Synthesis and structural elucidation of new complexes of 2,4- and 3,5-dimethyl diphenyldithiophosphates with cobalt(II)

Kumar, S.; Khajuria, R.; Jassal, A.K.; Hundal, M.S.; Pandey, S.K.

doi:10.1107/S205252061500390X

Synthesis and structural elucidation of new complexes of 2,4- and 3,5-dimethyl diphenyldithiophosphates with cobalt(II)

S. Kumar, R. Khajuria, A. K. Jassal, M. S. Hundal and S. K. Pandey

A new series of donor-stabilized addition complexes of cobalt(II) with disubstituted diphenyldithiophosphates [{(ArO)₂PS₂}₂CoL₂] {Ar = 2,4-(CH₃)₂C₆H₃ [(1)-(3)] and 3,5-(CH₃)₂C₆H₃ [(4)-(6)]; L = C₅H₅N [(1), (4)], 3,4-(CH₃)₂C₅H₃N [(2), (5)] and 4-(C₂H₅)C₅H₄N [(3), (6)]} were successfully isolated and characterized by elemental analyses, magnetic moment measurements, IR and single-crystal X-ray analysis. Complexes (3), (4) and (5) crystallize in the monoclinic space groups P2₁/n, P2₁/n and P2₁/c, respectively, whereas complex (6) crystallizes in the triclinic space group $P\bar 1$ . X-ray diffraction analysis of complexes (3)-(6) reveals a six-coordinated distorted octahedral geometry for the CoS₄N₂ chromophore defined by two chelating diphenyldithiophosphate anions as well as two N-donor ligands. Two diphenyldithiophosphate ligands are coordinated to the cobalt ion as a bidentate ligand chelating via the two thiolate S atoms. Each of them forms a four-membered chelate ring in the equatorial plane. The N atoms from two donor ligands are axially coordinated to the Co atom in a mutually trans position.

Keywords: diphenyldithiophosphate; chromophore; donor stabilized.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S205252061500390X/bp5076sup1.cif Contains datablocks 24COETPY_0m, 35Co_jammu_0m, 35_Co_DIPY_0m, 35_Co_ETPY_0m
	Structure factor file (CIF format) https://doi.org/10.1107/S205252061500390X/bp507624COETPY_0msup2.hkl Contains datablock shelxl
	Structure factor file (CIF format) https://doi.org/10.1107/S205252061500390X/bp507635Co_jammu_0msup3.hkl Contains datablock shelxl
	Structure factor file (CIF format) https://doi.org/10.1107/S205252061500390X/bp507635_Co_DIPY_0msup4.hkl Contains datablock shelxl
	Structure factor file (CIF format) https://doi.org/10.1107/S205252061500390X/bp507635_Co_ETPY_0msup5.hkl Contains datablock shelxl

CCDC references: 1051253; 1051254; 1051255; 1051256

Experimental top

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Results and discussion top

Computing details top

For all compounds, data collection: Bruker APEX2; cell refinement: Bruker SAINT; data reduction: Bruker SAINT. Program(s) used to solve structure: Sir-92 (Altomare et al., 1993) for 24COETPY_0m, 35_Co_DIPY_0m, 35_Co_ETPY_0m; Sir-92 (Sheldrick, 1993) for 35Co_jammu_0m. Program(s) used to refine structure: SHELXL2014 (Sheldrick 2014) for 24COETPY_0m; SHELXL97 (Sheldrick, 2008) for 35Co_jammu_0m, 35_Co_DIPY_0m, 35_Co_ETPY_0m. For all compounds, molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.

Figures top

(24COETPY_0m) top

Crystal data top

C₄₆H₅₄CoN₂O₄P₂S₄	F(000) = 994
M_r = 948.06	D_x = 1.308 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5660 reflections
a = 10.254 (3) Å	θ = 2.4–26.2°
b = 15.557 (5) Å	µ = 0.64 mm⁻¹
c = 15.444 (6) Å	T = 296 K
β = 102.287 (5)°	Rectangular, pink
V = 2407.2 (14) Å³	0.15 × 0.12 × 0.08 mm
Z = 2

Data collection top

Bruker APEX-II CCD diffractometer	5308 independent reflections
Radiation source: fine-focus sealed tube	3263 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan SADABS2014/2 - Bruker AXS area detector scaling and absorption correction	h = −12→13
T_min = 0.626, T_max = 0.746	k = −18→19
19203 measured reflections	l = −19→19

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.256	w = 1/[σ²(F_o²) + (0.1698P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.003
5308 reflections	Δρ_max = 0.66 e Å⁻³
273 parameters	Δρ_min = −0.58 e Å⁻³
1 restraint

Crystal data top

C₄₆H₅₄CoN₂O₄P₂S₄	V = 2407.2 (14) Å³
M_r = 948.06	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.254 (3) Å	µ = 0.64 mm⁻¹
b = 15.557 (5) Å	T = 296 K
c = 15.444 (6) Å	0.15 × 0.12 × 0.08 mm
β = 102.287 (5)°

Data collection top

Bruker APEX-II CCD diffractometer	5308 independent reflections
Absorption correction: multi-scan SADABS2014/2 - Bruker AXS area detector scaling and absorption correction	3263 reflections with I > 2σ(I)
T_min = 0.626, T_max = 0.746	R_int = 0.066
19203 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	273 parameters
wR(F²) = 0.256	1 restraint
S = 1.00	Δρ_max = 0.66 e Å⁻³
5308 reflections	Δρ_min = −0.58 e Å⁻³

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
C1	0.6455 (5)	−0.1630 (3)	0.4584 (3)	0.0570 (12)
H1	0.5949	−0.1879	0.4950	0.068*
C2	0.7280 (6)	−0.2151 (4)	0.4211 (4)	0.0766 (17)
H2	0.7337	−0.2734	0.4347	0.092*
C3	0.8013 (6)	−0.1820 (5)	0.3646 (4)	0.0819 (18)
C4	0.7922 (5)	−0.0936 (4)	0.3507 (4)	0.0692 (15)
H4	0.8432	−0.0673	0.3153	0.083*
C5	0.7088 (5)	−0.0457 (4)	0.3890 (3)	0.0558 (12)
H5	0.7018	0.0128	0.3767	0.067*
C6	0.8973 (11)	−0.2302 (8)	0.3223 (8)	0.157 (4)
H6A	0.8818	−0.2131	0.2606	0.188*
H6B	0.9867	−0.2117	0.3501	0.188*
C7	0.8945 (19)	−0.3209 (9)	0.3254 (12)	0.300 (13)
H7A	0.9253	−0.3398	0.3854	0.450*
H7B	0.9514	−0.3439	0.2891	0.450*
H7C	0.8048	−0.3406	0.3037	0.450*
C8	0.9068 (4)	−0.0751 (3)	0.6851 (3)	0.0443 (10)
C9	0.9137 (5)	−0.1503 (3)	0.7341 (3)	0.0541 (12)
C10	0.9771 (5)	−0.2197 (4)	0.7035 (4)	0.0684 (15)
H10	0.9816	−0.2717	0.7337	0.082*
C11	1.0329 (6)	−0.2142 (4)	0.6306 (4)	0.0718 (16)
C12	1.0241 (5)	−0.1364 (4)	0.5827 (4)	0.0675 (14)
H12	1.0613	−0.1320	0.5329	0.081*
C13	0.9609 (5)	−0.0682 (3)	0.6098 (3)	0.0552 (12)
H13	0.9536	−0.0168	0.5782	0.066*
C14	0.8560 (6)	−0.1576 (4)	0.8156 (4)	0.0713 (15)
H14A	0.8873	−0.1107	0.8549	0.107*
H14B	0.8835	−0.2110	0.8451	0.107*
H14C	0.7604	−0.1558	0.7989	0.107*
C15	1.0965 (8)	−0.2929 (4)	0.5982 (6)	0.113 (3)
H15A	1.0830	−0.3420	0.6330	0.170*
H15B	1.1904	−0.2832	0.6041	0.170*
H15C	1.0562	−0.3033	0.5371	0.170*
C16	0.7088 (5)	0.0693 (3)	0.8366 (3)	0.0468 (10)
C17	0.8189 (5)	0.1063 (3)	0.8887 (3)	0.0513 (11)
C18	0.8508 (6)	0.0829 (4)	0.9780 (3)	0.0618 (13)
H18	0.9258	0.1073	1.0142	0.074*
C19	0.7758 (6)	0.0253 (4)	1.0148 (3)	0.0646 (14)
C20	0.6610 (7)	−0.0080 (4)	0.9600 (4)	0.0720 (16)
H20	0.6060	−0.0451	0.9832	0.086*
C21	0.6287 (6)	0.0141 (3)	0.8709 (4)	0.0614 (14)
H21	0.5525	−0.0086	0.8345	0.074*
C22	0.9006 (6)	0.1710 (4)	0.8517 (4)	0.0751 (17)
H22A	0.9371	0.1447	0.8059	0.113*
H22B	0.9719	0.1910	0.8981	0.113*
H22C	0.8451	0.2186	0.8275	0.113*
C23	0.8121 (9)	0.0008 (5)	1.1112 (4)	0.100 (3)
H23A	0.8598	−0.0527	1.1175	0.150*
H23B	0.7323	−0.0053	1.1338	0.150*
H23C	0.8674	0.0448	1.1438	0.150*
N1	0.6354 (3)	−0.0793 (3)	0.4442 (2)	0.0467 (9)
O1	0.8483 (3)	−0.00222 (19)	0.7150 (2)	0.0492 (8)
O2	0.6755 (3)	0.0920 (2)	0.7464 (2)	0.0527 (8)
P1	0.69987 (11)	0.02875 (8)	0.66949 (7)	0.0430 (3)
S1	0.57729 (11)	−0.07019 (8)	0.64783 (7)	0.0486 (3)
S2	0.69195 (12)	0.10061 (8)	0.56350 (7)	0.0495 (3)
Co1	0.5000	0.0000	0.5000	0.0407 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.062 (3)	0.050 (3)	0.067 (3)	0.000 (2)	0.029 (2)	0.005 (2)
C2	0.092 (4)	0.057 (3)	0.093 (4)	0.010 (3)	0.046 (4)	0.000 (3)
C3	0.079 (4)	0.090 (5)	0.092 (4)	0.008 (3)	0.052 (3)	−0.002 (4)
C4	0.063 (3)	0.089 (4)	0.065 (3)	−0.012 (3)	0.036 (3)	−0.005 (3)
C5	0.057 (3)	0.063 (3)	0.050 (3)	−0.007 (2)	0.018 (2)	0.002 (2)
C6	0.189 (10)	0.144 (9)	0.178 (10)	0.014 (8)	0.130 (9)	−0.038 (8)
C7	0.41 (3)	0.250 (18)	0.31 (2)	0.18 (2)	0.25 (2)	0.019 (17)
C8	0.036 (2)	0.050 (3)	0.044 (2)	−0.0004 (18)	0.0010 (18)	−0.0050 (19)
C9	0.044 (2)	0.063 (3)	0.051 (3)	0.001 (2)	0.001 (2)	0.005 (2)
C10	0.062 (3)	0.055 (3)	0.084 (4)	0.003 (3)	0.005 (3)	0.002 (3)
C11	0.060 (3)	0.068 (4)	0.085 (4)	0.014 (3)	0.009 (3)	−0.008 (3)
C12	0.061 (3)	0.075 (4)	0.070 (3)	0.006 (3)	0.023 (3)	−0.012 (3)
C13	0.047 (3)	0.064 (3)	0.055 (3)	−0.002 (2)	0.012 (2)	0.007 (2)
C14	0.067 (3)	0.084 (4)	0.059 (3)	0.004 (3)	0.005 (3)	0.018 (3)
C15	0.127 (7)	0.080 (5)	0.135 (7)	0.034 (5)	0.034 (6)	−0.020 (5)
C16	0.053 (3)	0.049 (3)	0.039 (2)	0.006 (2)	0.0131 (19)	0.0007 (19)
C17	0.060 (3)	0.052 (3)	0.044 (2)	−0.003 (2)	0.016 (2)	−0.006 (2)
C18	0.070 (3)	0.068 (3)	0.045 (3)	−0.005 (3)	0.006 (2)	−0.009 (2)
C19	0.080 (4)	0.071 (4)	0.043 (3)	0.003 (3)	0.013 (3)	0.001 (3)
C20	0.078 (4)	0.089 (5)	0.057 (3)	−0.007 (3)	0.032 (3)	0.007 (3)
C21	0.061 (3)	0.071 (4)	0.054 (3)	−0.012 (3)	0.017 (2)	−0.008 (2)
C22	0.093 (4)	0.072 (4)	0.062 (3)	−0.029 (3)	0.020 (3)	−0.011 (3)
C23	0.135 (7)	0.118 (6)	0.046 (3)	0.004 (4)	0.016 (4)	0.013 (3)
N1	0.045 (2)	0.059 (3)	0.0388 (18)	−0.0038 (17)	0.0132 (16)	0.0013 (17)
O1	0.0477 (19)	0.052 (2)	0.0443 (17)	0.0005 (13)	0.0014 (14)	−0.0057 (13)
O2	0.0622 (19)	0.0565 (19)	0.0387 (16)	0.0051 (15)	0.0094 (14)	−0.0021 (14)
P1	0.0428 (6)	0.0508 (7)	0.0338 (6)	−0.0017 (5)	0.0046 (4)	−0.0017 (5)
S1	0.0504 (7)	0.0552 (7)	0.0384 (6)	−0.0079 (5)	0.0050 (5)	0.0062 (5)
S2	0.0516 (7)	0.0550 (7)	0.0408 (6)	−0.0098 (5)	0.0076 (5)	0.0054 (5)
Co1	0.0410 (5)	0.0495 (6)	0.0317 (4)	−0.0031 (3)	0.0078 (3)	0.0017 (3)

