 (2)	H24B—C24—H24C	109.5
P1—C1—Fe1	126.21 (19)	C23—C25—H25A	109.5
C3—C2—C1	107.7 (3)	C23—C25—H25B	109.5
C3—C2—Fe1	70.7 (2)	H25A—C25—H25B	109.5
C1—C2—Fe1	68.7 (2)	C23—C25—H25C	109.5
C3—C2—H2	126.1	H25A—C25—H25C	109.5
C1—C2—H2	126.1	H25B—C25—H25C	109.5
Fe1—C2—H2	126.0	C23—C26—H26A	109.5
C4—C3—C2	108.3 (4)	C23—C26—H26B	109.5
C4—C3—Fe1	70.3 (2)	H26A—C26—H26B	109.5
C2—C3—Fe1	68.6 (2)	C23—C26—H26C	109.5
C4—C3—H3	125.9	H26A—C26—H26C	109.5
C2—C3—H3	125.9	H26B—C26—H26C	109.5
Fe1—C3—H3	126.8	C28—C27—C29	108.8 (4)
C5—C4—C3	108.8 (3)	C28—C27—C30	108.0 (4)
C5—C4—Fe1	69.5 (2)	C29—C27—C30	110.4 (4)
C3—C4—Fe1	69.7 (2)	C28—C27—P2	107.5 (3)
C5—C4—H4	125.6	C29—C27—P2	112.4 (3)
C3—C4—H4	125.6	C30—C27—P2	109.6 (3)
Fe1—C4—H4	126.8	C27—C28—H28A	109.5
C4—C5—C1	108.4 (3)	C27—C28—H28B	109.5
C4—C5—Fe1	70.7 (2)	H28A—C28—H28B	109.5
C1—C5—Fe1	68.05 (19)	C27—C28—H28C	109.5
C4—C5—H5	125.8	H28A—C28—H28C	109.5
C1—C5—H5	125.8	H28B—C28—H28C	109.5
Fe1—C5—H5	127.0	C27—C29—H29A	109.5
C10—C6—C7	106.2 (3)	C27—C29—H29B	109.5
C10—C6—P2	131.1 (3)	H29A—C29—H29B	109.5
C7—C6—P2	122.4 (3)	C27—C29—H29C	109.5
C10—C6—Fe1	69.4 (2)	H29A—C29—H29C	109.5
C7—C6—Fe1	68.3 (2)	H29B—C29—H29C	109.5
P2—C6—Fe1	131.13 (18)	C27—C30—H30A	109.5
C8—C7—C6	108.3 (4)	C27—C30—H30B	109.5
C8—C7—Fe1	69.8 (2)	H30A—C30—H30B	109.5
C6—C7—Fe1	70.4 (2)	C27—C30—H30C	109.5
C8—C7—H7	125.8	H30A—C30—H30C	109.5
C6—C7—H7	125.8	H30B—C30—H30C	109.5
Fe1—C7—H7	125.6

Cd1'—O1'—P1—C1	−15.6 (7)	O1—P1—C11—C12	−128.3 (7)
Cd1'—O1'—P1—C17	−128.1 (6)	C1—P1—C11—C12	−9.1 (7)
Cd1'—O1'—P1—C11'	117.9 (7)	C17—P1—C11—C12	104.8 (7)
Cd1—O1—P1—C1	30.6 (12)	O1—P1—C11—C16	51.3 (7)
Cd1—O1—P1—C11	151.9 (10)	C1—P1—C11—C16	170.5 (6)
Cd1—O1—P1—C17	−87.2 (11)	C17—P1—C11—C16	−75.6 (6)
O1'—P1—C1—C5	−27.4 (4)	C16—C11—C12—C13	0.0
O1—P1—C1—C5	−41.7 (4)	P1—C11—C12—C13	179.6 (6)
C11—P1—C1—C5	−157.7 (4)	C11—C12—C13—C14	0.0
C17—P1—C1—C5	85.1 (3)	C12—C13—C14—C15	0.0
C11'—P1—C1—C5	−159.2 (5)	C13—C14—C15—C16	0.0
O1'—P1—C1—C2	155.3 (4)	C14—C15—C16—C11	0.0
O1—P1—C1—C2	140.9 (4)	C12—C11—C16—C15	0.0
C11—P1—C1—C2	25.0 (5)	P1—C11—C16—C15	−179.6 (5)
C17—P1—C1—C2	−92.3 (4)	O1'—P1—C11'—C12'	−159.7 (9)
C11'—P1—C1—C2	23.4 (6)	C1—P1—C11'—C12'	−24.5 (9)
O1'—P1—C1—Fe1	59.0 (4)	C17—P1—C11'—C12'	88.9 (9)
O1—P1—C1—Fe1	44.6 (4)	O1'—P1—C11'—C16'	16.3 (12)
C11—P1—C1—Fe1	−71.3 (4)	C1—P1—C11'—C16'	151.5 (10)
C17—P1—C1—Fe1	171.4 (2)	C17—P1—C11'—C16'	−95.1 (11)
C11'—P1—C1—Fe1	−72.9 (5)	C16'—C11'—C12'—C13'	0.0
C5—C1—C2—C3	1.0 (4)	P1—C11'—C12'—C13'	176.0 (9)
P1—C1—C2—C3	178.6 (3)	C11'—C12'—C13'—C14'	0.0
Fe1—C1—C2—C3	−60.2 (3)	C12'—C13'—C14'—C15'	0.0
C5—C1—C2—Fe1	61.2 (2)	C13'—C14'—C15'—C16'	0.0
P1—C1—C2—Fe1	−121.2 (3)	C14'—C15'—C16'—C11'	0.0
C1—C2—C3—C4	−0.4 (4)	C12'—C11'—C16'—C15'	0.0
Fe1—C2—C3—C4	−59.3 (3)	P1—C11'—C16'—C15'	−176.0 (9)
C1—C2—C3—Fe1	58.9 (2)	O1'—P1—C17—C18	−158.2 (4)
C2—C3—C4—C5	−0.4 (4)	O1—P1—C17—C18	−159.6 (4)
Fe1—C3—C4—C5	−58.6 (3)	C1—P1—C17—C18	79.1 (4)
C2—C3—C4—Fe1	58.2 (3)	C11—P1—C17—C18	−41.1 (5)
C3—C4—C5—C1	1.0 (4)	C11'—P1—C17—C18	−41.6 (6)
Fe1—C4—C5—C1	−57.7 (2)	O1'—P1—C17—C22	27.6 (4)
C3—C4—C5—Fe1	58.7 (3)	O1—P1—C17—C22	26.2 (5)
C2—C1—C5—C4	−1.2 (4)	C1—P1—C17—C22	−95.1 (3)
P1—C1—C5—C4	−179.2 (3)	C11—P1—C17—C22	144.7 (4)
Fe1—C1—C5—C4	59.4 (3)	C11'—P1—C17—C22	144.2 (5)
C2—C1—C5—Fe1	−60.6 (2)	C22—C17—C18—C19	0.4 (7)
P1—C1—C5—Fe1	121.4 (2)	P1—C17—C18—C19	−173.8 (4)
C23—P2—C6—C10	14.4 (4)	C17—C18—C19—C20	−0.4 (7)
C27—P2—C6—C10	−105.5 (4)	C18—C19—C20—C21	−0.1 (8)
Cd1—P2—C6—C10	135.1 (3)	C19—C20—C21—C22	0.5 (7)
Cd1'—P2—C6—C10	134.0 (3)	C20—C21—C22—C17	−0.5 (7)
C23—P2—C6—C7	−172.2 (3)	C18—C17—C22—C21	0.0 (7)
C27—P2—C6—C7	67.9 (3)	P1—C17—C22—C21	174.4 (3)
Cd1—P2—C6—C7	−51.6 (3)	C6—P2—C23—C24	−67.3 (3)
Cd1'—P2—C6—C7	−52.6 (3)	C27—P2—C23—C24	45.7 (4)
C23—P2—C6—Fe1	−83.8 (3)	Cd1—P2—C23—C24	168.8 (3)
C27—P2—C6—Fe1	156.3 (3)	Cd1'—P2—C23—C24	173.5 (3)
Cd1—P2—C6—Fe1	36.8 (3)	C6—P2—C23—C26	56.0 (3)
Cd1'—P2—C6—Fe1	35.8 (3)	C27—P2—C23—C26	168.9 (3)
C10—C6—C7—C8	0.3 (4)	Cd1—P2—C23—C26	−68.0 (3)
P2—C6—C7—C8	−174.5 (3)	Cd1'—P2—C23—C26	−63.3 (3)
Fe1—C6—C7—C8	59.7 (2)	C6—P2—C23—C25	170.5 (3)
C10—C6—C7—Fe1	−59.3 (2)	C27—P2—C23—C25	−76.6 (4)
P2—C6—C7—Fe1	125.9 (3)	Cd1—P2—C23—C25	46.5 (3)
C6—C7—C8—C9	−0.2 (4)	Cd1'—P2—C23—C25	51.2 (3)
Fe1—C7—C8—C9	59.9 (3)	C6—P2—C27—C28	−73.7 (3)
C6—C7—C8—Fe1	−60.1 (2)	C23—P2—C27—C28	169.5 (3)
C7—C8—C9—C10	−0.1 (5)	Cd1—P2—C27—C28	47.7 (3)
Fe1—C8—C9—C10	59.1 (3)	Cd1'—P2—C27—C28	43.7 (3)
C7—C8—C9—Fe1	−59.2 (3)	C6—P2—C27—C29	45.9 (4)
C8—C9—C10—C6	0.3 (4)	C23—P2—C27—C29	−70.9 (4)
Fe1—C9—C10—C6	59.0 (3)	Cd1—P2—C27—C29	167.4 (3)
C8—C9—C10—Fe1	−58.7 (3)	Cd1'—P2—C27—C29	163.3 (3)
C7—C6—C10—C9	−0.4 (4)	C6—P2—C27—C30	169.1 (3)
P2—C6—C10—C9	173.8 (3)	C23—P2—C27—C30	52.3 (4)
Fe1—C6—C10—C9	−59.0 (3)	Cd1—P2—C27—C30	−69.4 (4)
C7—C6—C10—Fe1	58.6 (2)	Cd1'—P2—C27—C30	−73.4 (4)
P2—C6—C10—Fe1	−127.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12a—H12a···Cl2aⁱ	0.93	2.80	3.512 (7)	134
C22—H22···Cl1′b	0.93	2.94	3.836 (19)	163
C25—H25A···Cl1a	0.96	2.92	3.811 (18)	155
C26—H26A···Cl1a	0.96	2.88	3.78 (3)	156
C28—H28A···Cl2a	0.96	2.91	3.838 (5)	162

Symmetry code: (i) x−1, y, z.

Bis[µ-(tert-butyl)(1'-diphenylphosphinoylferrocen-1-yl)phosphinato-\ κ³O,O':O'']bis[chloridozinc(II)] (Complex-2) top

Crystal data top

[Zn₂{(C₉H₁₃O₂P)(C₁₇H₁₄OP)Fe}₂Cl₂]	Z = 1
M_r = 1212.17	F(000) = 620
Triclinic, P1	D_x = 1.289 Mg m⁻³
a = 10.8762 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3163 (3) Å	Cell parameters from 1320 reflections
c = 13.5343 (4) Å	θ = 3.7–27.6°
α = 83.078 (2)°	µ = 1.44 mm⁻¹
β = 87.002 (2)°	T = 293 K
γ = 70.848 (3)°	Needle, red
V = 1561.97 (8) Å³	0.40 × 0.30 × 0.10 mm

