Cobalt(II) chloride adducts with aceto­nitrile, propan-2-ol and tetra­hydro­furan: considerations on nuclearity, reactivity and synthetic applications

High-spin cobalt(II) complexes are considered useful building blocks for the synthesis of single-mol­ecule magnets (SMM) because of their intrinsic magnetic anisotropy. In this work, three new cobalt(II) chloride adducts with labile ligands have been synthesized from anhydrous CoCl₂, to be subsequently employed as starting materials for heterobimetallic compounds. The products were characterized by elemental, spectroscopic (EPR and FT–IR) and single-crystal X-ray diffraction analyses. trans-Tetra­kis(aceto­nitrile-κN)bis­(tetra­hydro­furan-κO)cobalt(II) bis­[(aceto­nitrile-κN)tri­chlorido­co­baltate(II)], [Co(C₂H₃N)₄(C₄H₈O)₂][CoCl₃(C₂H₃N)]₂, (1), comprises mononuclear ions and contains both aceto­nitrile and tetra­hydro­furan (thf) ligands, The coordination polymer catena-poly[[tetra­kis­(propan-2-ol-κO)cobalt(II)]-μ-chlorido-[di­chlorido­cobalt(II)]-μ-chlorido], [Co₂Cl₄(C₃H₈O)₄], (2′), was prepared by direct reaction between anhydrous CoCl₂ and propan-2-ol in an attempt to rationalize the formation of the CoCl₂–alcohol adduct (2), probably CoCl₂(HOⁱPr)_m. The binuclear complex di-μ-chlorido-1:2κ⁴Cl:Cl-di­chlorido-2κ²Cl-tetra­kis­(tetra­hydro­furan-1κO)dicobalt(II), [Co₂Cl₄(C₄H₈O)₄], (3), was obtained from (2) after recrystallization from tetra­hydro­furan. All three products present cobalt(II) centres in both octa­hedral and tetra­hedral environments, the former usually less distorted than the latter, regardless of the nature of the neutral ligand. Product (2′) is stabilized by an intra­molecular hydrogen-bond network that appears to favour a trans arrangement of the chloride ligands in the octa­hedral moiety; this differs from the cis disposition found in (3). The expected easy displacement of the bound solvent mol­ecules from the metal coordination sphere makes the three compounds good candidates for suitable starting materials in a number of synthetic applications.

Computing details

For all compounds, data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP (Johnson, 1976) and ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) and WinGX (Farrugia, 2012).

(compound-1) Tetrakis(acetonitrile-κN)bis(tetrahydrofuran-κO)cobalt(II) bis[(acetonitrile-κN)trichloridocobaltate(II)]

Crystal data

[Co(C2H3N)4(C4H8O)2]·2[CoCl3(C2H3N)]	Z = 1
Mr = 780.02	F(000) = 395
Triclinic, P1	Dx = 1.547 Mg m^−3
a = 7.7669 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1516 (6) Å	Cell parameters from 9949 reflections
c = 12.4114 (9) Å	θ = 2.7–28.4°
α = 99.665 (3)°	µ = 1.98 mm^−1
β = 104.290 (3)°	T = 100 K
γ = 93.968 (3)°	Block, translucent intense blue
V = 837.09 (11) Å^3	0.20 × 0.15 × 0.10 mm