Geometric parameters (Å, º) top

C1—N1	1.320 (6)	C15—H15A	0.9600
C1—C2	1.383 (7)	C15—H15B	0.9600
C1—H1	0.9300	C15—H15C	0.9600
C2—C3	1.368 (8)	C16—C17	1.366 (6)
C2—H2	0.9300	C16—C21	1.371 (7)
C3—C4	1.391 (9)	C16—O2	1.406 (5)
C3—C6	1.494 (10)	C17—C18	1.395 (7)
C4—C5	1.360 (7)	C17—C22	1.498 (7)
C4—H4	0.9300	C18—C19	1.381 (8)
C5—N1	1.356 (6)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.395 (8)
C6—C7	1.412 (19)	C19—C23	1.505 (8)
C6—H6A	0.9700	C20—C21	1.388 (8)
C6—H6B	0.9700	C20—H20	0.9300
C7—H7A	0.9600	C21—H21	0.9300
C7—H7B	0.9600	C22—H22A	0.9600
C7—H7C	0.9600	C22—H22B	0.9600
C8—C9	1.386 (6)	C22—H22C	0.9600
C8—C13	1.396 (6)	C23—H23A	0.9600
C8—O1	1.406 (5)	C23—H23B	0.9600
C9—C10	1.393 (7)	C23—H23C	0.9600
C9—C14	1.505 (7)	N1—Co1	2.168 (4)
C10—C11	1.370 (9)	O1—P1	1.608 (3)
C10—H10	0.9300	O2—P1	1.602 (3)
C11—C12	1.411 (8)	P1—S2	1.9696 (17)
C11—C15	1.521 (8)	P1—S1	1.9702 (17)
C12—C13	1.356 (7)	S1—Co1	2.5026 (13)
C12—H12	0.9300	S2—Co1	2.5425 (13)
C13—H13	0.9300	Co1—N1ⁱ	2.168 (4)
C14—H14A	0.9600	Co1—S1ⁱ	2.5026 (13)
C14—H14B	0.9600	Co1—S2ⁱ	2.5425 (13)
C14—H14C	0.9600

N1—C1—C2	122.9 (5)	C17—C16—O2	118.3 (4)
N1—C1—H1	118.6	C21—C16—O2	120.1 (4)
C2—C1—H1	118.6	C16—C17—C18	117.6 (5)
C3—C2—C1	120.8 (6)	C16—C17—C22	121.1 (4)
C3—C2—H2	119.6	C18—C17—C22	121.3 (5)
C1—C2—H2	119.6	C19—C18—C17	122.8 (5)
C2—C3—C4	116.2 (5)	C19—C18—H18	118.6
C2—C3—C6	126.4 (7)	C17—C18—H18	118.6
C4—C3—C6	117.2 (7)	C18—C19—C20	117.6 (5)
C5—C4—C3	120.2 (5)	C18—C19—C23	122.0 (6)
C5—C4—H4	119.9	C20—C19—C23	120.4 (6)
C3—C4—H4	119.9	C21—C20—C19	120.1 (5)
N1—C5—C4	123.1 (5)	C21—C20—H20	119.9
N1—C5—H5	118.4	C19—C20—H20	119.9
C4—C5—H5	118.4	C16—C21—C20	120.2 (5)
C7—C6—C3	117.8 (9)	C16—C21—H21	119.9
C7—C6—H6A	107.8	C20—C21—H21	119.9
C3—C6—H6A	107.8	C17—C22—H22A	109.5
C7—C6—H6B	107.9	C17—C22—H22B	109.5
C3—C6—H6B	107.9	H22A—C22—H22B	109.5
H6A—C6—H6B	107.2	C17—C22—H22C	109.5
C6—C7—H7A	109.5	H22A—C22—H22C	109.5
C6—C7—H7B	109.5	H22B—C22—H22C	109.5
H7A—C7—H7B	109.5	C19—C23—H23A	109.5
C6—C7—H7C	109.5	C19—C23—H23B	109.5
H7A—C7—H7C	109.5	H23A—C23—H23B	109.5
H7B—C7—H7C	109.5	C19—C23—H23C	109.5
C9—C8—C13	122.5 (4)	H23A—C23—H23C	109.5
C9—C8—O1	118.5 (4)	H23B—C23—H23C	109.5
C13—C8—O1	118.9 (4)	C1—N1—C5	116.7 (4)
C8—C9—C10	116.2 (5)	C1—N1—Co1	122.0 (3)
C8—C9—C14	122.4 (5)	C5—N1—Co1	121.2 (3)
C10—C9—C14	121.4 (5)	C8—O1—P1	121.9 (3)
C11—C10—C9	122.5 (5)	C16—O2—P1	122.5 (3)
C11—C10—H10	118.8	O2—P1—O1	98.16 (17)
C9—C10—H10	118.8	O2—P1—S2	106.42 (14)
C10—C11—C12	119.6 (5)	O1—P1—S2	113.65 (14)
C10—C11—C15	120.2 (6)	O2—P1—S1	114.25 (14)
C12—C11—C15	120.1 (6)	O1—P1—S1	110.51 (13)
C13—C12—C11	119.4 (5)	S2—P1—S1	112.98 (7)
C13—C12—H12	120.3	P1—S1—Co1	83.15 (5)
C11—C12—H12	120.3	P1—S2—Co1	82.11 (5)
C12—C13—C8	119.8 (5)	N1—Co1—N1ⁱ	179.999 (1)
C12—C13—H13	120.1	N1—Co1—S1	90.52 (10)
C8—C13—H13	120.1	N1ⁱ—Co1—S1	89.48 (10)
C9—C14—H14A	109.5	N1—Co1—S1ⁱ	89.48 (10)
C9—C14—H14B	109.5	N1ⁱ—Co1—S1ⁱ	90.52 (10)
H14A—C14—H14B	109.5	S1—Co1—S1ⁱ	180.0
C9—C14—H14C	109.5	N1—Co1—S2	89.73 (10)
H14A—C14—H14C	109.5	N1ⁱ—Co1—S2	90.27 (10)
H14B—C14—H14C	109.5	S1—Co1—S2	81.25 (4)
C11—C15—H15A	109.5	S1ⁱ—Co1—S2	98.75 (4)
C11—C15—H15B	109.5	N1—Co1—S2ⁱ	90.27 (10)
H15A—C15—H15B	109.5	N1ⁱ—Co1—S2ⁱ	89.73 (10)
C11—C15—H15C	109.5	S1—Co1—S2ⁱ	98.75 (4)
H15A—C15—H15C	109.5	S1ⁱ—Co1—S2ⁱ	81.25 (4)
H15B—C15—H15C	109.5	S2—Co1—S2ⁱ	180.0
C17—C16—C21	121.6 (4)