Data collection top

Rigaku Xcalibur Sapphire3 diffractometer	5000 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	R_int = 0.060
ω scans	θ_max = 29.4°, θ_min = 3.4°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −14→14
T_min = 0.148, T_max = 1.000	k = −15→15
23684 measured reflections	l = −18→18
7596 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.122	w = 1/[σ²(F_o²) + (0.0471P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
7596 reflections	Δρ_max = 0.41 e Å⁻³
335 parameters	Δρ_min = −0.37 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn1	0.47472 (3)	0.62211 (4)	0.84717 (3)	0.03308 (13)
Fe2	0.43927 (4)	0.23411 (5)	0.85665 (4)	0.03900 (15)
Cl1	0.52109 (11)	0.79161 (10)	0.78268 (8)	0.0647 (3)
P1	0.27752 (8)	0.52045 (9)	0.73127 (7)	0.0376 (2)
P2	0.67782 (8)	0.35081 (8)	0.93268 (7)	0.0330 (2)
O1	0.3875 (2)	0.5692 (2)	0.74403 (17)	0.0426 (6)
O2	0.6294 (2)	0.4785 (2)	0.87509 (18)	0.0417 (6)
O3	0.6474 (2)	0.3449 (2)	1.04217 (17)	0.0463 (6)
C1	0.2815 (3)	0.3860 (3)	0.8149 (3)	0.0367 (8)
C2	0.3032 (3)	0.3760 (3)	0.9195 (3)	0.0402 (9)
H2	0.320034	0.436030	0.952957	0.048*
C3	0.2945 (3)	0.2589 (4)	0.9628 (3)	0.0523 (11)
H3	0.303599	0.228907	1.030021	0.063*
C4	0.2699 (3)	0.1961 (4)	0.8872 (4)	0.0570 (12)
H4	0.261225	0.116406	0.895544	0.068*
C5	0.2604 (3)	0.2729 (4)	0.7965 (3)	0.0496 (10)
H5	0.243203	0.253363	0.735020	0.059*
C6	0.6211 (3)	0.2425 (3)	0.8784 (3)	0.0362 (8)
C7	0.6063 (3)	0.1295 (3)	0.9303 (3)	0.0471 (10)
H7	0.614625	0.105764	0.998429	0.057*
C8	0.5768 (4)	0.0606 (4)	0.8595 (4)	0.0678 (14)
H8	0.561187	−0.015742	0.873187	0.081*
C9	0.5752 (4)	0.1276 (4)	0.7651 (4)	0.0649 (13)
H9	0.559885	0.102334	0.705343	0.078*
C10	0.6012 (3)	0.2412 (4)	0.7764 (3)	0.0499 (10)
H10	0.604341	0.303261	0.725479	0.060*
C11	0.1246 (3)	0.6373 (4)	0.7515 (3)	0.0427 (9)
C12	0.0110 (4)	0.6064 (4)	0.7686 (3)	0.0569 (11)
H12	0.014446	0.522963	0.770728	0.068*
C13	−0.1063 (4)	0.6981 (6)	0.7826 (4)	0.0848 (18)
H13	−0.181622	0.676544	0.794863	0.102*
C14	−0.1118 (6)	0.8218 (6)	0.7783 (4)	0.104 (2)
H14	−0.191045	0.884134	0.786912	0.125*
C15	0.0001 (6)	0.8531 (5)	0.7614 (4)	0.0959 (18)
H15	−0.003747	0.936779	0.758727	0.115*
C16	0.1170 (4)	0.7617 (4)	0.7483 (3)	0.0690 (13)
H16	0.192185	0.783751	0.737231	0.083*
C17	0.2753 (8)	0.4920 (7)	0.6042 (4)	0.043 (5)	0.489 (6)
C18	0.3701 (8)	0.3898 (7)	0.5687 (7)	0.071 (4)	0.489 (6)
H18	0.432548	0.334443	0.611589	0.086*	0.489 (6)
C19	0.3715 (9)	0.3702 (7)	0.4692 (7)	0.075 (4)	0.489 (6)
H19	0.434892	0.301731	0.445448	0.089*	0.489 (6)
C20	0.2781 (10)	0.4528 (9)	0.4051 (5)	0.082 (5)	0.489 (6)
H20	0.279024	0.439726	0.338502	0.099*	0.489 (6)
C21	0.1833 (8)	0.5551 (10)	0.4406 (5)	0.111 (4)	0.489 (6)
H21	0.120812	0.610435	0.397696	0.133*	0.489 (6)
C22	0.1819 (7)	0.5747 (8)	0.5401 (5)	0.085 (4)	0.489 (6)
H22	0.118467	0.643150	0.563838	0.102*	0.489 (6)
C17'	0.2835 (7)	0.4715 (8)	0.6079 (5)	0.049 (5)	0.511 (6)
C18'	0.4006 (6)	0.4481 (9)	0.5551 (8)	0.069 (4)	0.511 (6)
H18'	0.472934	0.456146	0.583711	0.083*	0.511 (6)
C19'	0.4095 (7)	0.4128 (11)	0.4594 (8)	0.093 (5)	0.511 (6)
H19'	0.487806	0.397099	0.424055	0.112*	0.511 (6)
C20'	0.3013 (10)	0.4008 (10)	0.4166 (5)	0.099 (6)	0.511 (6)
H20'	0.307301	0.377117	0.352629	0.118*	0.511 (6)
C21'	0.1843 (7)	0.4242 (11)	0.4695 (5)	0.111 (4)	0.511 (6)
H21'	0.111921	0.416180	0.440859	0.133*	0.511 (6)
C22'	0.1754 (6)	0.4596 (10)	0.5651 (5)	0.090 (4)	0.511 (6)
H22'	0.097046	0.475226	0.600515	0.108*	0.511 (6)
C23	0.8540 (3)	0.2922 (3)	0.9160 (3)	0.0384 (8)
C24	0.8901 (3)	0.2953 (4)	0.8048 (3)	0.0639 (12)
H24A	0.856071	0.240007	0.774862	0.096*
H24B	0.983132	0.268206	0.797046	0.096*
H24C	0.853762	0.379492	0.773077	0.096*
C25	0.9086 (3)	0.1572 (4)	0.9670 (4)	0.0681 (13)
H25A	0.882639	0.155297	1.035910	0.102*
H25B	1.001853	0.128976	0.961834	0.102*
H25C	0.875331	0.102779	0.935132	0.102*
C26	0.9126 (3)	0.3775 (4)	0.9639 (3)	0.0516 (10)
H26A	0.874965	0.462867	0.934755	0.077*
H26B	1.005084	0.350603	0.952692	0.077*
H26C	0.894395	0.372443	1.034154	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0306 (2)	0.0296 (2)	0.0382 (2)	−0.00814 (17)	−0.00107 (16)	−0.00472 (18)
Fe2	0.0314 (3)	0.0322 (3)	0.0542 (4)	−0.0083 (2)	−0.0004 (2)	−0.0133 (3)
Cl1	0.0856 (8)	0.0459 (6)	0.0722 (8)	−0.0365 (6)	−0.0026 (6)	0.0009 (6)
P1	0.0346 (5)	0.0438 (6)	0.0346 (5)	−0.0115 (4)	−0.0035 (4)	−0.0076 (5)
P2	0.0257 (4)	0.0296 (5)	0.0419 (5)	−0.0050 (4)	0.0015 (4)	−0.0093 (4)
O1	0.0425 (14)	0.0533 (16)	0.0376 (14)	−0.0231 (12)	−0.0018 (11)	−0.0054 (12)
O2	0.0341 (13)	0.0278 (13)	0.0593 (16)	−0.0054 (11)	−0.0038 (11)	−0.0016 (12)
O3	0.0404 (14)	0.0521 (16)	0.0441 (15)	−0.0108 (12)	0.0074 (11)	−0.0121 (13)
C1	0.0272 (17)	0.041 (2)	0.042 (2)	−0.0087 (15)	−0.0012 (15)	−0.0121 (18)
C2	0.0390 (19)	0.035 (2)	0.042 (2)	−0.0043 (16)	0.0019 (16)	−0.0099 (18)
C3	0.036 (2)	0.050 (3)	0.060 (3)	−0.0049 (19)	0.0069 (18)	0.004 (2)
C4	0.038 (2)	0.038 (2)	0.096 (4)	−0.0161 (18)	−0.002 (2)	−0.001 (2)
C5	0.039 (2)	0.049 (2)	0.066 (3)	−0.0167 (19)	−0.0108 (19)	−0.016 (2)
C6	0.0279 (17)	0.0322 (19)	0.046 (2)	−0.0042 (15)	0.0020 (15)	−0.0098 (17)
C7	0.036 (2)	0.030 (2)	0.069 (3)	−0.0022 (16)	−0.0056 (18)	−0.005 (2)
C8	0.041 (2)	0.034 (2)	0.127 (5)	−0.0051 (19)	0.003 (3)	−0.027 (3)
C9	0.042 (2)	0.069 (3)	0.090 (4)	−0.011 (2)	0.007 (2)	−0.060 (3)
C10	0.034 (2)	0.063 (3)	0.056 (3)	−0.0152 (19)	0.0095 (17)	−0.025 (2)
C11	0.039 (2)	0.049 (2)	0.032 (2)	−0.0028 (18)	−0.0024 (15)	−0.0016 (18)
C12	0.041 (2)	0.077 (3)	0.047 (2)	−0.008 (2)	0.0006 (18)	−0.015 (2)
C13	0.034 (2)	0.132 (5)	0.065 (3)	0.005 (3)	0.001 (2)	−0.016 (4)
C14	0.066 (4)	0.102 (5)	0.090 (4)	0.046 (4)	−0.002 (3)	−0.008 (4)
C15	0.088 (4)	0.056 (3)	0.110 (5)	0.022 (3)	−0.001 (3)	−0.007 (3)
C16	0.064 (3)	0.057 (3)	0.076 (3)	−0.006 (2)	−0.005 (2)	−0.004 (3)
C17	0.044 (9)	0.061 (8)	0.022 (8)	−0.012 (6)	0.005 (6)	−0.017 (6)
C18	0.073 (8)	0.080 (9)	0.051 (7)	0.004 (6)	−0.018 (6)	−0.039 (7)
C19	0.087 (9)	0.085 (9)	0.041 (7)	−0.007 (8)	0.004 (6)	−0.027 (6)
C20	0.103 (11)	0.103 (11)	0.039 (7)	−0.021 (8)	−0.006 (7)	−0.034 (7)
C21	0.093 (5)	0.196 (12)	0.043 (5)	−0.037 (8)	−0.015 (4)	−0.033 (6)
C22	0.083 (7)	0.104 (10)	0.041 (6)	0.008 (7)	−0.016 (5)	−0.008 (6)
C17'	0.050 (10)	0.053 (7)	0.054 (11)	−0.032 (7)	−0.008 (8)	0.001 (6)
C18'	0.061 (6)	0.106 (10)	0.048 (6)	−0.030 (6)	0.005 (5)	−0.026 (7)
C19'	0.078 (8)	0.148 (14)	0.066 (8)	−0.052 (8)	0.015 (6)	−0.025 (9)
C20'	0.083 (10)	0.153 (15)	0.056 (9)	−0.020 (10)	0.007 (8)	−0.051 (9)
C21'	0.093 (5)	0.196 (12)	0.043 (5)	−0.037 (8)	−0.015 (4)	−0.033 (6)
C22'	0.058 (6)	0.174 (13)	0.053 (6)	−0.048 (7)	−0.003 (5)	−0.043 (8)
C23	0.0256 (17)	0.035 (2)	0.052 (2)	−0.0045 (15)	0.0014 (15)	−0.0092 (18)
C24	0.036 (2)	0.089 (3)	0.067 (3)	−0.018 (2)	0.0129 (19)	−0.026 (3)
C25	0.037 (2)	0.046 (3)	0.107 (4)	0.0033 (19)	−0.004 (2)	0.001 (3)
C26	0.0320 (19)	0.062 (3)	0.059 (3)	−0.0098 (19)	0.0034 (17)	−0.017 (2)

Geometric parameters (Å, º) top

Zn1—O2	1.934 (2)	C12—C13	1.377 (6)
Zn1—O3ⁱ	1.936 (2)	C12—H12	0.9300
Zn1—O1	1.980 (2)	C13—C14	1.375 (8)
Zn1—Cl1	2.2092 (10)	C13—H13	0.9300
Fe2—C2	2.032 (3)	C14—C15	1.376 (7)
Fe2—C4	2.036 (4)	C14—H14	0.9300
Fe2—C1	2.037 (3)	C15—C16	1.370 (6)
Fe2—C8	2.038 (4)	C15—H15	0.9300
Fe2—C5	2.039 (3)	C16—H16	0.9300
Fe2—C10	2.040 (3)	C17—C18	1.3900
Fe2—C9	2.043 (4)	C17—C22	1.3900
Fe2—C7	2.046 (3)	C18—C19	1.3900
Fe2—C3	2.048 (4)	C18—H18	0.9300
Fe2—C6	2.048 (3)	C19—C20	1.3900
P1—O1	1.498 (2)	C19—H19	0.9300
P1—C1	1.773 (4)	C20—C21	1.3900
P1—C11	1.785 (4)	C20—H20	0.9300
P1—C17	1.790 (6)	C21—C22	1.3900
P1—C17'	1.812 (6)	C21—H21	0.9300
P2—O2	1.498 (2)	C22—H22	0.9300
P2—O3	1.500 (2)	C17'—C18'	1.3900
P2—C6	1.785 (4)	C17'—C22'	1.3900
P2—C23	1.822 (3)	C18'—C19'	1.3900
C1—C5	1.424 (5)	C18'—H18'	0.9300
C1—C2	1.431 (5)	C19'—C20'	1.3900
C2—C3	1.414 (5)	C19'—H19'	0.9300
C2—H2	0.9300	C20'—C21'	1.3900
C3—C4	1.398 (5)	C20'—H20'	0.9300
C3—H3	0.9300	C21'—C22'	1.3900
C4—C5	1.403 (5)	C21'—H21'	0.9300
C4—H4	0.9300	C22'—H22'	0.9300
C5—H5	0.9300	C23—C24	1.534 (5)
C6—C10	1.411 (5)	C23—C25	1.535 (5)
C6—C7	1.435 (5)	C23—C26	1.535 (5)
C7—C8	1.416 (5)	C24—H24A	0.9600
C7—H7	0.9300	C24—H24B	0.9600
C8—C9	1.402 (6)	C24—H24C	0.9600
C8—H8	0.9300	C25—H25A	0.9600
C9—C10	1.431 (5)	C25—H25B	0.9600
C9—H9	0.9300	C25—H25C	0.9600
C10—H10	0.9300	C26—H26A	0.9600
C11—C16	1.379 (6)	C26—H26B	0.9600
C11—C12	1.390 (5)	C26—H26C	0.9600