N1—C1—C2—C3	−2.0 (10)	C2—C1—N1—Co1	177.9 (4)
C1—C2—C3—C4	2.9 (10)	C4—C5—N1—C1	−1.6 (7)
C1—C2—C3—C6	177.8 (8)	C4—C5—N1—Co1	−178.2 (4)
C2—C3—C4—C5	−3.2 (10)	C9—C8—O1—P1	−103.4 (4)
C6—C3—C4—C5	−178.5 (7)	C13—C8—O1—P1	79.4 (5)
C3—C4—C5—N1	2.6 (9)	C17—C16—O2—P1	105.7 (4)
C2—C3—C6—C7	13.7 (19)	C21—C16—O2—P1	−76.8 (5)
C4—C3—C6—C7	−171.4 (14)	C16—O2—P1—O1	−44.9 (4)
C13—C8—C9—C10	−0.6 (7)	C16—O2—P1—S2	−162.5 (3)
O1—C8—C9—C10	−177.7 (4)	C16—O2—P1—S1	72.1 (4)
C13—C8—C9—C14	179.6 (4)	C8—O1—P1—O2	164.0 (3)
O1—C8—C9—C14	2.5 (6)	C8—O1—P1—S2	−84.0 (3)
C8—C9—C10—C11	1.6 (7)	C8—O1—P1—S1	44.3 (4)
C14—C9—C10—C11	−178.5 (5)	O2—P1—S1—Co1	115.43 (14)
C9—C10—C11—C12	−1.5 (9)	O1—P1—S1—Co1	−135.02 (14)
C9—C10—C11—C15	−177.8 (6)	S2—P1—S1—Co1	−6.42 (7)
C10—C11—C12—C13	0.3 (8)	O2—P1—S2—Co1	−119.82 (14)
C15—C11—C12—C13	176.5 (6)	O1—P1—S2—Co1	133.29 (13)
C11—C12—C13—C8	0.8 (8)	S1—P1—S2—Co1	6.34 (7)
C9—C8—C13—C12	−0.6 (7)	C1—N1—Co1—S1	46.4 (4)
O1—C8—C13—C12	176.5 (4)	C5—N1—Co1—S1	−137.1 (3)
C21—C16—C17—C18	2.8 (7)	C1—N1—Co1—S1ⁱ	−133.6 (4)
O2—C16—C17—C18	−179.8 (4)	C5—N1—Co1—S1ⁱ	42.9 (3)
C21—C16—C17—C22	−175.9 (5)	C1—N1—Co1—S2	127.7 (4)
O2—C16—C17—C22	1.5 (7)	C5—N1—Co1—S2	−55.8 (3)
C16—C17—C18—C19	−0.4 (8)	C1—N1—Co1—S2ⁱ	−52.3 (4)
C22—C17—C18—C19	178.3 (5)	C5—N1—Co1—S2ⁱ	124.2 (3)
C17—C18—C19—C20	−2.3 (9)	P1—S1—Co1—N1	94.28 (11)
C17—C18—C19—C23	179.9 (6)	P1—S1—Co1—N1ⁱ	−85.72 (11)
C18—C19—C20—C21	2.7 (9)	P1—S1—Co1—S2	4.63 (5)
C23—C19—C20—C21	−179.4 (6)	P1—S1—Co1—S2ⁱ	−175.37 (5)
C17—C16—C21—C20	−2.3 (8)	P1—S2—Co1—N1	−95.21 (11)
O2—C16—C21—C20	−179.7 (5)	P1—S2—Co1—N1ⁱ	84.79 (11)
C19—C20—C21—C16	−0.5 (9)	P1—S2—Co1—S1	−4.64 (5)
C2—C1—N1—C5	1.2 (8)	P1—S2—Co1—S1ⁱ	175.36 (5)

Symmetry code: (i) −x+1, −y, −z+1.

(35Co_jammu_0m) top

Crystal data top

C₄₂H₄₆CoN₂O₄P₂S₄	F(000) = 930
M_r = 891.96	D_x = 1.397 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9916 reflections
a = 11.8107 (6) Å	θ = 3.6–29.8°
b = 14.4211 (9) Å	µ = 0.72 mm⁻¹
c = 12.8807 (7) Å	T = 296 K
β = 104.929 (2)°	Rectangular, pink
V = 2119.8 (2) Å³	0.10 × 0.07 × 0.05 mm
Z = 2

Data collection top

Bruker APEX-II CCD diffractometer	6024 independent reflections
Radiation source: fine-focus sealed tube	5025 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 29.9°, θ_min = 2.1°
Absorption correction: multi-scan SADABS2008/1 - Bruker AXS area detector scaling and absorption correction	h = −16→16
T_min = 0.648, T_max = 0.746	k = −10→20
22789 measured reflections	l = −15→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0429P)² + 0.7639P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.025
6024 reflections	Δρ_max = 0.31 e Å⁻³
254 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints

Crystal data top

C₄₂H₄₆CoN₂O₄P₂S₄	V = 2119.8 (2) Å³
M_r = 891.96	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.8107 (6) Å	µ = 0.72 mm⁻¹
b = 14.4211 (9) Å	T = 296 K
c = 12.8807 (7) Å	0.10 × 0.07 × 0.05 mm
β = 104.929 (2)°

Data collection top

Bruker APEX-II CCD diffractometer	6024 independent reflections
Absorption correction: multi-scan SADABS2008/1 - Bruker AXS area detector scaling and absorption correction	5025 reflections with I > 2σ(I)
T_min = 0.648, T_max = 0.746	R_int = 0.020
22789 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	254 parameters
wR(F²) = 0.087	0 restraints
S = 1.03	Δρ_max = 0.31 e Å⁻³
6024 reflections	Δρ_min = −0.28 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
C1	0.42335 (16)	0.15185 (13)	0.82653 (14)	0.0432 (4)
H1	0.4221	0.1870	0.8867	0.052*
C2	0.38803 (18)	0.19319 (16)	0.72693 (17)	0.0569 (5)
H2	0.3637	0.2547	0.7205	0.068*
C3	0.38940 (18)	0.14217 (17)	0.63776 (15)	0.0575 (5)
H3	0.3650	0.1681	0.5695	0.069*
C4	0.42773 (19)	0.05157 (17)	0.65107 (14)	0.0555 (5)
H4	0.4306	0.0155	0.5919	0.067*
C5	0.46180 (16)	0.01512 (13)	0.75369 (13)	0.0407 (4)
H5	0.4876	−0.0460	0.7622	0.049*
C6	0.87330 (12)	0.13137 (11)	0.94131 (11)	0.0299 (3)
C7	0.98321 (12)	0.16482 (11)	0.94266 (12)	0.0321 (3)
H7	1.0467	0.1516	1.0004	0.039*
C8	0.99873 (13)	0.21807 (11)	0.85774 (13)	0.0344 (3)
C9	0.90195 (14)	0.23660 (12)	0.77278 (12)	0.0367 (3)
H9	0.9116	0.2722	0.7155	0.044*
C10	0.79156 (13)	0.20339 (12)	0.77121 (12)	0.0372 (3)
C11	0.77661 (13)	0.14994 (12)	0.85681 (12)	0.0365 (3)
H11	0.7031	0.1271	0.8572	0.044*
C12	1.11791 (15)	0.25417 (16)	0.85637 (17)	0.0550 (5)
H12A	1.1340	0.3099	0.8984	0.082*
H12B	1.1195	0.2673	0.7837	0.082*
H12C	1.1762	0.2083	0.8862	0.082*
C13	0.68800 (16)	0.22492 (18)	0.67768 (15)	0.0566 (5)
H13A	0.6318	0.2610	0.7024	0.085*
H13B	0.6524	0.1681	0.6468	0.085*
H13C	0.7141	0.2594	0.6244	0.085*
C14	0.91012 (12)	0.02971 (11)	1.25315 (11)	0.0298 (3)
C15	0.87586 (14)	0.06755 (12)	1.33859 (12)	0.0352 (3)
H15	0.7974	0.0674	1.3395	0.042*
C16	0.96051 (15)	0.10594 (12)	1.42355 (12)	0.0385 (3)
C17	1.07654 (15)	0.10471 (12)	1.41935 (13)	0.0409 (4)
H17	1.1331	0.1314	1.4753	0.049*
C18	1.11101 (14)	0.06494 (12)	1.33448 (13)	0.0378 (3)
C19	1.02548 (13)	0.02745 (11)	1.24933 (12)	0.0330 (3)
H19	1.0461	0.0013	1.1908	0.040*
C20	0.9275 (2)	0.14638 (15)	1.51987 (14)	0.0534 (5)
H20A	0.8716	0.1066	1.5401	0.080*
H20B	0.8937	0.2067	1.5021	0.080*
H20C	0.9962	0.1515	1.5787	0.080*
C21	1.23878 (16)	0.05799 (18)	1.33528 (17)	0.0567 (5)
H21A	1.2739	0.0068	1.3796	0.085*
H21B	1.2782	0.1143	1.3634	0.085*
H21C	1.2454	0.0485	1.2633	0.085*
N1	0.45928 (10)	0.06395 (9)	0.84110 (10)	0.0311 (3)
O1	0.82571 (9)	−0.01499 (8)	1.17053 (8)	0.0330 (2)
O2	0.86919 (9)	0.07617 (9)	1.02883 (9)	0.0395 (3)
P1	0.75805 (3)	0.03339 (3)	1.06066 (3)	0.02718 (8)
S1	0.64619 (3)	0.12978 (3)	1.07864 (3)	0.03372 (9)
S2	0.68179 (3)	−0.06765 (3)	0.96426 (3)	0.03288 (9)
Co1	0.5000	0.0000	1.0000	0.02581 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0481 (9)	0.0382 (9)	0.0422 (9)	0.0063 (7)	0.0100 (7)	0.0035 (7)
C2	0.0564 (11)	0.0514 (11)	0.0589 (12)	0.0095 (9)	0.0074 (9)	0.0208 (10)
C3	0.0543 (11)	0.0710 (14)	0.0378 (9)	−0.0104 (10)	−0.0050 (8)	0.0177 (9)
C4	0.0654 (12)	0.0688 (14)	0.0285 (8)	−0.0144 (10)	0.0051 (8)	−0.0040 (8)
C5	0.0468 (9)	0.0424 (9)	0.0310 (7)	−0.0027 (7)	0.0068 (7)	−0.0033 (6)
C6	0.0283 (7)	0.0363 (7)	0.0250 (6)	−0.0025 (5)	0.0065 (5)	0.0039 (5)
C7	0.0261 (6)	0.0376 (8)	0.0305 (7)	−0.0026 (5)	0.0035 (5)	0.0021 (6)
C8	0.0301 (7)	0.0356 (8)	0.0382 (8)	−0.0025 (6)	0.0098 (6)	0.0045 (6)
C9	0.0375 (8)	0.0399 (8)	0.0332 (7)	−0.0005 (6)	0.0100 (6)	0.0094 (6)
C10	0.0321 (7)	0.0461 (9)	0.0305 (7)	0.0006 (6)	0.0029 (6)	0.0077 (6)
C11	0.0268 (7)	0.0490 (9)	0.0320 (7)	−0.0037 (6)	0.0046 (6)	0.0071 (7)
C12	0.0348 (9)	0.0643 (13)	0.0648 (12)	−0.0091 (8)	0.0112 (8)	0.0246 (10)
C13	0.0402 (9)	0.0801 (15)	0.0420 (9)	−0.0036 (9)	−0.0032 (7)	0.0240 (10)
C14	0.0305 (7)	0.0323 (7)	0.0230 (6)	−0.0026 (5)	0.0004 (5)	0.0048 (5)
C15	0.0342 (7)	0.0409 (8)	0.0301 (7)	0.0038 (6)	0.0077 (6)	0.0050 (6)
C16	0.0500 (9)	0.0384 (8)	0.0253 (7)	0.0062 (7)	0.0068 (6)	0.0019 (6)
C17	0.0436 (9)	0.0428 (9)	0.0298 (7)	−0.0046 (7)	−0.0021 (6)	−0.0026 (7)
C18	0.0325 (7)	0.0423 (9)	0.0347 (7)	−0.0036 (6)	0.0016 (6)	0.0013 (7)
C19	0.0313 (7)	0.0385 (8)	0.0282 (7)	−0.0008 (6)	0.0060 (5)	0.0000 (6)
C20	0.0732 (13)	0.0555 (12)	0.0333 (8)	0.0100 (10)	0.0167 (8)	−0.0029 (8)
C21	0.0323 (9)	0.0775 (15)	0.0562 (11)	−0.0070 (9)	0.0037 (8)	−0.0054 (10)
N1	0.0283 (6)	0.0343 (6)	0.0286 (6)	−0.0011 (5)	0.0036 (4)	0.0003 (5)
O1	0.0312 (5)	0.0379 (6)	0.0260 (5)	−0.0062 (4)	0.0003 (4)	0.0053 (4)
O2	0.0254 (5)	0.0591 (8)	0.0318 (5)	−0.0053 (5)	0.0029 (4)	0.0164 (5)
P1	0.02309 (16)	0.03375 (19)	0.02315 (16)	−0.00309 (13)	0.00316 (12)	0.00194 (13)
S1	0.03446 (19)	0.03020 (18)	0.03455 (19)	−0.00159 (13)	0.00539 (14)	−0.00502 (14)
S2	0.02945 (17)	0.0372 (2)	0.02974 (17)	0.00332 (14)	0.00354 (13)	−0.00734 (14)
Co1	0.02387 (13)	0.02803 (14)	0.02411 (13)	−0.00024 (9)	0.00362 (9)	−0.00186 (10)

Geometric parameters (Å, º) top

C1—N1	1.334 (2)	C14—C19	1.376 (2)
C1—C2	1.378 (3)	C14—C15	1.379 (2)
C1—H1	0.9300	C14—O1	1.4125 (17)
C2—C3	1.368 (3)	C15—C16	1.393 (2)
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.379 (3)	C16—C17	1.385 (2)
C3—H3	0.9300	C16—C20	1.510 (2)
C4—C5	1.383 (3)	C17—C18	1.385 (2)
C4—H4	0.9300	C17—H17	0.9300
C5—N1	1.335 (2)	C18—C19	1.395 (2)
C5—H5	0.9300	C18—C21	1.510 (2)
C6—C7	1.3807 (19)	C19—H19	0.9300
C6—C11	1.386 (2)	C20—H20A	0.9600
C6—O2	1.3911 (17)	C20—H20B	0.9600
C7—C8	1.387 (2)	C20—H20C	0.9600
C7—H7	0.9300	C21—H21A	0.9600
C8—C9	1.390 (2)	C21—H21B	0.9600
C8—C12	1.505 (2)	C21—H21C	0.9600
C9—C10	1.384 (2)	N1—Co1	2.1827 (12)
C9—H9	0.9300	O1—P1	1.5954 (11)
C10—C11	1.393 (2)	O2—P1	1.5966 (11)
C10—C13	1.512 (2)	P1—S1	1.9721 (5)
C11—H11	0.9300	P1—S2	1.9748 (5)
C12—H12A	0.9600	S1—Co1	2.5708 (4)
C12—H12B	0.9600	S2—Co1	2.5065 (4)
C12—H12C	0.9600	Co1—N1ⁱ	2.1827 (12)
C13—H13A	0.9600	Co1—S2ⁱ	2.5065 (4)
C13—H13B	0.9600	Co1—S1ⁱ	2.5708 (4)
C13—H13C	0.9600

N1—C1—C2	123.42 (18)	C17—C16—C20	120.29 (16)
N1—C1—H1	118.3	C15—C16—C20	120.93 (16)
C2—C1—H1	118.3	C18—C17—C16	122.06 (15)
C3—C2—C1	118.9 (2)	C18—C17—H17	119.0
C3—C2—H2	120.6	C16—C17—H17	119.0
C1—C2—H2	120.6	C17—C18—C19	118.72 (15)
C2—C3—C4	118.68 (18)	C17—C18—C21	121.23 (15)
C2—C3—H3	120.7	C19—C18—C21	119.99 (16)
C4—C3—H3	120.7	C14—C19—C18	119.07 (14)
C3—C4—C5	118.98 (19)	C14—C19—H19	120.5
C3—C4—H4	120.5	C18—C19—H19	120.5
C5—C4—H4	120.5	C16—C20—H20A	109.5
N1—C5—C4	122.79 (18)	C16—C20—H20B	109.5
N1—C5—H5	118.6	H20A—C20—H20B	109.5
C4—C5—H5	118.6	C16—C20—H20C	109.5
C7—C6—C11	121.63 (13)	H20A—C20—H20C	109.5
C7—C6—O2	114.75 (12)	H20B—C20—H20C	109.5
C11—C6—O2	123.60 (13)	C18—C21—H21A	109.5
C6—C7—C8	119.89 (13)	C18—C21—H21B	109.5
C6—C7—H7	120.1	H21A—C21—H21B	109.5
C8—C7—H7	120.1	C18—C21—H21C	109.5
C7—C8—C9	118.59 (14)	H21A—C21—H21C	109.5
C7—C8—C12	120.98 (14)	H21B—C21—H21C	109.5
C9—C8—C12	120.42 (14)	C1—N1—C5	117.26 (14)
C10—C9—C8	121.71 (14)	C1—N1—Co1	121.23 (11)
C10—C9—H9	119.1	C5—N1—Co1	121.37 (11)
C8—C9—H9	119.1	C14—O1—P1	124.31 (10)
C9—C10—C11	119.39 (14)	C6—O2—P1	129.19 (9)
C9—C10—C13	120.42 (15)	O1—P1—O2	98.03 (6)
C11—C10—C13	120.19 (15)	O1—P1—S1	113.68 (5)
C6—C11—C10	118.79 (14)	O2—P1—S1	112.19 (5)
C6—C11—H11	120.6	O1—P1—S2	106.15 (5)
C10—C11—H11	120.6	O2—P1—S2	113.31 (5)
C8—C12—H12A	109.5	S1—P1—S2	112.52 (2)
C8—C12—H12B	109.5	P1—S1—Co1	80.956 (17)
H12A—C12—H12B	109.5	P1—S2—Co1	82.582 (16)
C8—C12—H12C	109.5	N1ⁱ—Co1—N1	180.0
H12A—C12—H12C	109.5	N1ⁱ—Co1—S2ⁱ	89.11 (3)
H12B—C12—H12C	109.5	N1—Co1—S2ⁱ	90.89 (3)
C10—C13—H13A	109.5	N1ⁱ—Co1—S2	90.89 (3)
C10—C13—H13B	109.5	N1—Co1—S2	89.11 (3)
H13A—C13—H13B	109.5	S2ⁱ—Co1—S2	180.0
C10—C13—H13C	109.5	N1ⁱ—Co1—S1	88.56 (3)
H13A—C13—H13C	109.5	N1—Co1—S1	91.44 (3)
H13B—C13—H13C	109.5	S2ⁱ—Co1—S1	99.465 (13)
C19—C14—C15	122.31 (14)	S2—Co1—S1	80.536 (13)
C19—C14—O1	118.38 (13)	N1ⁱ—Co1—S1ⁱ	91.44 (3)
C15—C14—O1	119.11 (13)	N1—Co1—S1ⁱ	88.56 (3)
C14—C15—C16	119.04 (14)	S2ⁱ—Co1—S1ⁱ	80.536 (13)
C14—C15—H15	120.5	S2—Co1—S1ⁱ	99.464 (13)
C16—C15—H15	120.5	S1—Co1—S1ⁱ	180.0
C17—C16—C15	118.77 (14)

N1—C1—C2—C3	0.0 (3)	C19—C14—O1—P1	−88.81 (16)
C1—C2—C3—C4	−0.9 (3)	C15—C14—O1—P1	96.19 (15)
C2—C3—C4—C5	0.9 (3)	C7—C6—O2—P1	173.77 (12)
C3—C4—C5—N1	0.0 (3)	C11—C6—O2—P1	−8.2 (2)
C11—C6—C7—C8	−0.3 (2)	C14—O1—P1—O2	49.69 (13)
O2—C6—C7—C8	177.83 (15)	C14—O1—P1—S1	−68.89 (12)
C6—C7—C8—C9	0.1 (2)	C14—O1—P1—S2	166.88 (10)
C6—C7—C8—C12	−179.05 (17)	C6—O2—P1—O1	−177.50 (14)
C7—C8—C9—C10	0.0 (3)	C6—O2—P1—S1	−57.78 (15)
C12—C8—C9—C10	179.21 (18)	C6—O2—P1—S2	70.99 (15)
C8—C9—C10—C11	0.0 (3)	O1—P1—S1—Co1	−104.49 (5)
C8—C9—C10—C13	179.89 (19)	O2—P1—S1—Co1	145.40 (5)
C7—C6—C11—C10	0.3 (3)	S2—P1—S1—Co1	16.22 (2)
O2—C6—C11—C10	−177.65 (16)	O1—P1—S2—Co1	108.37 (4)
C9—C10—C11—C6	−0.1 (3)	O2—P1—S2—Co1	−145.18 (5)
C13—C10—C11—C6	179.96 (18)	S1—P1—S2—Co1	−16.58 (2)
C19—C14—C15—C16	0.8 (2)	C1—N1—Co1—S2ⁱ	44.65 (12)
O1—C14—C15—C16	175.62 (14)	C5—N1—Co1—S2ⁱ	−130.86 (12)
C14—C15—C16—C17	−0.1 (2)	C1—N1—Co1—S2	−135.35 (12)
C14—C15—C16—C20	−178.73 (16)	C5—N1—Co1—S2	49.14 (12)
C15—C16—C17—C18	−1.3 (3)	C1—N1—Co1—S1	−54.85 (12)
C20—C16—C17—C18	177.37 (17)	C5—N1—Co1—S1	129.65 (12)
C16—C17—C18—C19	1.9 (3)	C1—N1—Co1—S1ⁱ	125.16 (12)
C16—C17—C18—C21	−175.42 (18)	C5—N1—Co1—S1ⁱ	−50.35 (12)
C15—C14—C19—C18	−0.2 (2)	P1—S2—Co1—N1ⁱ	−76.56 (4)
O1—C14—C19—C18	−175.06 (14)	P1—S2—Co1—N1	103.44 (4)
C17—C18—C19—C14	−1.1 (2)	P1—S2—Co1—S1	11.830 (16)
C21—C18—C19—C14	176.24 (16)	P1—S2—Co1—S1ⁱ	−168.170 (16)
C2—C1—N1—C5	0.8 (3)	P1—S1—Co1—N1ⁱ	79.25 (4)
C2—C1—N1—Co1	−174.85 (15)	P1—S1—Co1—N1	−100.75 (4)
C4—C5—N1—C1	−0.8 (3)	P1—S1—Co1—S2ⁱ	168.105 (16)
C4—C5—N1—Co1	174.83 (14)	P1—S1—Co1—S2	−11.895 (16)

Symmetry code: (i) −x+1, −y, −z+2.