O2—Zn1—O3ⁱ	114.14 (10)	P2—C6—Fe2	133.24 (18)
O2—Zn1—O1	103.13 (10)	C8—C7—C6	108.0 (4)
O3ⁱ—Zn1—O1	106.03 (10)	C8—C7—Fe2	69.4 (2)
O2—Zn1—Cl1	112.26 (7)	C6—C7—Fe2	69.56 (19)
O3ⁱ—Zn1—Cl1	112.38 (8)	C8—C7—H7	126.0
O1—Zn1—Cl1	108.08 (7)	C6—C7—H7	126.0
C2—Fe2—C4	68.05 (16)	Fe2—C7—H7	126.6
C2—Fe2—C1	41.19 (13)	C9—C8—C7	108.1 (4)
C4—Fe2—C1	68.47 (14)	C9—C8—Fe2	70.1 (2)
C2—Fe2—C8	154.01 (19)	C7—C8—Fe2	70.0 (2)
C4—Fe2—C8	103.82 (16)	C9—C8—H8	125.9
C1—Fe2—C8	160.77 (17)	C7—C8—H8	125.9
C2—Fe2—C5	68.50 (15)	Fe2—C8—H8	125.5
C4—Fe2—C5	40.27 (14)	C8—C9—C10	108.5 (4)
C1—Fe2—C5	40.91 (13)	C8—C9—Fe2	69.7 (2)
C8—Fe2—C5	122.09 (17)	C10—C9—Fe2	69.4 (2)
C2—Fe2—C10	127.99 (15)	C8—C9—H9	125.8
C4—Fe2—C10	156.93 (18)	C10—C9—H9	125.8
C1—Fe2—C10	111.24 (15)	Fe2—C9—H9	126.7
C8—Fe2—C10	68.61 (17)	C6—C10—C9	107.8 (4)
C5—Fe2—C10	124.13 (16)	C6—C10—Fe2	70.1 (2)
C2—Fe2—C9	165.26 (19)	C9—C10—Fe2	69.6 (2)
C4—Fe2—C9	119.38 (17)	C6—C10—H10	126.1
C1—Fe2—C9	126.99 (18)	C9—C10—H10	126.1
C8—Fe2—C9	40.18 (16)	Fe2—C10—H10	125.7
C5—Fe2—C9	108.18 (17)	C16—C11—C12	118.6 (4)
C10—Fe2—C9	41.04 (16)	C16—C11—P1	119.8 (3)
C2—Fe2—C7	120.90 (15)	C12—C11—P1	121.6 (3)
C4—Fe2—C7	120.82 (16)	C13—C12—C11	120.7 (5)
C1—Fe2—C7	158.52 (15)	C13—C12—H12	119.7
C8—Fe2—C7	40.57 (15)	C11—C12—H12	119.7
C5—Fe2—C7	157.57 (15)	C14—C13—C12	119.7 (5)
C10—Fe2—C7	68.37 (16)	C14—C13—H13	120.1
C9—Fe2—C7	67.83 (17)	C12—C13—H13	120.1
C2—Fe2—C3	40.54 (14)	C13—C14—C15	120.0 (5)
C4—Fe2—C3	40.04 (15)	C13—C14—H14	120.0
C1—Fe2—C3	68.60 (14)	C15—C14—H14	120.0
C8—Fe2—C3	117.53 (19)	C16—C15—C14	120.3 (5)
C5—Fe2—C3	67.77 (16)	C16—C15—H15	119.9
C10—Fe2—C3	162.89 (17)	C14—C15—H15	119.9
C9—Fe2—C3	152.94 (19)	C15—C16—C11	120.7 (5)
C7—Fe2—C3	105.20 (16)	C15—C16—H16	119.6
C2—Fe2—C6	109.61 (14)	C11—C16—H16	119.6
C4—Fe2—C6	159.01 (16)	C18—C17—C22	120.0
C1—Fe2—C6	124.51 (14)	C18—C17—P1	119.9 (5)
C8—Fe2—C6	68.73 (15)	C22—C17—P1	120.1 (5)
C5—Fe2—C6	160.11 (15)	C17—C18—C19	120.0
C10—Fe2—C6	40.39 (14)	C17—C18—H18	120.0
C9—Fe2—C6	68.31 (14)	C19—C18—H18	120.0
C7—Fe2—C6	41.02 (13)	C20—C19—C18	120.0
C3—Fe2—C6	124.57 (16)	C20—C19—H19	120.0
O1—P1—C1	113.66 (14)	C18—C19—H19	120.0
O1—P1—C11	110.78 (17)	C19—C20—C21	120.0
C1—P1—C11	106.38 (16)	C19—C20—H20	120.0
O1—P1—C17	108.8 (3)	C21—C20—H20	120.0
C1—P1—C17	111.9 (3)	C22—C21—C20	120.0
C11—P1—C17	105.0 (3)	C22—C21—H21	120.0
O1—P1—C17'	110.4 (3)	C20—C21—H21	120.0
C1—P1—C17'	105.4 (3)	C21—C22—C17	120.0
C11—P1—C17'	109.9 (3)	C21—C22—H22	120.0
O2—P2—O3	116.01 (14)	C17—C22—H22	120.0
O2—P2—C6	110.16 (15)	C18'—C17'—C22'	120.0
O3—P2—C6	109.75 (16)	C18'—C17'—P1	117.8 (5)
O2—P2—C23	107.44 (15)	C22'—C17'—P1	122.2 (5)
O3—P2—C23	108.32 (15)	C17'—C18'—C19'	120.0
C6—P2—C23	104.49 (16)	C17'—C18'—H18'	120.0
P1—O1—Zn1	141.30 (15)	C19'—C18'—H18'	120.0
P2—O2—Zn1	142.92 (15)	C20'—C19'—C18'	120.0
P2—O3—Zn1ⁱ	151.38 (15)	C20'—C19'—H19'	120.0
C5—C1—C2	106.7 (3)	C18'—C19'—H19'	120.0
C5—C1—P1	129.6 (3)	C19'—C20'—C21'	120.0
C2—C1—P1	123.7 (3)	C19'—C20'—H20'	120.0
C5—C1—Fe2	69.6 (2)	C21'—C20'—H20'	120.0
C2—C1—Fe2	69.22 (18)	C22'—C21'—C20'	120.0
P1—C1—Fe2	127.80 (17)	C22'—C21'—H21'	120.0
C3—C2—C1	108.0 (3)	C20'—C21'—H21'	120.0
C3—C2—Fe2	70.3 (2)	C21'—C22'—C17'	120.0
C1—C2—Fe2	69.59 (19)	C21'—C22'—H22'	120.0
C3—C2—H2	126.0	C17'—C22'—H22'	120.0
C1—C2—H2	126.0	C24—C23—C25	109.9 (3)
Fe2—C2—H2	125.7	C24—C23—C26	109.0 (3)
C4—C3—C2	108.1 (4)	C25—C23—C26	109.3 (3)
C4—C3—Fe2	69.5 (2)	C24—C23—P2	110.3 (2)
C2—C3—Fe2	69.1 (2)	C25—C23—P2	109.9 (2)
C4—C3—H3	125.9	C26—C23—P2	108.4 (2)
C2—C3—H3	125.9	C23—C24—H24A	109.5
Fe2—C3—H3	127.0	C23—C24—H24B	109.5
C3—C4—C5	108.9 (3)	H24A—C24—H24B	109.5
C3—C4—Fe2	70.4 (2)	C23—C24—H24C	109.5
C5—C4—Fe2	70.0 (2)	H24A—C24—H24C	109.5
C3—C4—H4	125.6	H24B—C24—H24C	109.5
C5—C4—H4	125.6	C23—C25—H25A	109.5
Fe2—C4—H4	125.6	C23—C25—H25B	109.5
C4—C5—C1	108.3 (3)	H25A—C25—H25B	109.5
C4—C5—Fe2	69.8 (2)	C23—C25—H25C	109.5
C1—C5—Fe2	69.46 (19)	H25A—C25—H25C	109.5
C4—C5—H5	125.9	H25B—C25—H25C	109.5
C1—C5—H5	125.9	C23—C26—H26A	109.5
Fe2—C5—H5	126.5	C23—C26—H26B	109.5
C10—C6—C7	107.5 (3)	H26A—C26—H26B	109.5
C10—C6—P2	126.9 (3)	C23—C26—H26C	109.5
C7—C6—P2	124.9 (3)	H26A—C26—H26C	109.5
C10—C6—Fe2	69.47 (19)	H26B—C26—H26C	109.5
C7—C6—Fe2	69.41 (19)

C1—P1—O1—Zn1	−52.3 (3)	C7—C6—C10—C9	−0.5 (4)
C11—P1—O1—Zn1	67.5 (3)	P2—C6—C10—C9	171.0 (3)
C17—P1—O1—Zn1	−177.7 (3)	Fe2—C6—C10—C9	−59.6 (2)
C17'—P1—O1—Zn1	−170.5 (4)	C7—C6—C10—Fe2	59.2 (2)
O3—P2—O2—Zn1	−53.6 (3)	P2—C6—C10—Fe2	−129.3 (3)
C6—P2—O2—Zn1	71.9 (3)	C8—C9—C10—C6	1.0 (4)
C23—P2—O2—Zn1	−174.9 (2)	Fe2—C9—C10—C6	60.0 (2)
O2—P2—O3—Zn1ⁱ	54.1 (4)	C8—C9—C10—Fe2	−58.9 (3)
C6—P2—O3—Zn1ⁱ	−71.5 (4)	O1—P1—C11—C16	17.6 (4)
C23—P2—O3—Zn1ⁱ	174.9 (3)	C1—P1—C11—C16	141.6 (3)
O1—P1—C1—C5	−136.0 (3)	C17—P1—C11—C16	−99.6 (4)
C11—P1—C1—C5	101.8 (3)	C17'—P1—C11—C16	−104.7 (4)
C17—P1—C1—C5	−12.3 (5)	O1—P1—C11—C12	−163.6 (3)
C17'—P1—C1—C5	−14.9 (4)	C1—P1—C11—C12	−39.6 (3)
O1—P1—C1—C2	46.7 (3)	C17—P1—C11—C12	79.2 (4)
C11—P1—C1—C2	−75.5 (3)	C17'—P1—C11—C12	74.1 (4)
C17—P1—C1—C2	170.4 (4)	C16—C11—C12—C13	−0.2 (6)
C17'—P1—C1—C2	167.8 (3)	P1—C11—C12—C13	−179.0 (3)
O1—P1—C1—Fe2	−42.0 (3)	C11—C12—C13—C14	0.8 (7)
C11—P1—C1—Fe2	−164.2 (2)	C12—C13—C14—C15	−0.8 (9)
C17—P1—C1—Fe2	81.7 (4)	C13—C14—C15—C16	0.2 (9)
C17'—P1—C1—Fe2	79.0 (3)	C14—C15—C16—C11	0.3 (8)
C5—C1—C2—C3	−0.2 (4)	C12—C11—C16—C15	−0.3 (7)
P1—C1—C2—C3	177.6 (2)	P1—C11—C16—C15	178.5 (4)
Fe2—C1—C2—C3	−60.1 (2)	O1—P1—C17—C18	72.9 (5)
C5—C1—C2—Fe2	59.8 (2)	C1—P1—C17—C18	−53.5 (5)
P1—C1—C2—Fe2	−122.3 (2)	C11—P1—C17—C18	−168.5 (5)
C1—C2—C3—C4	0.8 (4)	O1—P1—C17—C22	−104.6 (5)
Fe2—C2—C3—C4	−58.8 (3)	C1—P1—C17—C22	128.9 (5)
C1—C2—C3—Fe2	59.6 (2)	C11—P1—C17—C22	14.0 (5)
C2—C3—C4—C5	−1.1 (4)	C22—C17—C18—C19	0.0
Fe2—C3—C4—C5	−59.6 (3)	P1—C17—C18—C19	−177.6 (6)
C2—C3—C4—Fe2	58.5 (2)	C17—C18—C19—C20	0.0
C3—C4—C5—C1	1.0 (4)	C18—C19—C20—C21	0.0
Fe2—C4—C5—C1	−59.0 (2)	C19—C20—C21—C22	0.0
C3—C4—C5—Fe2	59.9 (3)	C20—C21—C22—C17	0.0
C2—C1—C5—C4	−0.4 (4)	C18—C17—C22—C21	0.0
P1—C1—C5—C4	−178.1 (3)	P1—C17—C22—C21	177.6 (6)
Fe2—C1—C5—C4	59.1 (2)	O1—P1—C17'—C18'	18.9 (6)
C2—C1—C5—Fe2	−59.6 (2)	C1—P1—C17'—C18'	−104.2 (5)
P1—C1—C5—Fe2	122.8 (3)	C11—P1—C17'—C18'	141.5 (5)
O2—P2—C6—C10	34.0 (3)	O1—P1—C17'—C22'	−159.8 (5)
O3—P2—C6—C10	162.9 (3)	C1—P1—C17'—C22'	77.1 (5)
C23—P2—C6—C10	−81.2 (3)	C11—P1—C17'—C22'	−37.2 (6)
O2—P2—C6—C7	−155.9 (3)	C22'—C17'—C18'—C19'	0.0
O3—P2—C6—C7	−27.0 (3)	P1—C17'—C18'—C19'	−178.8 (7)
C23—P2—C6—C7	88.9 (3)	C17'—C18'—C19'—C20'	0.0
O2—P2—C6—Fe2	−62.0 (3)	C18'—C19'—C20'—C21'	0.0
O3—P2—C6—Fe2	66.9 (3)	C19'—C20'—C21'—C22'	0.0
C23—P2—C6—Fe2	−177.2 (2)	C20'—C21'—C22'—C17'	0.0
C10—C6—C7—C8	−0.3 (4)	C18'—C17'—C22'—C21'	0.0
P2—C6—C7—C8	−172.0 (2)	P1—C17'—C22'—C21'	178.7 (7)
Fe2—C6—C7—C8	58.9 (2)	O2—P2—C23—C24	−54.5 (3)
C10—C6—C7—Fe2	−59.2 (2)	O3—P2—C23—C24	179.5 (3)
P2—C6—C7—Fe2	129.1 (3)	C6—P2—C23—C24	62.6 (3)
C6—C7—C8—C9	1.0 (4)	O2—P2—C23—C25	−175.8 (3)
Fe2—C7—C8—C9	60.0 (3)	O3—P2—C23—C25	58.2 (3)
C6—C7—C8—Fe2	−59.0 (2)	C6—P2—C23—C25	−58.8 (3)
C7—C8—C9—C10	−1.2 (4)	O2—P2—C23—C26	64.8 (3)
Fe2—C8—C9—C10	58.7 (3)	O3—P2—C23—C26	−61.2 (3)
C7—C8—C9—Fe2	−59.9 (3)	C6—P2—C23—C26	−178.1 (2)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3ⁱ	0.93	2.63	3.474 (5)	152