(35_Co_DIPY_0m) top

Crystal data top

C₄₆H₅₄CoN₂O₄P₂S₄	F(000) = 994
M_r = 948.06	D_x = 1.277 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7893 reflections
a = 8.0404 (7) Å	θ = 2.5–26.8°
b = 16.3777 (13) Å	µ = 0.62 mm⁻¹
c = 18.9182 (14) Å	T = 296 K
β = 98.074 (4)°	Rectangular, pink
V = 2466.5 (3) Å³	0.12 × 0.09 × 0.06 mm
Z = 2

Data collection top

Bruker APEX-II CCD diffractometer	5402 independent reflections
Radiation source: fine-focus sealed tube	4132 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 27.1°, θ_min = 1.7°
Absorption correction: multi-scan SADABS2014/2 - Bruker AXS area detector scaling and absorption correction	h = −7→10
T_min = 0.637, T_max = 0.746	k = −20→20
21225 measured reflections	l = −24→23

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0609P)² + 0.6454P] where P = (F_o² + 2F_c²)/3
S = 0.93	(Δ/σ)_max = 0.001
5402 reflections	Δρ_max = 0.25 e Å⁻³
274 parameters	Δρ_min = −0.36 e Å⁻³
0 restraints

Crystal data top

C₄₆H₅₄CoN₂O₄P₂S₄	V = 2466.5 (3) Å³
M_r = 948.06	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.0404 (7) Å	µ = 0.62 mm⁻¹
b = 16.3777 (13) Å	T = 296 K
c = 18.9182 (14) Å	0.12 × 0.09 × 0.06 mm
β = 98.074 (4)°

Data collection top

Bruker APEX-II CCD diffractometer	5402 independent reflections
Absorption correction: multi-scan SADABS2014/2 - Bruker AXS area detector scaling and absorption correction	4132 reflections with I > 2σ(I)
T_min = 0.637, T_max = 0.746	R_int = 0.040
21225 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	274 parameters
wR(F²) = 0.106	0 restraints
S = 0.93	Δρ_max = 0.25 e Å⁻³
5402 reflections	Δρ_min = −0.36 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
C1	0.2503 (3)	0.04480 (13)	0.10265 (11)	0.0433 (5)
H1	0.1951	−0.0013	0.0825	0.052*
C2	0.1800 (3)	0.08731 (14)	0.15351 (12)	0.0495 (6)
H2	0.0799	0.0692	0.1674	0.059*
C3	0.2566 (3)	0.15663 (13)	0.18418 (11)	0.0469 (5)
C4	0.4069 (3)	0.18074 (13)	0.16194 (11)	0.0469 (5)
C5	0.4684 (3)	0.13403 (12)	0.11084 (11)	0.0431 (5)
H5	0.5688	0.1504	0.0961	0.052*
C6	0.4989 (4)	0.25683 (17)	0.19054 (16)	0.0797 (9)
H6A	0.4281	0.3036	0.1793	0.120*
H6B	0.5996	0.2629	0.1691	0.120*
H6C	0.5275	0.2524	0.2414	0.120*
C7	0.1786 (4)	0.20383 (18)	0.23916 (16)	0.0770 (9)
H7A	0.1584	0.2590	0.2231	0.115*
H7B	0.2534	0.2039	0.2834	0.115*
H7C	0.0742	0.1788	0.2461	0.115*
C8	0.7740 (3)	−0.04457 (12)	0.24704 (10)	0.0405 (5)
C9	0.7012 (3)	0.01725 (15)	0.28068 (12)	0.0528 (6)
H9	0.5869	0.0277	0.2695	0.063*
C10	0.7992 (4)	0.06408 (16)	0.33150 (13)	0.0668 (7)
C11	0.9682 (4)	0.04688 (18)	0.34614 (14)	0.0701 (8)
H11	1.0348	0.0779	0.3803	0.084*
C12	1.0416 (3)	−0.01482 (18)	0.31178 (14)	0.0636 (7)
C13	0.9416 (3)	−0.06111 (14)	0.26121 (12)	0.0512 (6)
H13	0.9882	−0.1030	0.2372	0.061*
C14	1.2287 (4)	−0.0310 (3)	0.3273 (2)	0.1100 (13)
H14A	1.2616	−0.0665	0.2914	0.165*
H14B	1.2545	−0.0564	0.3733	0.165*
H14C	1.2886	0.0197	0.3271	0.165*
C15	0.7209 (6)	0.1321 (2)	0.3703 (2)	0.1174 (15)
H15A	0.6008	0.1295	0.3591	0.176*
H15B	0.7598	0.1839	0.3556	0.176*
H15C	0.7524	0.1258	0.4209	0.176*
C16	0.8272 (3)	−0.22818 (12)	0.06290 (10)	0.0376 (4)
C17	0.9589 (3)	−0.21200 (14)	0.02679 (12)	0.0470 (5)
H17	1.0280	−0.1673	0.0395	0.056*
C18	0.9893 (3)	−0.26217 (15)	−0.02880 (12)	0.0510 (6)
C19	0.8845 (3)	−0.32820 (15)	−0.04610 (12)	0.0527 (6)
H19	0.9051	−0.3626	−0.0830	0.063*
C20	0.7497 (3)	−0.34467 (13)	−0.01016 (12)	0.0491 (5)
C21	0.7216 (3)	−0.29353 (13)	0.04519 (11)	0.0441 (5)
H21	0.6320	−0.3032	0.0703	0.053*
C22	1.1362 (4)	−0.2456 (2)	−0.06830 (16)	0.0805 (9)
H22A	1.1392	−0.1885	−0.0797	0.121*
H22B	1.1241	−0.2770	−0.1115	0.121*
H22C	1.2386	−0.2606	−0.0388	0.121*
C23	0.6363 (4)	−0.41740 (18)	−0.03058 (17)	0.0823 (9)
H23A	0.5275	−0.4072	−0.0171	0.123*
H23B	0.6840	−0.4652	−0.0063	0.123*
H23C	0.6257	−0.4258	−0.0812	0.123*
N1	0.3945 (2)	0.06700 (10)	0.08091 (8)	0.0371 (4)
O1	0.66587 (19)	−0.09282 (9)	0.19939 (7)	0.0456 (4)
O2	0.80267 (18)	−0.18022 (8)	0.12240 (7)	0.0430 (3)
P1	0.67823 (7)	−0.10299 (3)	0.11610 (3)	0.03504 (14)
S1	0.78101 (7)	−0.00683 (3)	0.07693 (3)	0.04012 (14)
S2	0.54569 (7)	0.13154 (3)	−0.06699 (3)	0.04191 (15)
Co1	0.5000	0.0000	0.0000	0.03209 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0489 (13)	0.0404 (12)	0.0419 (12)	−0.0127 (9)	0.0112 (9)	−0.0099 (9)
C2	0.0523 (14)	0.0512 (13)	0.0489 (13)	−0.0114 (10)	0.0205 (11)	−0.0065 (10)
C3	0.0625 (14)	0.0424 (12)	0.0381 (11)	−0.0025 (10)	0.0154 (10)	−0.0069 (9)
C4	0.0618 (14)	0.0390 (11)	0.0406 (12)	−0.0101 (10)	0.0094 (10)	−0.0103 (9)
C5	0.0441 (12)	0.0403 (11)	0.0467 (12)	−0.0112 (9)	0.0123 (9)	−0.0083 (9)
C6	0.097 (2)	0.0641 (17)	0.084 (2)	−0.0344 (16)	0.0322 (17)	−0.0383 (15)
C7	0.099 (2)	0.0704 (18)	0.0708 (18)	−0.0089 (16)	0.0442 (16)	−0.0254 (15)
C8	0.0503 (13)	0.0430 (12)	0.0280 (10)	−0.0124 (9)	0.0048 (9)	−0.0002 (9)
C9	0.0583 (15)	0.0574 (14)	0.0439 (13)	−0.0049 (11)	0.0114 (11)	−0.0093 (11)
C10	0.093 (2)	0.0604 (16)	0.0483 (14)	−0.0186 (15)	0.0137 (14)	−0.0184 (12)
C11	0.086 (2)	0.0709 (19)	0.0481 (15)	−0.0336 (16)	−0.0094 (14)	−0.0030 (13)
C12	0.0561 (16)	0.0726 (18)	0.0568 (16)	−0.0185 (13)	−0.0108 (12)	0.0170 (14)
C13	0.0542 (15)	0.0487 (13)	0.0497 (13)	−0.0014 (11)	0.0043 (11)	0.0048 (10)
C14	0.061 (2)	0.125 (3)	0.131 (3)	−0.012 (2)	−0.030 (2)	0.025 (3)
C15	0.156 (4)	0.093 (3)	0.107 (3)	−0.007 (2)	0.030 (3)	−0.057 (2)
C16	0.0455 (12)	0.0322 (10)	0.0340 (10)	0.0021 (8)	0.0011 (9)	0.0025 (8)
C17	0.0439 (12)	0.0421 (12)	0.0545 (13)	−0.0088 (10)	0.0046 (10)	−0.0037 (10)
C18	0.0463 (13)	0.0549 (14)	0.0525 (13)	−0.0054 (10)	0.0095 (10)	−0.0044 (11)
C19	0.0615 (15)	0.0484 (13)	0.0490 (14)	−0.0012 (11)	0.0104 (11)	−0.0108 (10)
C20	0.0567 (14)	0.0386 (11)	0.0508 (13)	−0.0089 (10)	0.0038 (11)	−0.0025 (10)
C21	0.0469 (13)	0.0397 (11)	0.0461 (12)	−0.0043 (9)	0.0083 (10)	0.0045 (9)
C22	0.0668 (19)	0.096 (2)	0.086 (2)	−0.0188 (16)	0.0339 (16)	−0.0209 (18)
C23	0.100 (2)	0.0634 (18)	0.086 (2)	−0.0373 (16)	0.0207 (17)	−0.0237 (15)
N1	0.0427 (10)	0.0338 (8)	0.0357 (9)	−0.0077 (7)	0.0089 (7)	−0.0067 (7)
O1	0.0544 (9)	0.0491 (9)	0.0343 (8)	−0.0173 (7)	0.0092 (6)	−0.0065 (6)
O2	0.0528 (9)	0.0401 (8)	0.0341 (7)	0.0034 (6)	−0.0006 (6)	−0.0004 (6)
P1	0.0407 (3)	0.0333 (3)	0.0307 (3)	−0.0064 (2)	0.0034 (2)	−0.0007 (2)
S1	0.0393 (3)	0.0393 (3)	0.0407 (3)	−0.0113 (2)	0.0016 (2)	0.0037 (2)
S2	0.0410 (3)	0.0366 (3)	0.0466 (3)	−0.0111 (2)	0.0007 (2)	−0.0003 (2)
Co1	0.0353 (2)	0.0302 (2)	0.0307 (2)	−0.00491 (14)	0.00447 (15)	−0.00368 (14)

Geometric parameters (Å, º) top

C1—N1	1.334 (3)	C15—H15A	0.9600
C1—C2	1.372 (3)	C15—H15B	0.9600
C1—H1	0.9300	C15—H15C	0.9600
C2—C3	1.380 (3)	C16—C17	1.364 (3)
C2—H2	0.9300	C16—C21	1.378 (3)
C3—C4	1.392 (3)	C16—O2	1.409 (2)
C3—C7	1.502 (3)	C17—C18	1.383 (3)
C4—C5	1.378 (3)	C17—H17	0.9300
C4—C6	1.510 (3)	C18—C19	1.382 (3)
C5—N1	1.336 (2)	C18—C22	1.508 (3)
C5—H5	0.9300	C19—C20	1.385 (3)
C6—H6A	0.9600	C19—H19	0.9300
C6—H6B	0.9600	C20—C21	1.384 (3)
C6—H6C	0.9600	C20—C23	1.517 (3)
C7—H7A	0.9600	C21—H21	0.9300
C7—H7B	0.9600	C22—H22A	0.9600
C7—H7C	0.9600	C22—H22B	0.9600
C8—C13	1.363 (3)	C22—H22C	0.9600
C8—C9	1.370 (3)	C23—H23A	0.9600
C8—O1	1.405 (2)	C23—H23B	0.9600
C9—C10	1.386 (3)	C23—H23C	0.9600
C9—H9	0.9300	N1—Co1	2.1521 (16)
C10—C11	1.377 (4)	O1—P1	1.6013 (15)
C10—C15	1.519 (4)	O2—P1	1.6068 (15)
C11—C12	1.379 (4)	P1—S2ⁱ	1.9629 (7)
C11—H11	0.9300	P1—S1	1.9709 (7)
C12—C13	1.386 (3)	S1—Co1	2.5123 (6)
C12—C14	1.515 (4)	S2—P1ⁱ	1.9630 (7)
C13—H13	0.9300	S2—Co1	2.5520 (5)
C14—H14A	0.9600	Co1—N1ⁱ	2.1522 (16)
C14—H14B	0.9600	Co1—S1ⁱ	2.5123 (6)
C14—H14C	0.9600	Co1—S2ⁱ	2.5521 (5)