Symmetry code: (i) −x+1, −y+1, −z+2.

1,1'-Bis(di-tert-butylthiophosphinoyl)ferrocene (Complex-3) top

Crystal data top

[Fe(C₁₃H₂₂PS)₂]	F(000) = 1152
M_r = 538.52	D_x = 1.316 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.7589 (7) Å	Cell parameters from 5962 reflections
b = 14.0445 (5) Å	θ = 2.8–27.5°
c = 14.7141 (6) Å	µ = 0.84 mm⁻¹
β = 116.9816 (18)°	T = 100 K
V = 2718.0 (2) Å³	Rectangular, yellow
Z = 4	0.17 × 0.06 × 0.05 mm

Data collection top

Bruker D8 VENTURE diffractometer	6228 independent reflections
Radiation source: microfocus sealed tube	4652 reflections with I > 2σ(I)
Detector resolution: 7.41 pixels mm^-1	R_int = 0.082
ω and φ scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −19→19
T_min = 0.768, T_max = 0.888	k = −17→18
26174 measured reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.095	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0171P)² + 1.5394P] where P = (F_o² + 2F_c²)/3
6228 reflections	(Δ/σ)_max = 0.001
292 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Special details top

Refinement. All H atoms were positioned geometrically and refined using a riding model with C—H = 0.95–0.99 Å and with U_iso(H) = 1.2 (1.5 for methyl groups) times U_eq(C).

Intensity data sets for 1 and 2 were collected on a X-calibur-S Oxford CCD area detector diffractometer using graphite monochromated Mo-K? radiation at 293 (2) K. Intensity data sets for 3 and 4 were collected on a Bruker APEX II CCD area detector diffractometer using graphite monochromated Mo-K? radiation at 100 (2) and 100 (2) K. CrysAlisPro RED and Apex2, software packages were used for data collection and data integration for 1, 2 (Rigaku Oxford Diffraction, 2015)and 3, 4 ?(Bruker, 2009)?. The structures were solved by direct methods using SHELXS-97, and refined by full matrix least-squares with SHELXL-2014 ?(Sheldrick, 2015)?. The non-hydrogen atoms were refined with anisotropic thermal parameters.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Fe1	0.32293 (3)	0.78597 (2)	0.37208 (3)	0.01410 (10)
S1	0.00866 (5)	0.78738 (5)	0.18404 (5)	0.02396 (16)
S2	0.63003 (5)	0.80465 (5)	0.57177 (5)	0.02486 (16)
P1	0.07600 (5)	0.68161 (4)	0.27710 (5)	0.01384 (14)
P2	0.58286 (5)	0.77944 (4)	0.42623 (5)	0.01379 (14)
C1	0.20211 (18)	0.71390 (16)	0.37280 (19)	0.0129 (5)
C2	0.2211 (2)	0.80201 (17)	0.4282 (2)	0.0187 (5)
H2	0.174383	0.853155	0.413105	0.022*
C3	0.3212 (2)	0.79979 (18)	0.5091 (2)	0.0206 (6)
H3	0.352913	0.849088	0.557492	0.025*
C4	0.3660 (2)	0.71192 (18)	0.50573 (19)	0.0184 (5)
H4	0.432909	0.691904	0.551216	0.022*
C5	0.29351 (19)	0.65867 (17)	0.42240 (19)	0.0146 (5)
H5	0.303800	0.596759	0.402744	0.018*
C6	0.45007 (19)	0.81032 (16)	0.3528 (2)	0.0156 (5)
C7	0.4105 (2)	0.89738 (17)	0.3719 (2)	0.0198 (6)
H7	0.445911	0.939503	0.427365	0.024*
C8	0.3098 (2)	0.90987 (19)	0.2939 (2)	0.0259 (7)
H8	0.266421	0.961990	0.287919	0.031*
C9	0.2851 (2)	0.8317 (2)	0.2268 (2)	0.0237 (6)
H9	0.222076	0.821796	0.167965	0.028*
C10	0.37081 (19)	0.77019 (18)	0.2624 (2)	0.0181 (5)
H10	0.374809	0.712129	0.231254	0.022*
C11	0.0870 (2)	0.57699 (17)	0.2041 (2)	0.0177 (5)
C12	0.1235 (2)	0.48569 (17)	0.2677 (2)	0.0236 (6)
H12A	0.183674	0.499788	0.331974	0.035*
H12B	0.140794	0.437926	0.229554	0.035*
H12C	0.069284	0.461023	0.282201	0.035*
C13	−0.0160 (2)	0.5585 (2)	0.1117 (2)	0.0291 (7)
H13A	−0.067145	0.545073	0.135144	0.044*
H13B	−0.010251	0.503830	0.073325	0.044*
H13C	−0.036411	0.614918	0.067706	0.044*
C14	0.1625 (2)	0.60455 (18)	0.1630 (2)	0.0209 (6)
H14A	0.143646	0.666705	0.129229	0.031*
H14B	0.160593	0.556498	0.113823	0.031*
H14C	0.231308	0.607995	0.219609	0.031*
C15	0.01142 (19)	0.64899 (18)	0.3581 (2)	0.0179 (5)
C16	−0.0116 (2)	0.74234 (19)	0.3977 (2)	0.0257 (6)
H16A	0.052140	0.776237	0.438759	0.039*
H16B	−0.045693	0.728224	0.439859	0.039*
H16C	−0.055882	0.782187	0.339864	0.039*
C17	0.0795 (2)	0.58755 (19)	0.4500 (2)	0.0231 (6)
H17A	0.089274	0.525004	0.426287	0.035*
H17B	0.047168	0.579614	0.494850	0.035*
H17C	0.145595	0.618770	0.487760	0.035*
C18	−0.0901 (2)	0.5978 (2)	0.2946 (2)	0.0283 (7)
H18A	−0.131090	0.635084	0.233285	0.043*
H18B	−0.126992	0.590913	0.335340	0.043*
H18C	−0.076872	0.534625	0.274870	0.043*
C19	0.6026 (2)	0.65151 (17)	0.4025 (2)	0.0189 (6)
C20	0.7103 (2)	0.6202 (2)	0.4790 (2)	0.0290 (7)
H20A	0.760328	0.653315	0.463829	0.044*
H20B	0.717185	0.551316	0.473580	0.044*
H20C	0.722117	0.636077	0.548380	0.044*
C21	0.5272 (2)	0.59200 (18)	0.4251 (2)	0.0258 (6)
H21A	0.536041	0.606938	0.493741	0.039*
H21B	0.540134	0.524091	0.421020	0.039*
H21C	0.457414	0.607189	0.374956	0.039*
C22	0.5862 (2)	0.63036 (18)	0.2944 (2)	0.0241 (6)
H22A	0.518668	0.652628	0.245308	0.036*
H22B	0.591304	0.561597	0.286363	0.036*
H22C	0.638212	0.663274	0.282167	0.036*
C23	0.64613 (19)	0.86122 (17)	0.3714 (2)	0.0170 (5)
C24	0.5871 (2)	0.86787 (18)	0.2547 (2)	0.0213 (6)
H24A	0.582299	0.804493	0.224999	0.032*
H24B	0.622762	0.910940	0.229348	0.032*
H24C	0.518633	0.892412	0.235374	0.032*
C25	0.6495 (2)	0.96075 (18)	0.4154 (2)	0.0255 (6)
H25A	0.580033	0.982918	0.395286	0.038*
H25B	0.683516	1.004789	0.389114	0.038*
H25C	0.687119	0.958214	0.489963	0.038*
C26	0.7556 (2)	0.82904 (19)	0.4034 (2)	0.0234 (6)
H26A	0.789497	0.816031	0.476822	0.035*
H26B	0.792337	0.879422	0.387772	0.035*
H26C	0.755053	0.771069	0.366071	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.01442 (19)	0.01378 (17)	0.0154 (2)	−0.00132 (14)	0.00786 (16)	0.00134 (14)
S1	0.0243 (4)	0.0257 (3)	0.0222 (4)	0.0112 (3)	0.0107 (3)	0.0066 (3)
S2	0.0234 (4)	0.0368 (4)	0.0136 (3)	−0.0083 (3)	0.0077 (3)	−0.0031 (3)
P1	0.0125 (3)	0.0158 (3)	0.0135 (3)	0.0013 (2)	0.0062 (3)	−0.0004 (2)
P2	0.0134 (3)	0.0151 (3)	0.0125 (3)	−0.0020 (2)	0.0056 (3)	−0.0002 (2)
C1	0.0135 (12)	0.0145 (11)	0.0123 (12)	−0.0014 (9)	0.0071 (10)	−0.0008 (10)
C2	0.0224 (14)	0.0170 (12)	0.0229 (15)	−0.0034 (10)	0.0155 (12)	−0.0029 (11)
C3	0.0258 (15)	0.0234 (13)	0.0156 (14)	−0.0103 (11)	0.0121 (12)	−0.0041 (11)
C4	0.0182 (13)	0.0247 (13)	0.0104 (13)	−0.0036 (10)	0.0049 (11)	0.0030 (10)
C5	0.0168 (13)	0.0143 (12)	0.0148 (13)	−0.0017 (9)	0.0089 (11)	0.0026 (9)
C6	0.0162 (13)	0.0142 (11)	0.0203 (14)	−0.0014 (9)	0.0118 (11)	0.0031 (10)
C7	0.0205 (14)	0.0141 (12)	0.0302 (16)	−0.0031 (10)	0.0163 (13)	0.0027 (11)
C8	0.0236 (15)	0.0201 (13)	0.0398 (19)	0.0070 (11)	0.0195 (14)	0.0164 (12)
C9	0.0153 (14)	0.0356 (16)	0.0185 (15)	0.0005 (11)	0.0062 (12)	0.0147 (12)
C10	0.0172 (13)	0.0235 (13)	0.0158 (13)	−0.0025 (10)	0.0092 (11)	0.0018 (10)
C11	0.0187 (14)	0.0197 (12)	0.0157 (14)	−0.0011 (10)	0.0086 (12)	−0.0054 (10)
C12	0.0297 (16)	0.0152 (12)	0.0271 (16)	−0.0022 (11)	0.0139 (14)	−0.0033 (11)
C13	0.0227 (16)	0.0408 (17)	0.0200 (16)	−0.0027 (12)	0.0065 (13)	−0.0110 (13)
C14	0.0239 (15)	0.0224 (13)	0.0196 (15)	0.0031 (11)	0.0127 (13)	−0.0033 (11)
C15	0.0139 (13)	0.0254 (13)	0.0159 (14)	−0.0026 (10)	0.0081 (11)	−0.0024 (10)
C16	0.0249 (15)	0.0301 (15)	0.0297 (17)	0.0019 (12)	0.0190 (14)	−0.0026 (12)
C17	0.0228 (15)	0.0303 (15)	0.0196 (15)	−0.0012 (11)	0.0126 (13)	0.0034 (12)
C18	0.0194 (15)	0.0386 (16)	0.0293 (17)	−0.0064 (12)	0.0130 (14)	−0.0040 (13)
C19	0.0204 (14)	0.0123 (11)	0.0235 (15)	0.0021 (10)	0.0095 (12)	0.0028 (10)
C20	0.0249 (16)	0.0257 (14)	0.0329 (18)	0.0067 (12)	0.0100 (14)	0.0121 (13)
C21	0.0301 (16)	0.0154 (13)	0.0374 (18)	−0.0014 (11)	0.0203 (15)	0.0029 (12)
C22	0.0304 (16)	0.0178 (13)	0.0287 (17)	0.0006 (11)	0.0174 (14)	−0.0062 (11)
C23	0.0186 (14)	0.0168 (12)	0.0186 (14)	−0.0011 (10)	0.0111 (12)	0.0019 (10)
C24	0.0233 (15)	0.0219 (13)	0.0214 (15)	0.0015 (11)	0.0127 (13)	0.0062 (11)
C25	0.0281 (16)	0.0175 (13)	0.0380 (18)	−0.0080 (11)	0.0211 (15)	−0.0044 (12)
C26	0.0178 (14)	0.0252 (14)	0.0298 (17)	−0.0044 (11)	0.0131 (13)	0.0011 (12)

Geometric parameters (Å, º) top

Fe1—C2	2.029 (2)	C13—H13A	0.9800
Fe1—C7	2.031 (2)	C13—H13B	0.9800
Fe1—C3	2.037 (3)	C13—H13C	0.9800
Fe1—C8	2.046 (3)	C14—H14A	0.9800
Fe1—C10	2.047 (3)	C14—H14B	0.9800
Fe1—C6	2.049 (2)	C14—H14C	0.9800
Fe1—C9	2.052 (3)	C15—C17	1.533 (4)
Fe1—C4	2.054 (2)	C15—C16	1.534 (4)
Fe1—C1	2.055 (2)	C15—C18	1.538 (4)
Fe1—C5	2.056 (2)	C16—H16A	0.9800
S1—P1	1.9581 (9)	C16—H16B	0.9800
S2—P2	1.9604 (10)	C16—H16C	0.9800
P1—C1	1.810 (3)	C17—H17A	0.9800
P1—C11	1.870 (2)	C17—H17B	0.9800
P1—C15	1.889 (3)	C17—H17C	0.9800
P2—C6	1.810 (3)	C18—H18A	0.9800
P2—C23	1.878 (2)	C18—H18B	0.9800
P2—C19	1.878 (2)	C18—H18C	0.9800
C1—C5	1.436 (3)	C19—C22	1.526 (4)
C1—C2	1.438 (3)	C19—C20	1.538 (4)
C2—C3	1.416 (4)	C19—C21	1.544 (3)
C2—H2	0.9500	C20—H20A	0.9800
C3—C4	1.411 (4)	C20—H20B	0.9800
C3—H3	0.9500	C20—H20C	0.9800
C4—C5	1.420 (3)	C21—H21A	0.9800
C4—H4	0.9500	C21—H21B	0.9800
C5—H5	0.9500	C21—H21C	0.9800
C6—C10	1.430 (4)	C22—H22A	0.9800
C6—C7	1.436 (3)	C22—H22B	0.9800
C7—C8	1.417 (4)	C22—H22C	0.9800
C7—H7	0.9500	C23—C25	1.532 (3)
C8—C9	1.410 (4)	C23—C26	1.532 (4)
C8—H8	0.9500	C23—C24	1.535 (4)
C9—C10	1.421 (4)	C24—H24A	0.9800
C9—H9	0.9500	C24—H24B	0.9800
C10—H10	0.9500	C24—H24C	0.9800
C11—C13	1.533 (4)	C25—H25A	0.9800
C11—C12	1.534 (4)	C25—H25B	0.9800
C11—C14	1.539 (3)	C25—H25C	0.9800
C12—H12A	0.9800	C26—H26A	0.9800
C12—H12B	0.9800	C26—H26B	0.9800
C12—H12C	0.9800	C26—H26C	0.9800

C2—Fe1—C7	120.31 (10)	C10—C9—Fe1	69.51 (15)
C2—Fe1—C3	40.76 (11)	C8—C9—H9	125.9
C7—Fe1—C3	102.82 (11)	C10—C9—H9	125.9
C2—Fe1—C8	103.64 (11)	Fe1—C9—H9	126.5
C7—Fe1—C8	40.69 (11)	C9—C10—C6	108.6 (2)
C3—Fe1—C8	115.78 (11)	C9—C10—Fe1	69.92 (15)
C2—Fe1—C10	156.57 (11)	C6—C10—Fe1	69.66 (14)
C7—Fe1—C10	68.55 (10)	C9—C10—H10	125.7
C3—Fe1—C10	162.68 (11)	C6—C10—H10	125.7
C8—Fe1—C10	68.11 (11)	Fe1—C10—H10	126.3
C2—Fe1—C6	158.63 (10)	C13—C11—C12	109.4 (2)
C7—Fe1—C6	41.21 (9)	C13—C11—C14	107.3 (2)
C3—Fe1—C6	122.96 (11)	C12—C11—C14	109.5 (2)
C8—Fe1—C6	68.87 (10)	C13—C11—P1	109.40 (18)
C10—Fe1—C6	40.87 (10)	C12—C11—P1	113.85 (18)
C2—Fe1—C9	119.19 (11)	C14—C11—P1	107.18 (17)
C7—Fe1—C9	68.28 (11)	C11—C12—H12A	109.5
C3—Fe1—C9	151.85 (11)	C11—C12—H12B	109.5
C8—Fe1—C9	40.25 (12)	H12A—C12—H12B	109.5
C10—Fe1—C9	40.57 (10)	C11—C12—H12C	109.5
C6—Fe1—C9	68.74 (11)	H12A—C12—H12C	109.5
C2—Fe1—C4	68.35 (11)	H12B—C12—H12C	109.5
C7—Fe1—C4	118.10 (11)	C11—C13—H13A	109.5
C3—Fe1—C4	40.36 (10)	C11—C13—H13B	109.5
C8—Fe1—C4	151.42 (12)	H13A—C13—H13B	109.5
C10—Fe1—C4	129.25 (10)	C11—C13—H13C	109.5
C6—Fe1—C4	108.16 (10)	H13A—C13—H13C	109.5
C9—Fe1—C4	167.31 (11)	H13B—C13—H13C	109.5
C2—Fe1—C1	41.22 (9)	C11—C14—H14A	109.5
C7—Fe1—C1	159.11 (10)	C11—C14—H14B	109.5
C3—Fe1—C1	68.98 (10)	H14A—C14—H14B	109.5
C8—Fe1—C1	124.12 (10)	C11—C14—H14C	109.5
C10—Fe1—C1	124.18 (10)	H14A—C14—H14C	109.5
C6—Fe1—C1	159.08 (9)	H14B—C14—H14C	109.5
C9—Fe1—C1	109.44 (10)	C17—C15—C16	108.4 (2)
C4—Fe1—C1	68.77 (10)	C17—C15—C18	109.9 (2)
C2—Fe1—C5	68.49 (10)	C16—C15—C18	107.9 (2)
C7—Fe1—C5	155.44 (11)	C17—C15—P1	112.14 (17)
C3—Fe1—C5	68.09 (10)	C16—C15—P1	107.13 (17)
C8—Fe1—C5	163.88 (11)	C18—C15—P1	111.21 (19)
C10—Fe1—C5	113.26 (10)	C15—C16—H16A	109.5
C6—Fe1—C5	123.45 (10)	C15—C16—H16B	109.5
C9—Fe1—C5	130.18 (11)	H16A—C16—H16B	109.5
C4—Fe1—C5	40.44 (10)	C15—C16—H16C	109.5
C1—Fe1—C5	40.88 (9)	H16A—C16—H16C	109.5
C1—P1—C11	108.48 (11)	H16B—C16—H16C	109.5
C1—P1—C15	101.83 (11)	C15—C17—H17A	109.5
C11—P1—C15	111.84 (11)	C15—C17—H17B	109.5
C1—P1—S1	111.75 (8)	H17A—C17—H17B	109.5
C11—P1—S1	110.08 (9)	C15—C17—H17C	109.5
C15—P1—S1	112.57 (9)	H17A—C17—H17C	109.5
C6—P2—C23	102.25 (11)	H17B—C17—H17C	109.5
C6—P2—C19	109.61 (12)	C15—C18—H18A	109.5
C23—P2—C19	110.88 (11)	C15—C18—H18B	109.5
C6—P2—S2	111.11 (9)	H18A—C18—H18B	109.5
C23—P2—S2	111.07 (9)	C15—C18—H18C	109.5
C19—P2—S2	111.56 (9)	H18A—C18—H18C	109.5
C5—C1—C2	106.3 (2)	H18B—C18—H18C	109.5
C5—C1—P1	131.12 (18)	C22—C19—C20	109.2 (2)
C2—C1—P1	121.63 (18)	C22—C19—C21	109.3 (2)
C5—C1—Fe1	69.59 (13)	C20—C19—C21	107.2 (2)
C2—C1—Fe1	68.43 (13)	C22—C19—P2	114.53 (18)
P1—C1—Fe1	135.08 (13)	C20—C19—P2	109.48 (18)
C3—C2—C1	108.6 (2)	C21—C19—P2	106.88 (17)
C3—C2—Fe1	69.94 (15)	C19—C20—H20A	109.5
C1—C2—Fe1	70.35 (13)	C19—C20—H20B	109.5
C3—C2—H2	125.7	H20A—C20—H20B	109.5
C1—C2—H2	125.7	C19—C20—H20C	109.5
Fe1—C2—H2	125.6	H20A—C20—H20C	109.5
C4—C3—C2	108.4 (2)	H20B—C20—H20C	109.5
C4—C3—Fe1	70.46 (15)	C19—C21—H21A	109.5
C2—C3—Fe1	69.31 (15)	C19—C21—H21B	109.5
C4—C3—H3	125.8	H21A—C21—H21B	109.5
C2—C3—H3	125.8	C19—C21—H21C	109.5
Fe1—C3—H3	126.0	H21A—C21—H21C	109.5
C3—C4—C5	108.0 (2)	H21B—C21—H21C	109.5
C3—C4—Fe1	69.19 (15)	C19—C22—H22A	109.5
C5—C4—Fe1	69.85 (14)	C19—C22—H22B	109.5
C3—C4—H4	126.0	H22A—C22—H22B	109.5
C5—C4—H4	126.0	C19—C22—H22C	109.5
Fe1—C4—H4	126.6	H22A—C22—H22C	109.5
C4—C5—C1	108.7 (2)	H22B—C22—H22C	109.5
C4—C5—Fe1	69.72 (14)	C25—C23—C26	108.2 (2)
C1—C5—Fe1	69.53 (13)	C25—C23—C24	108.1 (2)
C4—C5—H5	125.7	C26—C23—C24	110.2 (2)
C1—C5—H5	125.7	C25—C23—P2	107.68 (17)
Fe1—C5—H5	126.7	C26—C23—P2	110.38 (17)
C10—C6—C7	106.5 (2)	C24—C23—P2	112.16 (17)
C10—C6—P2	131.91 (19)	C23—C24—H24A	109.5
C7—C6—P2	120.9 (2)	C23—C24—H24B	109.5
C10—C6—Fe1	69.48 (14)	H24A—C24—H24B	109.5
C7—C6—Fe1	68.69 (13)	C23—C24—H24C	109.5
P2—C6—Fe1	133.57 (14)	H24A—C24—H24C	109.5
C8—C7—C6	108.5 (2)	H24B—C24—H24C	109.5
C8—C7—Fe1	70.25 (15)	C23—C25—H25A	109.5
C6—C7—Fe1	70.09 (13)	C23—C25—H25B	109.5
C8—C7—H7	125.7	H25A—C25—H25B	109.5
C6—C7—H7	125.7	C23—C25—H25C	109.5
Fe1—C7—H7	125.5	H25A—C25—H25C	109.5
C9—C8—C7	108.3 (2)	H25B—C25—H25C	109.5
C9—C8—Fe1	70.11 (15)	C23—C26—H26A	109.5
C7—C8—Fe1	69.07 (14)	C23—C26—H26B	109.5
C9—C8—H8	125.9	H26A—C26—H26B	109.5
C7—C8—H8	125.9	C23—C26—H26C	109.5
Fe1—C8—H8	126.5	H26A—C26—H26C	109.5
C8—C9—C10	108.1 (2)	H26B—C26—H26C	109.5
C8—C9—Fe1	69.64 (16)