N1—C1—C2	122.63 (19)	C17—C16—O2	119.83 (18)
N1—C1—H1	118.7	C21—C16—O2	118.45 (18)
C2—C1—H1	118.7	C16—C17—C18	119.9 (2)
C1—C2—C3	120.6 (2)	C16—C17—H17	120.1
C1—C2—H2	119.7	C18—C17—H17	120.1
C3—C2—H2	119.7	C19—C18—C17	118.6 (2)
C2—C3—C4	117.5 (2)	C19—C18—C22	121.2 (2)
C2—C3—C7	120.6 (2)	C17—C18—C22	120.3 (2)
C4—C3—C7	121.9 (2)	C18—C19—C20	122.0 (2)
C5—C4—C3	117.84 (19)	C18—C19—H19	119.0
C5—C4—C6	120.2 (2)	C20—C19—H19	119.0
C3—C4—C6	121.9 (2)	C21—C20—C19	118.4 (2)
N1—C5—C4	124.86 (19)	C21—C20—C23	120.8 (2)
N1—C5—H5	117.6	C19—C20—C23	120.8 (2)
C4—C5—H5	117.6	C16—C21—C20	119.6 (2)
C4—C6—H6A	109.5	C16—C21—H21	120.2
C4—C6—H6B	109.5	C20—C21—H21	120.2
H6A—C6—H6B	109.5	C18—C22—H22A	109.5
C4—C6—H6C	109.5	C18—C22—H22B	109.5
H6A—C6—H6C	109.5	H22A—C22—H22B	109.5
H6B—C6—H6C	109.5	C18—C22—H22C	109.5
C3—C7—H7A	109.5	H22A—C22—H22C	109.5
C3—C7—H7B	109.5	H22B—C22—H22C	109.5
H7A—C7—H7B	109.5	C20—C23—H23A	109.5
C3—C7—H7C	109.5	C20—C23—H23B	109.5
H7A—C7—H7C	109.5	H23A—C23—H23B	109.5
H7B—C7—H7C	109.5	C20—C23—H23C	109.5
C13—C8—C9	122.0 (2)	H23A—C23—H23C	109.5
C13—C8—O1	121.3 (2)	H23B—C23—H23C	109.5
C9—C8—O1	116.6 (2)	C1—N1—C5	116.58 (17)
C8—C9—C10	119.5 (2)	C1—N1—Co1	121.80 (13)
C8—C9—H9	120.2	C5—N1—Co1	121.61 (13)
C10—C9—H9	120.2	C8—O1—P1	124.87 (13)
C11—C10—C9	118.4 (3)	C16—O2—P1	122.36 (12)
C11—C10—C15	121.1 (3)	O1—P1—O2	97.64 (8)
C9—C10—C15	120.5 (3)	O1—P1—S2ⁱ	108.12 (6)
C10—C11—C12	122.1 (2)	O2—P1—S2ⁱ	111.58 (6)
C10—C11—H11	119.0	O1—P1—S1	111.97 (6)
C12—C11—H11	119.0	O2—P1—S1	111.55 (6)
C11—C12—C13	118.7 (3)	S2ⁱ—P1—S1	114.68 (3)
C11—C12—C14	121.1 (3)	P1—S1—Co1	82.12 (2)
C13—C12—C14	120.2 (3)	P1ⁱ—S2—Co1	81.23 (2)
C8—C13—C12	119.3 (2)	N1—Co1—N1ⁱ	180.00 (5)
C8—C13—H13	120.4	N1—Co1—S1ⁱ	88.68 (5)
C12—C13—H13	120.4	N1ⁱ—Co1—S1ⁱ	91.32 (5)
C12—C14—H14A	109.5	N1—Co1—S1	91.32 (5)
C12—C14—H14B	109.5	N1ⁱ—Co1—S1	88.68 (5)
H14A—C14—H14B	109.5	S1ⁱ—Co1—S1	180.0
C12—C14—H14C	109.5	N1—Co1—S2	91.23 (4)
H14A—C14—H14C	109.5	N1ⁱ—Co1—S2	88.77 (4)
H14B—C14—H14C	109.5	S1ⁱ—Co1—S2	81.673 (16)
C10—C15—H15A	109.5	S1—Co1—S2	98.326 (16)
C10—C15—H15B	109.5	N1—Co1—S2ⁱ	88.77 (4)
H15A—C15—H15B	109.5	N1ⁱ—Co1—S2ⁱ	91.23 (4)
C10—C15—H15C	109.5	S1ⁱ—Co1—S2ⁱ	98.328 (16)
H15A—C15—H15C	109.5	S1—Co1—S2ⁱ	81.673 (16)
H15B—C15—H15C	109.5	S2—Co1—S2ⁱ	180.0
C17—C16—C21	121.62 (19)

N1—C1—C2—C3	0.7 (4)	C2—C1—N1—C5	−0.6 (3)
C1—C2—C3—C4	−0.5 (4)	C2—C1—N1—Co1	−179.18 (17)
C1—C2—C3—C7	179.2 (2)	C4—C5—N1—C1	0.2 (3)
C2—C3—C4—C5	0.2 (3)	C4—C5—N1—Co1	178.85 (17)
C7—C3—C4—C5	−179.5 (2)	C13—C8—O1—P1	−62.8 (3)
C2—C3—C4—C6	178.4 (2)	C9—C8—O1—P1	120.08 (19)
C7—C3—C4—C6	−1.3 (4)	C17—C16—O2—P1	94.9 (2)
C3—C4—C5—N1	−0.1 (4)	C21—C16—O2—P1	−88.6 (2)
C6—C4—C5—N1	−178.3 (2)	C8—O1—P1—O2	89.74 (17)
C13—C8—C9—C10	−0.9 (4)	C8—O1—P1—S2ⁱ	−154.51 (15)
O1—C8—C9—C10	176.2 (2)	C8—O1—P1—S1	−27.24 (18)
C8—C9—C10—C11	0.4 (4)	C16—O2—P1—O1	164.80 (15)
C8—C9—C10—C15	−179.1 (3)	C16—O2—P1—S2ⁱ	51.81 (16)
C9—C10—C11—C12	0.2 (4)	C16—O2—P1—S1	−77.89 (15)
C15—C10—C11—C12	179.7 (3)	O1—P1—S1—Co1	−118.73 (7)
C10—C11—C12—C13	−0.3 (4)	O2—P1—S1—Co1	133.00 (6)
C10—C11—C12—C14	178.2 (3)	S2ⁱ—P1—S1—Co1	4.93 (3)
C9—C8—C13—C12	0.8 (3)	C1—N1—Co1—S1ⁱ	49.93 (16)
O1—C8—C13—C12	−176.2 (2)	C5—N1—Co1—S1ⁱ	−128.62 (16)
C11—C12—C13—C8	−0.2 (4)	C1—N1—Co1—S1	−130.07 (16)
C14—C12—C13—C8	−178.7 (2)	C5—N1—Co1—S1	51.38 (16)
C21—C16—C17—C18	−0.4 (3)	C1—N1—Co1—S2	131.57 (16)
O2—C16—C17—C18	175.94 (19)	C5—N1—Co1—S2	−46.98 (16)
C16—C17—C18—C19	−0.3 (4)	C1—N1—Co1—S2ⁱ	−48.43 (16)
C16—C17—C18—C22	−179.0 (2)	C5—N1—Co1—S2ⁱ	133.02 (16)
C17—C18—C19—C20	0.9 (4)	P1—S1—Co1—N1	85.08 (5)
C22—C18—C19—C20	179.6 (3)	P1—S1—Co1—N1ⁱ	−94.92 (5)
C18—C19—C20—C21	−0.8 (4)	P1—S1—Co1—S2	176.52 (2)
C18—C19—C20—C23	179.7 (3)	P1—S1—Co1—S2ⁱ	−3.48 (2)
C17—C16—C21—C20	0.5 (3)	P1ⁱ—S2—Co1—N1	−91.99 (5)
O2—C16—C21—C20	−175.89 (19)	P1ⁱ—S2—Co1—N1ⁱ	88.01 (5)
C19—C20—C21—C16	0.1 (3)	P1ⁱ—S2—Co1—S1ⁱ	−3.51 (2)
C23—C20—C21—C16	179.6 (2)	P1ⁱ—S2—Co1—S1	176.49 (2)

Symmetry code: (i) −x+1, −y, −z.

(35_Co_ETPY_0m) top

Crystal data top

C₄₆H₅₄CoN₂O₄P₂S₄	Z = 1
M_r = 948.06	F(000) = 497
Triclinic, P1	D_x = 1.332 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5631 (7) Å	Cell parameters from 5679 reflections
b = 9.8309 (6) Å	θ = 2.3–25.7°
c = 14.2326 (9) Å	µ = 0.65 mm⁻¹
α = 99.290 (3)°	T = 296 K
β = 98.602 (3)°	Rectangular, pink
γ = 112.994 (3)°	0.12 × 0.09 × 0.06 mm
V = 1181.83 (14) Å³

Data collection top

Radiation source: fine-focus sealed tube	3991 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Absorption correction: multi-scan SADABS2014/2 - Bruker AXS area detector scaling and absorption correction	θ_max = 27.2°, θ_min = 1.5°
T_min = 0.650, T_max = 0.746	h = −12→11
24294 measured reflections	k = −12→12
5258 independent reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0397P)² + 0.2495P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
5258 reflections	Δρ_max = 0.33 e Å⁻³
273 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints

Crystal data top

C₄₆H₅₄CoN₂O₄P₂S₄	γ = 112.994 (3)°
M_r = 948.06	V = 1181.83 (14) Å³
Triclinic, P1	Z = 1
a = 9.5631 (7) Å	Mo Kα radiation
b = 9.8309 (6) Å	µ = 0.65 mm⁻¹
c = 14.2326 (9) Å	T = 296 K
α = 99.290 (3)°	0.12 × 0.09 × 0.06 mm
β = 98.602 (3)°

Data collection top

Absorption correction: multi-scan SADABS2014/2 - Bruker AXS area detector scaling and absorption correction	5258 independent reflections
T_min = 0.650, T_max = 0.746	3991 reflections with I > 2σ(I)
24294 measured reflections	R_int = 0.042