C11—P1—C1—C5	−25.0 (3)	Fe1—C8—C9—C10	−59.06 (18)
C15—P1—C1—C5	93.1 (2)	C7—C8—C9—Fe1	58.69 (18)
S1—P1—C1—C5	−146.5 (2)	C8—C9—C10—C6	0.0 (3)
C11—P1—C1—C2	168.08 (19)	Fe1—C9—C10—C6	−59.09 (17)
C15—P1—C1—C2	−73.8 (2)	C8—C9—C10—Fe1	59.14 (18)
S1—P1—C1—C2	46.5 (2)	C7—C6—C10—C9	0.3 (3)
C11—P1—C1—Fe1	77.7 (2)	P2—C6—C10—C9	−170.0 (2)
C15—P1—C1—Fe1	−164.18 (17)	Fe1—C6—C10—C9	59.26 (17)
S1—P1—C1—Fe1	−43.80 (19)	C7—C6—C10—Fe1	−58.97 (16)
C5—C1—C2—C3	−0.1 (3)	P2—C6—C10—Fe1	130.8 (2)
P1—C1—C2—C3	169.70 (18)	C1—P1—C11—C13	−170.78 (18)
Fe1—C1—C2—C3	−59.71 (17)	C15—P1—C11—C13	77.7 (2)
C5—C1—C2—Fe1	59.60 (16)	S1—P1—C11—C13	−48.2 (2)
P1—C1—C2—Fe1	−130.60 (18)	C1—P1—C11—C12	66.5 (2)
C1—C2—C3—C4	0.1 (3)	C15—P1—C11—C12	−45.0 (2)
Fe1—C2—C3—C4	−59.82 (18)	S1—P1—C11—C12	−170.93 (16)
C1—C2—C3—Fe1	59.96 (17)	C1—P1—C11—C14	−54.8 (2)
C2—C3—C4—C5	−0.1 (3)	C15—P1—C11—C14	−166.27 (17)
Fe1—C3—C4—C5	−59.24 (17)	S1—P1—C11—C14	67.80 (18)
C2—C3—C4—Fe1	59.11 (18)	C1—P1—C15—C17	−43.9 (2)
C3—C4—C5—C1	0.1 (3)	C11—P1—C15—C17	71.8 (2)
Fe1—C4—C5—C1	−58.76 (17)	S1—P1—C15—C17	−163.66 (16)
C3—C4—C5—Fe1	58.83 (17)	C1—P1—C15—C16	74.9 (2)
C2—C1—C5—C4	0.0 (3)	C11—P1—C15—C16	−169.44 (18)
P1—C1—C5—C4	−168.43 (19)	S1—P1—C15—C16	−44.9 (2)
Fe1—C1—C5—C4	58.88 (17)	C1—P1—C15—C18	−167.36 (19)
C2—C1—C5—Fe1	−58.85 (16)	C11—P1—C15—C18	−51.7 (2)
P1—C1—C5—Fe1	132.7 (2)	S1—P1—C15—C18	72.8 (2)
C23—P2—C6—C10	94.4 (2)	C6—P2—C19—C22	67.3 (2)
C19—P2—C6—C10	−23.3 (3)	C23—P2—C19—C22	−44.9 (2)
S2—P2—C6—C10	−147.1 (2)	S2—P2—C19—C22	−169.21 (17)
C23—P2—C6—C7	−74.7 (2)	C6—P2—C19—C20	−169.67 (18)
C19—P2—C6—C7	167.59 (19)	C23—P2—C19—C20	78.2 (2)
S2—P2—C6—C7	43.8 (2)	S2—P2—C19—C20	−46.2 (2)
C23—P2—C6—Fe1	−163.87 (17)	C6—P2—C19—C21	−53.9 (2)
C19—P2—C6—Fe1	78.5 (2)	C23—P2—C19—C21	−166.08 (18)
S2—P2—C6—Fe1	−45.31 (19)	S2—P2—C19—C21	69.56 (19)
C10—C6—C7—C8	−0.5 (3)	C6—P2—C23—C25	76.8 (2)
P2—C6—C7—C8	171.06 (18)	C19—P2—C23—C25	−166.41 (18)
Fe1—C6—C7—C8	−59.98 (18)	S2—P2—C23—C25	−41.8 (2)
C10—C6—C7—Fe1	59.47 (16)	C6—P2—C23—C26	−165.29 (19)
P2—C6—C7—Fe1	−128.96 (18)	C19—P2—C23—C26	−48.5 (2)
C6—C7—C8—C9	0.5 (3)	S2—P2—C23—C26	76.11 (19)
Fe1—C7—C8—C9	−59.34 (18)	C6—P2—C23—C24	−42.0 (2)
C6—C7—C8—Fe1	59.89 (17)	C19—P2—C23—C24	74.8 (2)
C7—C8—C9—C10	−0.4 (3)	S2—P2—C23—C24	−160.55 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12C···S1ⁱ	0.98	2.83	3.650 (3)	141
C13—H13C···S1	0.98	2.86	3.353 (3)	112
C14—H14A···S1	0.98	2.99	3.533 (3)	116
C16—H16C···S1	0.98	2.86	3.351 (3)	112
C20—H20C···S2	0.98	2.83	3.383 (3)	117
C25—H25C···S2	0.98	2.78	3.284 (3)	113

Symmetry code: (i) −x, y−1/2, −z+1/2.

[1,1'-Bis(dicyclohexylphosphanyl)ferrocene-\ κ²P,P'][chlorido/cyanido(0.25/1.75)]zinc(II) (Complex-4) top

Crystal data top

[Zn(CN)_1.75Cl_0.25{(C₁₇H₂₆P)₂Fe}]	F(000) = 738
M_r = 698.31	D_x = 1.408 Mg m⁻³
Monoclinic, P2₁/m	Mo Kα radiation, λ = 0.71073 Å
a = 8.2992 (6) Å	Cell parameters from 4968 reflections
b = 21.6504 (18) Å	θ = 2.7–27.2°
c = 9.9175 (7) Å	µ = 1.31 mm⁻¹
β = 112.451 (4)°	T = 100 K
V = 1646.9 (2) Å³	Block, yellow
Z = 2	0.31 × 0.19 × 0.17 mm

Data collection top

Bruker SMART APEX CCD area detector diffractometer	3872 independent reflections
Radiation source: sealed tube	3047 reflections with I > 2σ(I)
Detector resolution: 8 pixels mm^-1	R_int = 0.042
ω and φ scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −10→10
T_min = 0.633, T_max = 0.694	k = −28→27
16559 measured reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0359P)² + 2.1228P] where P = (F_o² + 2F_c²)/3
3872 reflections	(Δ/σ)_max = 0.001
216 parameters	Δρ_max = 1.29 e Å⁻³
41 restraints	Δρ_min = −1.21 e Å⁻³