Refinement top

R[F² > 2σ(F²)] = 0.036	273 parameters
wR(F²) = 0.092	0 restraints
S = 1.04	Δρ_max = 0.33 e Å⁻³
5258 reflections	Δρ_min = −0.23 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
C1	0.2565 (2)	0.9175 (2)	0.93807 (15)	0.0375 (5)
H1	0.3101	1.0230	0.9522	0.045*
C2	0.3336 (3)	0.8316 (2)	0.90884 (15)	0.0396 (5)
H2	0.4367	0.8793	0.9042	0.047*
C3	0.2575 (3)	0.6743 (2)	0.88627 (16)	0.0417 (5)
C4	0.1039 (3)	0.6124 (2)	0.89462 (18)	0.0485 (6)
H4	0.0473	0.5072	0.8800	0.058*
C5	0.0351 (3)	0.7056 (2)	0.92433 (17)	0.0435 (5)
H5	−0.0684	0.6606	0.9288	0.052*
C6	0.3373 (3)	0.5747 (3)	0.8552 (2)	0.0582 (7)
H6A	0.4473	0.6387	0.8626	0.070*
H6B	0.3297	0.5066	0.8984	0.070*
C7	0.2692 (4)	0.4818 (3)	0.7514 (2)	0.0730 (9)
H7A	0.1604	0.4180	0.7434	0.110*
H7B	0.3230	0.4195	0.7365	0.110*
H7C	0.2807	0.5485	0.7079	0.110*
C8	−0.2096 (3)	1.1765 (2)	0.72296 (16)	0.0413 (5)
C9	−0.1775 (3)	1.2691 (2)	0.65879 (17)	0.0486 (6)
H9	−0.1249	1.2534	0.6112	0.058*
C10	−0.2249 (3)	1.3868 (3)	0.6662 (2)	0.0587 (7)
C11	−0.3055 (3)	1.4047 (3)	0.7367 (2)	0.0632 (8)
H11	−0.3369	1.4835	0.7421	0.076*
C12	−0.3407 (3)	1.3093 (3)	0.79913 (19)	0.0599 (7)
C13	−0.2894 (3)	1.1949 (3)	0.79320 (18)	0.0510 (6)
H13	−0.3088	1.1314	0.8362	0.061*
C14	−0.4379 (5)	1.3260 (5)	0.8709 (2)	0.1085 (14)
H14A	−0.4136	1.4317	0.8941	0.163*
H14B	−0.4150	1.2855	0.9253	0.163*
H14C	−0.5467	1.2712	0.8390	0.163*
C15	−0.1878 (5)	1.4939 (3)	0.5980 (3)	0.0972 (12)
H15A	−0.2813	1.4706	0.5503	0.146*
H15B	−0.1112	1.4813	0.5654	0.146*
H15C	−0.1475	1.5972	0.6354	0.146*
C16	0.0980 (3)	0.9486 (2)	0.67280 (14)	0.0369 (5)
C17	0.1929 (3)	0.8739 (2)	0.67599 (15)	0.0401 (5)
H17	0.1725	0.7942	0.7071	0.048*
C18	0.3195 (3)	0.9173 (3)	0.63267 (16)	0.0455 (5)
C19	0.3460 (3)	1.0362 (3)	0.58696 (16)	0.0476 (6)
H19	0.4315	1.0673	0.5588	0.057*
C20	0.2492 (3)	1.1099 (2)	0.58185 (15)	0.0445 (5)
C21	0.1234 (3)	1.0646 (2)	0.62509 (16)	0.0442 (5)
H21	0.0562	1.1122	0.6220	0.053*
C22	0.4261 (3)	0.8373 (3)	0.6363 (2)	0.0663 (7)
H22A	0.5131	0.8888	0.6096	0.099*
H22B	0.3693	0.7338	0.5986	0.099*
H22C	0.4634	0.8383	0.7030	0.099*
C23	0.2787 (4)	1.2362 (3)	0.52887 (19)	0.0626 (7)
H23A	0.2002	1.2736	0.5320	0.094*
H23B	0.2749	1.1977	0.4616	0.094*
H23C	0.3799	1.3175	0.5593	0.094*
N1	0.1091 (2)	0.85802 (18)	0.94729 (12)	0.0349 (4)
S1	−0.09726 (6)	0.83156 (6)	1.11663 (4)	0.03892 (14)
S2	−0.22936 (6)	0.86021 (6)	0.85104 (4)	0.03851 (14)
O1	−0.16621 (18)	1.05524 (16)	0.70770 (10)	0.0432 (4)
O2	−0.02978 (18)	0.89432 (15)	0.71634 (10)	0.0408 (4)
P1	−0.08148 (6)	0.99841 (6)	0.78859 (4)	0.03383 (14)
Co1	0.0000	1.0000	1.0000	0.03154 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0343 (12)	0.0313 (10)	0.0462 (12)	0.0140 (9)	0.0074 (10)	0.0086 (9)
C2	0.0298 (12)	0.0405 (11)	0.0477 (12)	0.0152 (10)	0.0093 (10)	0.0078 (10)
C3	0.0387 (13)	0.0412 (12)	0.0483 (13)	0.0229 (10)	0.0076 (10)	0.0060 (10)
C4	0.0436 (14)	0.0287 (10)	0.0705 (16)	0.0149 (10)	0.0133 (12)	0.0057 (10)
C5	0.0342 (12)	0.0337 (11)	0.0628 (14)	0.0143 (10)	0.0143 (11)	0.0097 (10)
C6	0.0468 (15)	0.0448 (13)	0.0846 (19)	0.0263 (12)	0.0149 (14)	0.0024 (13)
C7	0.103 (3)	0.0644 (17)	0.0710 (18)	0.0524 (18)	0.0314 (17)	0.0126 (14)
C8	0.0415 (13)	0.0397 (11)	0.0445 (12)	0.0221 (10)	0.0009 (10)	0.0112 (10)
C9	0.0444 (14)	0.0448 (12)	0.0519 (14)	0.0146 (11)	0.0045 (11)	0.0173 (11)
C10	0.0576 (17)	0.0380 (12)	0.0676 (17)	0.0129 (12)	−0.0083 (14)	0.0187 (12)
C11	0.073 (2)	0.0455 (14)	0.0694 (18)	0.0366 (14)	−0.0116 (15)	0.0052 (13)
C12	0.0674 (19)	0.0688 (17)	0.0567 (15)	0.0493 (15)	0.0020 (13)	0.0094 (13)
C13	0.0605 (17)	0.0587 (14)	0.0528 (14)	0.0404 (13)	0.0154 (12)	0.0225 (12)
C14	0.147 (4)	0.164 (4)	0.090 (2)	0.134 (3)	0.044 (2)	0.041 (2)
C15	0.120 (3)	0.0575 (18)	0.110 (3)	0.0272 (19)	0.012 (2)	0.0491 (18)
C16	0.0383 (12)	0.0384 (11)	0.0334 (11)	0.0167 (10)	0.0099 (9)	0.0048 (9)
C17	0.0471 (14)	0.0399 (11)	0.0375 (11)	0.0220 (10)	0.0110 (10)	0.0105 (9)
C18	0.0446 (14)	0.0514 (13)	0.0435 (12)	0.0245 (11)	0.0119 (11)	0.0074 (11)
C19	0.0488 (15)	0.0542 (14)	0.0425 (13)	0.0210 (12)	0.0210 (11)	0.0114 (11)
C20	0.0556 (15)	0.0433 (12)	0.0336 (11)	0.0189 (11)	0.0141 (11)	0.0087 (9)
C21	0.0561 (15)	0.0438 (12)	0.0434 (12)	0.0296 (12)	0.0159 (11)	0.0132 (10)
C22	0.0605 (18)	0.0752 (18)	0.0841 (19)	0.0424 (16)	0.0304 (16)	0.0272 (15)
C23	0.081 (2)	0.0590 (15)	0.0587 (16)	0.0308 (15)	0.0318 (15)	0.0266 (13)
N1	0.0337 (10)	0.0312 (8)	0.0427 (10)	0.0158 (8)	0.0099 (8)	0.0105 (7)
S1	0.0370 (3)	0.0332 (3)	0.0464 (3)	0.0125 (2)	0.0115 (2)	0.0141 (2)
S2	0.0322 (3)	0.0375 (3)	0.0462 (3)	0.0132 (2)	0.0113 (2)	0.0131 (2)
O1	0.0514 (10)	0.0488 (8)	0.0415 (8)	0.0324 (8)	0.0106 (7)	0.0145 (7)
O2	0.0444 (9)	0.0364 (7)	0.0491 (9)	0.0211 (7)	0.0201 (7)	0.0121 (7)
P1	0.0351 (3)	0.0342 (3)	0.0390 (3)	0.0194 (2)	0.0116 (2)	0.0124 (2)
Co1	0.0307 (2)	0.0294 (2)	0.0393 (2)	0.01599 (17)	0.01016 (17)	0.01074 (16)

Geometric parameters (Å, º) top

C1—N1	1.335 (3)	C15—H15A	0.9600
C1—C2	1.376 (3)	C15—H15B	0.9600
C1—H1	0.9300	C15—H15C	0.9600
C2—C3	1.384 (3)	C16—C17	1.372 (3)
C2—H2	0.9300	C16—C21	1.380 (3)
C3—C4	1.385 (3)	C16—O2	1.409 (2)
C3—C6	1.510 (3)	C17—C18	1.391 (3)
C4—C5	1.372 (3)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.384 (3)
C5—N1	1.341 (2)	C18—C22	1.511 (3)
C5—H5	0.9300	C19—C20	1.381 (3)
C6—C7	1.501 (4)	C19—H19	0.9300
C6—H6A	0.9700	C20—C21	1.384 (3)
C6—H6B	0.9700	C20—C23	1.511 (3)
C7—H7A	0.9600	C21—H21	0.9300
C7—H7B	0.9600	C22—H22A	0.9600
C7—H7C	0.9600	C22—H22B	0.9600
C8—C9	1.375 (3)	C22—H22C	0.9600
C8—C13	1.376 (3)	C23—H23A	0.9600
C8—O1	1.404 (2)	C23—H23B	0.9600
C9—C10	1.393 (3)	C23—H23C	0.9600
C9—H9	0.9300	N1—Co1	2.1523 (16)
C10—C11	1.383 (4)	S1—P1ⁱ	1.9712 (8)
C10—C15	1.521 (4)	S1—Co1	2.5512 (5)
C11—C12	1.376 (4)	S2—P1	1.9750 (8)
C11—H11	0.9300	S2—Co1	2.5510 (6)
C12—C13	1.388 (3)	O1—P1	1.6051 (15)
C12—C14	1.511 (4)	O2—P1	1.5989 (14)
C13—H13	0.9300	P1—S1ⁱ	1.9712 (8)
C14—H14A	0.9600	Co1—N1ⁱ	2.1523 (16)
C14—H14B	0.9600	Co1—S2ⁱ	2.5510 (6)
C14—H14C	0.9600	Co1—S1ⁱ	2.5512 (5)