Special details top

Refinement. All H atoms were positioned geometrically and refined using a riding model with C—H = 0.95–0.99 Å and with U_iso(H) = 1.2 (1.5 for methyl groups) times U_eq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Fe1	0.39104 (6)	0.750000	0.04304 (6)	0.01089 (13)
P1	0.70108 (8)	0.66274 (3)	0.31225 (7)	0.01124 (15)
C1	0.5083 (3)	0.67093 (11)	0.1489 (3)	0.0125 (5)
C2	0.3282 (3)	0.67279 (12)	0.1311 (3)	0.0146 (5)
H2	0.285201	0.671795	0.207193	0.018*
C3	0.2263 (3)	0.67638 (12)	−0.0203 (3)	0.0181 (6)
H3	0.102617	0.677907	−0.063055	0.022*
C4	0.3388 (3)	0.67731 (12)	−0.0976 (3)	0.0167 (6)
H4	0.303809	0.679494	−0.200506	0.020*
C5	0.5136 (3)	0.67441 (11)	0.0063 (3)	0.0139 (5)
H5	0.615762	0.674721	−0.015179	0.017*
C6	0.6218 (3)	0.65205 (12)	0.4605 (3)	0.0135 (5)
H6	0.542889	0.687635	0.455587	0.016*
C7	0.7734 (3)	0.65530 (13)	0.6103 (3)	0.0175 (6)
H7A	0.856111	0.621160	0.618995	0.021*
H7B	0.836611	0.694804	0.618972	0.021*
C8	0.7055 (4)	0.65047 (13)	0.7338 (3)	0.0196 (6)
H8A	0.805571	0.650217	0.828858	0.023*
H8B	0.633155	0.687131	0.731394	0.023*
C9	0.5976 (4)	0.59229 (13)	0.7204 (3)	0.0175 (6)
H9A	0.672433	0.555450	0.732157	0.021*
H9B	0.551282	0.591661	0.798775	0.021*
C10	0.4471 (3)	0.59007 (13)	0.5725 (3)	0.0163 (6)
H10A	0.367636	0.625286	0.563574	0.020*
H10B	0.380329	0.551398	0.564018	0.020*
C11	0.5157 (3)	0.59303 (12)	0.4500 (3)	0.0150 (5)
H11A	0.416421	0.591905	0.354546	0.018*
H11B	0.590066	0.556553	0.455921	0.018*
C12	0.8005 (4)	0.58702 (15)	0.2966 (3)	0.0102 (7)	0.859 (2)
H12	0.849064	0.568305	0.396261	0.012*	0.859 (2)
C13	0.6726 (5)	0.54029 (17)	0.1954 (4)	0.0110 (10)	0.859 (2)
H13A	0.577988	0.532113	0.230642	0.013*	0.859 (2)
H13B	0.619481	0.557918	0.095971	0.013*	0.859 (2)
C14	0.7636 (4)	0.47984 (14)	0.1895 (4)	0.0151 (7)	0.859 (2)
H14A	0.678514	0.451016	0.121409	0.018*	0.859 (2)
H14B	0.809135	0.460602	0.287471	0.018*	0.859 (2)
C15	0.9144 (4)	0.49073 (14)	0.1389 (4)	0.0152 (7)	0.859 (2)
H15A	0.974303	0.451125	0.139615	0.018*	0.859 (2)
H15B	0.867973	0.506778	0.037785	0.018*	0.859 (2)
C16	1.0433 (4)	0.53661 (15)	0.2386 (4)	0.0186 (7)	0.859 (2)
H16A	1.136346	0.544745	0.201428	0.022*	0.859 (2)
H16B	1.098398	0.518535	0.337403	0.022*	0.859 (2)
C17	0.9550 (4)	0.59756 (14)	0.2482 (4)	0.0152 (6)	0.859 (2)
H17A	0.912157	0.618114	0.151764	0.018*	0.859 (2)
H17B	1.041386	0.625206	0.318968	0.018*	0.859 (2)
C12'	0.791 (3)	0.5956 (10)	0.251 (2)	0.0102 (7)	0.141 (2)
H12'	0.833910	0.614022	0.178466	0.012*	0.141 (2)
C13'	0.666 (3)	0.5455 (12)	0.163 (3)	0.0110 (10)	0.141 (2)
H13C	0.608519	0.526880	0.223987	0.013*	0.141 (2)
H13D	0.575006	0.564757	0.077348	0.013*	0.141 (2)
C14'	0.754 (2)	0.4948 (8)	0.111 (2)	0.0151 (7)	0.141 (2)
H14C	0.677899	0.458010	0.088426	0.018*	0.141 (2)
H14D	0.762212	0.508587	0.018433	0.018*	0.141 (2)
C15'	0.929 (2)	0.4757 (8)	0.210 (2)	0.0152 (7)	0.141 (2)
H15C	0.987158	0.454552	0.152524	0.018*	0.141 (2)
H15D	0.916608	0.445203	0.279984	0.018*	0.141 (2)
C16'	1.048 (2)	0.5270 (9)	0.297 (2)	0.0186 (7)	0.141 (2)
H16C	1.088105	0.551218	0.230998	0.022*	0.141 (2)
H16D	1.151497	0.508553	0.373525	0.022*	0.141 (2)
C17'	0.957 (2)	0.5704 (8)	0.3681 (19)	0.0152 (6)	0.141 (2)
H17C	0.928751	0.547723	0.442733	0.018*	0.141 (2)
H17D	1.036393	0.604965	0.416832	0.018*	0.141 (2)
Zn1	0.8872 (3)	0.750000	0.3270 (2)	0.01273 (12)	0.859 (2)
N1	1.2684 (5)	0.750000	0.5621 (4)	0.0246 (7)	0.859 (2)
N2	0.9075 (5)	0.750000	0.0182 (4)	0.0194 (7)	0.859 (2)
C18	1.1216 (9)	0.750000	0.4819 (7)	0.0246 (7)	0.859 (2)
C19	0.9107 (17)	0.750000	0.1281 (10)	0.0194 (7)	0.859 (2)
Zn1'	0.8881 (17)	0.750000	0.3293 (13)	0.01273 (12)	0.141 (2)
Cl1	1.1538 (18)	0.750000	0.5160 (11)	0.0246 (7)	0.141 (2)
Cl2	0.916 (2)	0.750000	0.1084 (17)	0.0194 (7)	0.141 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0125 (3)	0.0081 (3)	0.0121 (3)	0.000	0.0048 (2)	0.000
P1	0.0122 (3)	0.0088 (3)	0.0131 (3)	0.0001 (3)	0.0052 (3)	−0.0005 (3)
C1	0.0138 (12)	0.0080 (12)	0.0152 (13)	−0.0027 (10)	0.0048 (11)	0.0006 (10)
C2	0.0144 (12)	0.0103 (13)	0.0204 (14)	−0.0006 (10)	0.0080 (11)	0.0029 (11)
C3	0.0142 (13)	0.0112 (13)	0.0226 (15)	−0.0019 (10)	0.0001 (12)	−0.0014 (11)
C4	0.0231 (14)	0.0087 (12)	0.0154 (13)	−0.0011 (11)	0.0042 (12)	−0.0051 (10)
C5	0.0185 (13)	0.0098 (13)	0.0145 (13)	0.0028 (10)	0.0077 (11)	−0.0011 (10)
C6	0.0162 (12)	0.0120 (13)	0.0131 (13)	−0.0001 (10)	0.0065 (11)	−0.0008 (10)
C7	0.0174 (13)	0.0197 (14)	0.0143 (14)	−0.0050 (11)	0.0047 (11)	−0.0026 (11)
C8	0.0220 (14)	0.0219 (15)	0.0147 (14)	−0.0043 (12)	0.0069 (12)	−0.0034 (11)
C9	0.0230 (14)	0.0180 (14)	0.0150 (13)	0.0020 (11)	0.0110 (12)	0.0005 (11)
C10	0.0205 (14)	0.0139 (13)	0.0175 (14)	−0.0035 (11)	0.0107 (12)	0.0000 (11)
C11	0.0189 (13)	0.0124 (13)	0.0133 (13)	−0.0018 (11)	0.0058 (11)	−0.0007 (10)
C12	0.0130 (13)	0.0076 (15)	0.0086 (18)	0.0024 (11)	0.0025 (15)	0.0019 (13)
C13	0.0128 (13)	0.0092 (14)	0.012 (2)	0.0009 (10)	0.0051 (14)	0.0023 (15)
C14	0.0198 (15)	0.0095 (15)	0.0186 (17)	−0.0001 (12)	0.0101 (14)	−0.0009 (13)
C15	0.0183 (15)	0.0112 (16)	0.0191 (18)	0.0020 (12)	0.0103 (14)	0.0001 (13)
C16	0.0167 (14)	0.0143 (16)	0.027 (2)	0.0020 (12)	0.0109 (16)	−0.0026 (15)
C17	0.0120 (14)	0.0100 (15)	0.0239 (17)	−0.0010 (11)	0.0071 (13)	−0.0052 (12)
C12'	0.0130 (13)	0.0076 (15)	0.0086 (18)	0.0024 (11)	0.0025 (15)	0.0019 (13)
C13'	0.0128 (13)	0.0092 (14)	0.012 (2)	0.0009 (10)	0.0051 (14)	0.0023 (15)
C14'	0.0198 (15)	0.0095 (15)	0.0186 (17)	−0.0001 (12)	0.0101 (14)	−0.0009 (13)
C15'	0.0183 (15)	0.0112 (16)	0.0191 (18)	0.0020 (12)	0.0103 (14)	0.0001 (13)
C16'	0.0167 (14)	0.0143 (16)	0.027 (2)	0.0020 (12)	0.0109 (16)	−0.0026 (15)
C17'	0.0120 (14)	0.0100 (15)	0.0239 (17)	−0.0010 (11)	0.0071 (13)	−0.0052 (12)
Zn1	0.0127 (2)	0.0110 (2)	0.0143 (2)	0.000	0.00506 (18)	0.000
N1	0.019 (2)	0.0221 (13)	0.024 (2)	0.000	−0.0015 (16)	0.000
N2	0.0134 (11)	0.0188 (11)	0.024 (2)	0.000	0.0042 (15)	0.000
C18	0.019 (2)	0.0221 (13)	0.024 (2)	0.000	−0.0015 (16)	0.000
C19	0.0134 (11)	0.0188 (11)	0.024 (2)	0.000	0.0042 (15)	0.000
Zn1'	0.0127 (2)	0.0110 (2)	0.0143 (2)	0.000	0.00506 (18)	0.000
Cl1	0.019 (2)	0.0221 (13)	0.024 (2)	0.000	−0.0015 (16)	0.000
Cl2	0.0134 (11)	0.0188 (11)	0.024 (2)	0.000	0.0042 (15)	0.000

Geometric parameters (Å, º) top

Fe1—C5	2.032 (2)	C11—H11B	0.9900
Fe1—C5ⁱ	2.032 (2)	C12—C13	1.531 (4)
Fe1—C4ⁱ	2.036 (3)	C12—C17	1.548 (4)
Fe1—C4	2.036 (3)	C12—H12	1.0000
Fe1—C3	2.037 (3)	C13—C14	1.523 (4)
Fe1—C3ⁱ	2.037 (3)	C13—H13A	0.9900
Fe1—C2	2.044 (3)	C13—H13B	0.9900
Fe1—C2ⁱ	2.044 (3)	C14—C15	1.533 (4)
Fe1—C1	2.049 (3)	C14—H14A	0.9900
Fe1—C1ⁱ	2.049 (3)	C14—H14B	0.9900
P1—C1	1.799 (3)	C15—C16	1.517 (4)
P1—C12'	1.84 (2)	C15—H15A	0.9900
P1—C6	1.841 (3)	C15—H15B	0.9900
P1—C12	1.868 (3)	C16—C17	1.530 (4)
P1—Zn1	2.4089 (16)	C16—H16A	0.9900
P1—Zn1'	2.410 (9)	C16—H16B	0.9900
C1—C5	1.434 (4)	C17—H17A	0.9900
C1—C2	1.437 (3)	C17—H17B	0.9900
C2—C3	1.416 (4)	C12'—C13'	1.522 (17)
C2—H2	0.9500	C12'—C17'	1.526 (16)
C3—C4	1.416 (4)	C12'—H12'	1.0000
C3—H3	0.9500	C13'—C14'	1.514 (17)
C4—C5	1.424 (4)	C13'—H13C	0.9900
C4—H4	0.9500	C13'—H13D	0.9900
C5—H5	0.9500	C14'—C15'	1.469 (16)
C6—C11	1.532 (4)	C14'—H14C	0.9900
C6—C7	1.539 (4)	C14'—H14D	0.9900
C6—H6	1.0000	C15'—C16'	1.512 (16)
C7—C8	1.534 (4)	C15'—H15C	0.9900
C7—H7A	0.9900	C15'—H15D	0.9900
C7—H7B	0.9900	C16'—C17'	1.534 (16)
C8—C9	1.522 (4)	C16'—H16C	0.9900
C8—H8A	0.9900	C16'—H16D	0.9900
C8—H8B	0.9900	C17'—H17C	0.9900
C9—C10	1.522 (4)	C17'—H17D	0.9900
C9—H9A	0.9900	Zn1—C18	1.965 (6)
C9—H9B	0.9900	Zn1—C19	2.055 (6)
C10—C11	1.527 (3)	N1—C18	1.174 (7)
C10—H10A	0.9900	N2—C19	1.081 (8)
C10—H10B	0.9900	Zn1'—Cl1	2.274 (13)
C11—H11A	0.9900	Zn1'—Cl2	2.288 (13)

C5—Fe1—C5ⁱ	107.31 (15)	H8A—C8—H8B	107.9
C5—Fe1—C4ⁱ	119.33 (11)	C10—C9—C8	110.4 (2)
C5ⁱ—Fe1—C4ⁱ	40.98 (10)	C10—C9—H9A	109.6
C5—Fe1—C4	40.98 (10)	C8—C9—H9A	109.6
C5ⁱ—Fe1—C4	119.33 (11)	C10—C9—H9B	109.6
C4ⁱ—Fe1—C4	101.21 (16)	C8—C9—H9B	109.6
C5—Fe1—C3	68.73 (11)	H9A—C9—H9B	108.1
C5ⁱ—Fe1—C3	153.90 (11)	C9—C10—C11	110.4 (2)
C4ⁱ—Fe1—C3	116.83 (11)	C9—C10—H10A	109.6
C4—Fe1—C3	40.69 (11)	C11—C10—H10A	109.6
C5—Fe1—C3ⁱ	153.90 (11)	C9—C10—H10B	109.6
C5ⁱ—Fe1—C3ⁱ	68.73 (11)	C11—C10—H10B	109.6
C4ⁱ—Fe1—C3ⁱ	40.69 (11)	H10A—C10—H10B	108.1
C4—Fe1—C3ⁱ	116.83 (11)	C10—C11—C6	111.1 (2)
C3—Fe1—C3ⁱ	103.00 (15)	C10—C11—H11A	109.4
C5—Fe1—C2	69.20 (10)	C6—C11—H11A	109.4
C5ⁱ—Fe1—C2	164.22 (11)	C10—C11—H11B	109.4
C4ⁱ—Fe1—C2	154.46 (11)	C6—C11—H11B	109.4
C4—Fe1—C2	68.79 (11)	H11A—C11—H11B	108.0
C3—Fe1—C2	40.61 (11)	C13—C12—C17	110.1 (3)
C3ⁱ—Fe1—C2	121.40 (11)	C13—C12—P1	114.6 (2)
C5—Fe1—C2ⁱ	164.22 (11)	C17—C12—P1	109.9 (2)
C5ⁱ—Fe1—C2ⁱ	69.20 (10)	C13—C12—H12	107.3
C4ⁱ—Fe1—C2ⁱ	68.79 (11)	C17—C12—H12	107.3
C4—Fe1—C2ⁱ	154.46 (11)	P1—C12—H12	107.3
C3—Fe1—C2ⁱ	121.40 (11)	C14—C13—C12	111.3 (3)
C3ⁱ—Fe1—C2ⁱ	40.61 (11)	C14—C13—H13A	109.4
C2—Fe1—C2ⁱ	109.74 (15)	C12—C13—H13A	109.4
C5—Fe1—C1	41.14 (10)	C14—C13—H13B	109.4
C5ⁱ—Fe1—C1	126.34 (10)	C12—C13—H13B	109.4
C4ⁱ—Fe1—C1	158.70 (11)	H13A—C13—H13B	108.0
C4—Fe1—C1	68.94 (10)	C13—C14—C15	111.0 (3)
C3—Fe1—C1	68.63 (10)	C13—C14—H14A	109.4
C3ⁱ—Fe1—C1	160.59 (11)	C15—C14—H14A	109.4
C2—Fe1—C1	41.11 (10)	C13—C14—H14B	109.4
C2ⁱ—Fe1—C1	127.80 (11)	C15—C14—H14B	109.4
C5—Fe1—C1ⁱ	126.34 (10)	H14A—C14—H14B	108.0
C5ⁱ—Fe1—C1ⁱ	41.14 (10)	C16—C15—C14	110.4 (3)
C4ⁱ—Fe1—C1ⁱ	68.94 (10)	C16—C15—H15A	109.6
C4—Fe1—C1ⁱ	158.70 (11)	C14—C15—H15A	109.6
C3—Fe1—C1ⁱ	160.59 (11)	C16—C15—H15B	109.6
C3ⁱ—Fe1—C1ⁱ	68.64 (10)	C14—C15—H15B	109.6
C2—Fe1—C1ⁱ	127.80 (11)	H15A—C15—H15B	108.1
C2ⁱ—Fe1—C1ⁱ	41.11 (10)	C15—C16—C17	111.7 (3)
C1—Fe1—C1ⁱ	113.30 (14)	C15—C16—H16A	109.3
C1—P1—C12'	96.6 (6)	C17—C16—H16A	109.3
C1—P1—C6	105.39 (12)	C15—C16—H16B	109.3
C12'—P1—C6	118.6 (8)	C17—C16—H16B	109.3
C1—P1—C12	106.30 (13)	H16A—C16—H16B	107.9
C6—P1—C12	105.08 (13)	C16—C17—C12	111.4 (2)
C1—P1—Zn1	107.85 (9)	C16—C17—H17A	109.3
C6—P1—Zn1	117.83 (10)	C12—C17—H17A	109.3
C12—P1—Zn1	113.57 (12)	C16—C17—H17B	109.3
C1—P1—Zn1'	108.3 (3)	C12—C17—H17B	109.3
C12'—P1—Zn1'	108.1 (8)	H17A—C17—H17B	108.0
C6—P1—Zn1'	117.4 (3)	C13'—C12'—C17'	113.7 (16)
C5—C1—C2	107.4 (2)	C13'—C12'—P1	118.7 (14)
C5—C1—P1	122.80 (19)	C17'—C12'—P1	113.2 (13)
C2—C1—P1	129.7 (2)	C13'—C12'—H12'	102.9
C5—C1—Fe1	68.77 (14)	C17'—C12'—H12'	102.9
C2—C1—Fe1	69.24 (14)	P1—C12'—H12'	102.9
P1—C1—Fe1	128.96 (13)	C14'—C13'—C12'	113.7 (17)
C3—C2—C1	107.7 (2)	C14'—C13'—H13C	108.8
C3—C2—Fe1	69.42 (15)	C12'—C13'—H13C	108.8
C1—C2—Fe1	69.65 (14)	C14'—C13'—H13D	108.8
C3—C2—H2	126.2	C12'—C13'—H13D	108.8
C1—C2—H2	126.2	H13C—C13'—H13D	107.7
Fe1—C2—H2	126.3	C15'—C14'—C13'	117.1 (15)
C4—C3—C2	108.9 (2)	C15'—C14'—H14C	108.0
C4—C3—Fe1	69.64 (15)	C13'—C14'—H14C	108.0
C2—C3—Fe1	69.97 (15)	C15'—C14'—H14D	108.0
C4—C3—H3	125.5	C13'—C14'—H14D	108.0
C2—C3—H3	125.5	H14C—C14'—H14D	107.3
Fe1—C3—H3	126.4	C14'—C15'—C16'	115.8 (14)
C3—C4—C5	107.9 (2)	C14'—C15'—H15C	108.3
C3—C4—Fe1	69.66 (15)	C16'—C15'—H15C	108.3
C5—C4—Fe1	69.34 (14)	C14'—C15'—H15D	108.3
C3—C4—H4	126.0	C16'—C15'—H15D	108.3
C5—C4—H4	126.0	H15C—C15'—H15D	107.4
Fe1—C4—H4	126.5	C15'—C16'—C17'	112.7 (14)
C4—C5—C1	108.0 (2)	C15'—C16'—H16C	109.1
C4—C5—Fe1	69.68 (14)	C17'—C16'—H16C	109.1
C1—C5—Fe1	70.09 (14)	C15'—C16'—H16D	109.1
C4—C5—H5	126.0	C17'—C16'—H16D	109.1
C1—C5—H5	126.0	H16C—C16'—H16D	107.8
Fe1—C5—H5	125.8	C12'—C17'—C16'	109.1 (15)
C11—C6—C7	109.9 (2)	C12'—C17'—H17C	109.9
C11—C6—P1	114.93 (18)	C16'—C17'—H17C	109.9
C7—C6—P1	110.83 (17)	C12'—C17'—H17D	109.9
C11—C6—H6	106.9	C16'—C17'—H17D	109.9
C7—C6—H6	106.9	H17C—C17'—H17D	108.3
P1—C6—H6	106.9	C18—Zn1—C19	108.8 (5)
C8—C7—C6	110.7 (2)	C18—Zn1—P1	117.88 (15)
C8—C7—H7A	109.5	C19—Zn1—P1	103.6 (2)
C6—C7—H7A	109.5	C18—Zn1—P1ⁱ	117.88 (15)
C8—C7—H7B	109.5	C19—Zn1—P1ⁱ	103.6 (2)
C6—C7—H7B	109.5	P1—Zn1—P1ⁱ	103.30 (9)
H7A—C7—H7B	108.1	N1—C18—Zn1	172.6 (8)
C9—C8—C7	111.7 (2)	N2—C19—Zn1	173.7 (11)
C9—C8—H8A	109.3	Cl1—Zn1'—Cl2	111.1 (9)
C7—C8—H8A	109.3	Cl1—Zn1'—P1	117.1 (4)
C9—C8—H8B	109.3	Cl2—Zn1'—P1	103.3 (4)
C7—C8—H8B	109.3	P1—Zn1'—P1ⁱ	103.2 (5)

C12'—P1—C1—C5	−51.9 (8)	C12'—P1—C6—C7	83.0 (7)
C6—P1—C1—C5	−174.0 (2)	C12—P1—C6—C7	77.4 (2)
C12—P1—C1—C5	−62.8 (2)	Zn1—P1—C6—C7	−50.2 (2)
Zn1—P1—C1—C5	59.3 (2)	Zn1'—P1—C6—C7	−49.9 (3)
Zn1'—P1—C1—C5	59.6 (4)	C11—C6—C7—C8	−55.4 (3)
C12'—P1—C1—C2	125.4 (8)	P1—C6—C7—C8	176.42 (18)
C6—P1—C1—C2	3.3 (3)	C6—C7—C8—C9	55.7 (3)
C12—P1—C1—C2	114.5 (2)	C7—C8—C9—C10	−56.5 (3)
Zn1—P1—C1—C2	−123.3 (2)	C8—C9—C10—C11	57.5 (3)
Zn1'—P1—C1—C2	−123.0 (4)	C9—C10—C11—C6	−58.6 (3)
C12'—P1—C1—Fe1	−140.1 (8)	C7—C6—C11—C10	57.4 (3)
C6—P1—C1—Fe1	97.89 (18)	P1—C6—C11—C10	−176.77 (18)
C12—P1—C1—Fe1	−150.90 (17)	C1—P1—C12—C13	−23.9 (3)
Zn1—P1—C1—Fe1	−28.78 (19)	C6—P1—C12—C13	87.5 (2)
Zn1'—P1—C1—Fe1	−28.5 (4)	Zn1—P1—C12—C13	−142.3 (2)
C5—C1—C2—C3	0.9 (3)	C1—P1—C12—C17	100.7 (2)
P1—C1—C2—C3	−176.8 (2)	C6—P1—C12—C17	−147.8 (2)
Fe1—C1—C2—C3	59.22 (18)	Zn1—P1—C12—C17	−17.7 (2)
C5—C1—C2—Fe1	−58.35 (17)	C17—C12—C13—C14	55.8 (3)
P1—C1—C2—Fe1	124.0 (2)	P1—C12—C13—C14	−179.6 (2)
C1—C2—C3—C4	−0.5 (3)	C12—C13—C14—C15	−57.6 (4)
Fe1—C2—C3—C4	58.89 (18)	C13—C14—C15—C16	57.1 (4)
C1—C2—C3—Fe1	−59.37 (17)	C14—C15—C16—C17	−56.0 (4)
C2—C3—C4—C5	−0.1 (3)	C15—C16—C17—C12	55.3 (4)
Fe1—C3—C4—C5	58.98 (18)	C13—C12—C17—C16	−54.5 (4)
C2—C3—C4—Fe1	−59.09 (18)	P1—C12—C17—C16	178.3 (2)
C3—C4—C5—C1	0.7 (3)	C1—P1—C12'—C13'	−39 (2)
Fe1—C4—C5—C1	59.84 (17)	C6—P1—C12'—C13'	72 (2)
C3—C4—C5—Fe1	−59.18 (18)	Zn1'—P1—C12'—C13'	−150.8 (19)
C2—C1—C5—C4	−0.9 (3)	C1—P1—C12'—C17'	−176.2 (15)
P1—C1—C5—C4	176.90 (18)	C6—P1—C12'—C17'	−64.7 (18)
Fe1—C1—C5—C4	−59.59 (17)	Zn1'—P1—C12'—C17'	72.1 (17)
C2—C1—C5—Fe1	58.64 (17)	C17'—C12'—C13'—C14'	−47 (3)
P1—C1—C5—Fe1	−123.51 (19)	P1—C12'—C13'—C14'	176.3 (18)
C1—P1—C6—C11	64.1 (2)	C12'—C13'—C14'—C15'	37 (3)
C12'—P1—C6—C11	−42.4 (7)	C13'—C14'—C15'—C16'	−38 (3)
C12—P1—C6—C11	−47.9 (2)	C14'—C15'—C16'—C17'	47 (3)
Zn1—P1—C6—C11	−175.55 (16)	C13'—C12'—C17'—C16'	56 (2)
Zn1'—P1—C6—C11	−175.3 (3)	P1—C12'—C17'—C16'	−165.1 (14)
C1—P1—C6—C7	−170.50 (18)	C15'—C16'—C17'—C12'	−55 (2)

Symmetry code: (i) x, −y+3/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cl2b	0.95	2.83	3.500 (16)	128

Selected bond lengths (Å) and angles (°) for 1, 2, 3 and 4 top

1		2		3		4
Cd1—O1	2.187 (5)	Zn1—O2	1.934 (2)	S1—P1	1.9581 (9)	Zn1—P1	2.4089 (16)
Cd1—Cl1	2.417 (8)	Zn1—O3ⁱ	1.936 (2)	S2—P2	1.9604 (10)	Zn1—C18	1.965 (6)
Cd1—Cl2	2.398 (3)	Zn1—O1	1.980 (2)	P1—C1	1.810 (3)	Zn1—C19	2.055 (6)
Cd1—P2	2.567 (3)	Zn1—Cl1	2.2092 (10)	P2—C6	1.810 (3)	P1—C6	1.841 (3)
P1—O1	1.493 (5)	P1—O1	1.498 (2)	P1—C11	1.870 (2)	P1—C12	1.868 (3)
O1—Cd1—Cl1	103.8 (6)	P2—O2	1.498 (2)	P1—C15	1.889 (3)	N1—C18	1.174 (7)
O1—Cd1—Cl2	107.4 (2)	P2—O3	1.500 (2)	P2—C23	1.878 (2)	N2—C19	1.081 (8)
Cl1—Cd1—Cl2	113.8 (9)	O2—Zn1—O3ⁱ	114.14 (10)	P2—C19	1.878 (2)	Zn1—Cl1	2.274 (13)
O1—Cd1—P2	102.3 (2)	O2—Zn1—O1	103.13 (10)	C1—P1—S1	111.75 (8)	Zn1—Cl2	2.288 (13)
Cl1—Cd1—P2	113.2 (6)	O3ⁱ—Zn1—O1	106.03 (10)	C11—P1—S1	110.08 (9)	C18—Zn1—C19	108.8 (5)
Cl2—Cd1—P2	114.84 (12)	O2—Zn1—Cl1	112.26 (7)	C15—P1—S1	112.57 (9)	C18—Zn1—P1	117.88 (15)
O1—P1—C1	109.8 (3)	O3ⁱ—Zn1—Cl1	112.38 (8)	C6—P2—S2	111.11 (9)	C19—Zn1—P1	103.6 (2)
O1—P1—C17	118.1 (3)	O1—Zn1—Cl1	108.08 (7)	C23—P2—S2	111.07 (9)	N1—C18—Zn1	172.6 (8)
O1—P1—C11	104.3 (4)	O2—P2—O3	116.01 (14)	C19—P2—S2	111.56 (9)	N2—C19—Zn1	173.7 (11)
P1—O1—Cd1	153.9 (5)	O2—P2—C23	107.44 (15)			P1—Zn1—P1ⁱⁱ	103.30 (9)
O1—P1—C1	117.5 (3)	O3—P2—C23	108.32 (15)
		P1—O1—Zn1	141.30 (15)
		P2—O2—Zn1	142.92 (15)
		P2—O3—Zn1ⁱ	151.38 (15)

Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x, -y+3/2, z.

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Transition-metal complexes of group 12 with 1,1′-bis­(phosphan­yl)ferrocene ligands

Supporting information

Transition-metal complexes of group 12 with 1,1′-bis(phosphanyl)ferrocene ligands