N1—C1—C2	123.73 (19)	C17—C16—O2	116.03 (18)
N1—C1—H1	118.1	C21—C16—O2	122.65 (19)
C2—C1—H1	118.1	C16—C17—C18	119.9 (2)
C1—C2—C3	120.0 (2)	C16—C17—H17	120.0
C1—C2—H2	120.0	C18—C17—H17	120.0
C3—C2—H2	120.0	C19—C18—C17	118.3 (2)
C2—C3—C4	116.34 (19)	C19—C18—C22	121.0 (2)
C2—C3—C6	122.1 (2)	C17—C18—C22	120.6 (2)
C4—C3—C6	121.53 (19)	C20—C19—C18	122.0 (2)
C5—C4—C3	120.28 (19)	C20—C19—H19	119.0
C5—C4—H4	119.9	C18—C19—H19	119.0
C3—C4—H4	119.9	C19—C20—C21	118.8 (2)
N1—C5—C4	123.5 (2)	C19—C20—C23	120.6 (2)
N1—C5—H5	118.3	C21—C20—C23	120.5 (2)
C4—C5—H5	118.3	C16—C21—C20	119.6 (2)
C7—C6—C3	113.4 (2)	C16—C21—H21	120.2
C7—C6—H6A	108.9	C20—C21—H21	120.2
C3—C6—H6A	108.9	C18—C22—H22A	109.5
C7—C6—H6B	108.9	C18—C22—H22B	109.5
C3—C6—H6B	108.9	H22A—C22—H22B	109.5
H6A—C6—H6B	107.7	C18—C22—H22C	109.5
C6—C7—H7A	109.5	H22A—C22—H22C	109.5
C6—C7—H7B	109.5	H22B—C22—H22C	109.5
H7A—C7—H7B	109.5	C20—C23—H23A	109.5
C6—C7—H7C	109.5	C20—C23—H23B	109.5
H7A—C7—H7C	109.5	H23A—C23—H23B	109.5
H7B—C7—H7C	109.5	C20—C23—H23C	109.5
C9—C8—C13	122.0 (2)	H23A—C23—H23C	109.5
C9—C8—O1	115.8 (2)	H23B—C23—H23C	109.5
C13—C8—O1	122.0 (2)	C1—N1—C5	116.18 (17)
C8—C9—C10	119.0 (2)	C1—N1—Co1	121.54 (13)
C8—C9—H9	120.5	C5—N1—Co1	122.26 (14)
C10—C9—H9	120.5	P1ⁱ—S1—Co1	81.66 (2)
C11—C10—C9	118.8 (2)	P1—S2—Co1	81.59 (2)
C11—C10—C15	120.8 (3)	C8—O1—P1	127.68 (13)
C9—C10—C15	120.4 (3)	C16—O2—P1	125.27 (12)
C12—C11—C10	121.9 (2)	O2—P1—O1	98.00 (8)
C12—C11—H11	119.0	O2—P1—S1ⁱ	112.95 (6)
C10—C11—H11	119.0	O1—P1—S1ⁱ	112.31 (6)
C11—C12—C13	119.0 (3)	O2—P1—S2	106.33 (6)
C11—C12—C14	120.5 (2)	O1—P1—S2	112.76 (7)
C13—C12—C14	120.5 (3)	S1ⁱ—P1—S2	113.37 (4)
C8—C13—C12	119.2 (2)	N1ⁱ—Co1—N1	179.999 (1)
C8—C13—H13	120.4	N1ⁱ—Co1—S2	90.26 (5)
C12—C13—H13	120.4	N1—Co1—S2	89.74 (5)
C12—C14—H14A	109.5	N1ⁱ—Co1—S2ⁱ	89.74 (5)
C12—C14—H14B	109.5	N1—Co1—S2ⁱ	90.26 (5)
H14A—C14—H14B	109.5	S2—Co1—S2ⁱ	180.0
C12—C14—H14C	109.5	N1ⁱ—Co1—S1ⁱ	89.23 (5)
H14A—C14—H14C	109.5	N1—Co1—S1ⁱ	90.77 (5)
H14B—C14—H14C	109.5	S2—Co1—S1ⁱ	80.532 (18)
C10—C15—H15A	109.5	S2ⁱ—Co1—S1ⁱ	99.467 (18)
C10—C15—H15B	109.5	N1ⁱ—Co1—S1	90.77 (5)
H15A—C15—H15B	109.5	N1—Co1—S1	89.23 (5)
C10—C15—H15C	109.5	S2—Co1—S1	99.468 (19)
H15A—C15—H15C	109.5	S2ⁱ—Co1—S1	80.533 (18)
H15B—C15—H15C	109.5	S1ⁱ—Co1—S1	179.999 (1)
C17—C16—C21	121.2 (2)

N1—C1—C2—C3	0.6 (3)	C2—C1—N1—Co1	177.05 (16)
C1—C2—C3—C4	0.3 (3)	C4—C5—N1—C1	1.2 (3)
C1—C2—C3—C6	−179.1 (2)	C4—C5—N1—Co1	−177.11 (18)
C2—C3—C4—C5	−0.3 (3)	C9—C8—O1—P1	136.37 (18)
C6—C3—C4—C5	179.1 (2)	C13—C8—O1—P1	−48.2 (3)
C3—C4—C5—N1	−0.4 (4)	C17—C16—O2—P1	134.26 (16)
C2—C3—C6—C7	−114.2 (3)	C21—C16—O2—P1	−49.0 (3)
C4—C3—C6—C7	66.5 (3)	C16—O2—P1—O1	77.52 (17)
C13—C8—C9—C10	1.1 (4)	C16—O2—P1—S1ⁱ	−40.90 (17)
O1—C8—C9—C10	176.57 (19)	C16—O2—P1—S2	−165.85 (14)
C8—C9—C10—C11	−1.3 (4)	C8—O1—P1—O2	−165.06 (17)
C8—C9—C10—C15	178.5 (2)	C8—O1—P1—S1ⁱ	−46.16 (19)
C9—C10—C11—C12	−0.3 (4)	C8—O1—P1—S2	83.42 (18)
C15—C10—C11—C12	179.9 (3)	Co1—S2—P1—O2	109.61 (6)
C10—C11—C12—C13	2.1 (4)	Co1—S2—P1—O1	−144.12 (6)
C10—C11—C12—C14	−176.1 (3)	Co1—S2—P1—S1ⁱ	−15.09 (3)
C9—C8—C13—C12	0.7 (4)	C1—N1—Co1—S2	128.14 (16)
O1—C8—C13—C12	−174.5 (2)	C5—N1—Co1—S2	−53.64 (16)
C11—C12—C13—C8	−2.2 (4)	C1—N1—Co1—S2ⁱ	−51.86 (16)
C14—C12—C13—C8	175.9 (3)	C5—N1—Co1—S2ⁱ	126.36 (16)
C21—C16—C17—C18	1.6 (3)	C1—N1—Co1—S1ⁱ	47.61 (16)
O2—C16—C17—C18	178.40 (18)	C5—N1—Co1—S1ⁱ	−134.16 (16)
C16—C17—C18—C19	−0.1 (3)	C1—N1—Co1—S1	−132.39 (16)
C16—C17—C18—C22	179.4 (2)	C5—N1—Co1—S1	45.84 (16)
C17—C18—C19—C20	−1.2 (3)	P1—S2—Co1—N1ⁱ	99.96 (5)
C22—C18—C19—C20	179.3 (2)	P1—S2—Co1—N1	−80.04 (5)
C18—C19—C20—C21	1.0 (3)	P1—S2—Co1—S1ⁱ	10.79 (2)
C18—C19—C20—C23	−178.2 (2)	P1—S2—Co1—S1	−169.21 (2)
C17—C16—C21—C20	−1.8 (3)	P1ⁱ—S1—Co1—N1ⁱ	−78.80 (5)
O2—C16—C21—C20	−178.43 (18)	P1ⁱ—S1—Co1—N1	101.20 (5)
C19—C20—C21—C16	0.6 (3)	P1ⁱ—S1—Co1—S2	−169.19 (2)
C23—C20—C21—C16	179.7 (2)	P1ⁱ—S1—Co1—S2ⁱ	10.81 (2)
C2—C1—N1—C5	−1.3 (3)

Symmetry code: (i) −x, −y+2, −z+2.

Experimental details

	(24COETPY_0m)	(35Co_jammu_0m)	(35_Co_DIPY_0m)	(35_Co_ETPY_0m)
Crystal data
Chemical formula	C₄₆H₅₄CoN₂O₄P₂S₄	C₄₂H₄₆CoN₂O₄P₂S₄	C₄₆H₅₄CoN₂O₄P₂S₄	C₄₆H₅₄CoN₂O₄P₂S₄
M_r	948.06	891.96	948.06	948.06
Crystal system, space group	Monoclinic, P2₁/n	Monoclinic, P2₁/n	Monoclinic, P2₁/c	Triclinic, P1
Temperature (K)	296	296	296	296
a, b, c (Å)	10.254 (3), 15.557 (5), 15.444 (6)	11.8107 (6), 14.4211 (9), 12.8807 (7)	8.0404 (7), 16.3777 (13), 18.9182 (14)	9.5631 (7), 9.8309 (6), 14.2326 (9)
α, β, γ (°)	90, 102.287 (5), 90	90, 104.929 (2), 90	90, 98.074 (4), 90	99.290 (3), 98.602 (3), 112.994 (3)
V (Å³)	2407.2 (14)	2119.8 (2)	2466.5 (3)	1181.83 (14)
Z	2	2	2	1
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.64	0.72	0.62	0.65
Crystal size (mm)	0.15 × 0.12 × 0.08	0.10 × 0.07 × 0.05	0.12 × 0.09 × 0.06	0.12 × 0.09 × 0.06

Data collection
Diffractometer	Bruker APEX-II CCD diffractometer	Bruker APEX-II CCD diffractometer	Bruker APEX-II CCD diffractometer	?
Absorption correction	Multi-scan SADABS2014/2 - Bruker AXS area detector scaling and absorption correction	Multi-scan SADABS2008/1 - Bruker AXS area detector scaling and absorption correction	Multi-scan SADABS2014/2 - Bruker AXS area detector scaling and absorption correction	Multi-scan SADABS2014/2 - Bruker AXS area detector scaling and absorption correction
T_min, T_max	0.626, 0.746	0.648, 0.746	0.637, 0.746	0.650, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	19203, 5308, 3263	22789, 6024, 5025	21225, 5402, 4132	24294, 5258, 3991
R_int	0.066	0.020	0.040	0.042
(sin θ/λ)_max (Å⁻¹)	0.649	0.701	0.640	0.643

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.256, 1.00	0.030, 0.087, 1.03	0.036, 0.106, 0.93	0.036, 0.092, 1.04
No. of reflections	5308	6024	5402	5258
No. of parameters	273	254	274	273
No. of restraints	1	0	0	0
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.58	0.31, −0.28	0.25, −0.36	0.33, −0.23

Computer programs: Bruker APEX2, Bruker SAINT, Sir-92 (Altomare et al., 1993), Sir-92 (Sheldrick, 1993), SHELXL2014 (Sheldrick 2014), SHELXL97 (Sheldrick, 2008), Bruker SHELXTL.

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