Data collection

Bruker D8 Venture/Photon 100 CMOS diffractometer	3836 independent reflections
Radiation source: fine-focus sealed tube	3389 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 10.4167 pixels mm^-1	θmax = 27.5°, θmin = 3.6°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −11→11
Tmin = 0.674, Tmax = 0.746	l = −16→16
43965 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.053	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0242P)^2 + 0.4147P] where P = (Fo^2 + 2Fc^2)/3
3836 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Co1	0.5000	0.0000	0.5000	0.01311 (6)
O1	0.64865 (14)	0.08899 (11)	0.66575 (8)	0.0191 (2)
C10A	0.7311 (3)	0.0011 (2)	0.74676 (16)	0.0485 (6)	0.374 (14)
H10A	0.6482	−0.0883	0.7420	0.058*	0.374 (14)
H10B	0.8415	−0.0324	0.7296	0.058*	0.374 (14)
C11A	0.7731 (15)	0.0898 (8)	0.8578 (6)	0.0323 (17)	0.374 (14)
H11A	0.8950	0.0775	0.9010	0.039*	0.374 (14)
H11B	0.6868	0.0601	0.8993	0.039*	0.374 (14)
C12A	0.7619 (2)	0.2510 (2)	0.84281 (15)	0.0333 (4)	0.374 (14)
H12A	0.7114	0.3073	0.9008	0.040*	0.374 (14)
H12B	0.8813	0.3015	0.8481	0.040*	0.374 (14)
C10B	0.7311 (3)	0.0011 (2)	0.74676 (16)	0.0485 (6)	0.626 (14)
H10C	0.8044	−0.0690	0.7139	0.058*	0.626 (14)
H10D	0.6391	−0.0566	0.7705	0.058*	0.626 (14)
C11B	0.8468 (10)	0.1131 (6)	0.8458 (4)	0.0402 (14)	0.626 (14)
H11C	0.8512	0.0788	0.9179	0.048*	0.626 (14)
H11D	0.9702	0.1285	0.8379	0.048*	0.626 (14)
C12B	0.7619 (2)	0.2510 (2)	0.84281 (15)	0.0333 (4)	0.626 (14)
H12C	0.8539	0.3379	0.8595	0.040*	0.626 (14)
H12D	0.6927	0.2647	0.9002	0.040*	0.626 (14)
C13	0.6404 (2)	0.23802 (17)	0.72689 (14)	0.0299 (4)
H13A	0.5165	0.2507	0.7311	0.036*
H13B	0.6807	0.3151	0.6884	0.036*
N2	0.27441 (16)	0.09127 (13)	0.53524 (11)	0.0203 (3)
C20	0.1641 (2)	0.15372 (16)	0.55918 (14)	0.0239 (3)
C21	0.0256 (2)	0.2359 (2)	0.5910 (2)	0.0417 (5)
H21A	0.0739	0.2981	0.6665	0.063*
H21B	−0.0748	0.1656	0.5921	0.063*
H21C	−0.0160	0.2995	0.5360	0.063*
N3	0.43478 (16)	−0.20076 (13)	0.54904 (10)	0.0192 (2)
C30	0.4175 (2)	−0.30187 (16)	0.58893 (12)	0.0196 (3)
C31	0.3969 (3)	−0.42980 (18)	0.64161 (14)	0.0307 (4)
H31A	0.4514	−0.4016	0.7234	0.046*	0.59 (2)
H31B	0.4561	−0.5108	0.6093	0.046*	0.59 (2)
H31C	0.2695	−0.4633	0.6278	0.046*	0.59 (2)
H31D	0.3332	−0.5156	0.5836	0.046*	0.41 (2)
H31E	0.3286	−0.4063	0.6977	0.046*	0.41 (2)
H31F	0.5152	−0.4539	0.6792	0.046*	0.41 (2)
Co2	0.03936 (3)	0.67240 (2)	0.79974 (2)	0.01989 (6)
Cl3	0.20716 (5)	0.50053 (4)	0.86682 (3)	0.02761 (9)
Cl4	−0.14454 (6)	0.58426 (5)	0.62702 (3)	0.03506 (11)
Cl5A	0.2084 (6)	0.8824 (4)	0.7961 (4)	0.0336 (5)	0.76 (4)
Cl5B	0.2143 (16)	0.8801 (13)	0.824 (3)	0.044 (3)	0.24 (4)
N4	−0.13533 (18)	0.71888 (15)	0.89436 (11)	0.0244 (3)
C40	−0.2445 (2)	0.74139 (16)	0.93900 (12)	0.0208 (3)
C41	−0.3854 (2)	0.77318 (19)	0.99456 (15)	0.0279 (3)
H41A	−0.3387	0.8522	1.0616	0.042*
H41B	−0.4277	0.6828	1.0175	0.042*
H41C	−0.4848	0.8060	0.9421	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.01273 (12)	0.01373 (12)	0.01410 (13)	0.00460 (9)	0.00394 (10)	0.00417 (9)
O1	0.0253 (5)	0.0156 (5)	0.0146 (5)	0.0073 (4)	0.0004 (4)	0.0027 (4)
C10A	0.0752 (15)	0.0253 (9)	0.0274 (9)	0.0128 (9)	−0.0216 (9)	0.0059 (7)
C11A	0.038 (4)	0.028 (3)	0.027 (3)	−0.004 (3)	−0.001 (3)	0.012 (2)
C12A	0.0370 (10)	0.0315 (9)	0.0244 (8)	0.0016 (7)	0.0012 (7)	−0.0032 (7)
C10B	0.0752 (15)	0.0253 (9)	0.0274 (9)	0.0128 (9)	−0.0216 (9)	0.0059 (7)
C11B	0.053 (3)	0.029 (2)	0.0242 (19)	0.003 (2)	−0.016 (2)	0.0030 (14)
C12B	0.0370 (10)	0.0315 (9)	0.0244 (8)	0.0016 (7)	0.0012 (7)	−0.0032 (7)
C13	0.0417 (10)	0.0211 (8)	0.0234 (8)	0.0122 (7)	0.0034 (7)	−0.0015 (6)
N2	0.0174 (6)	0.0189 (6)	0.0253 (6)	0.0042 (5)	0.0070 (5)	0.0034 (5)
C20	0.0167 (7)	0.0168 (7)	0.0343 (8)	−0.0019 (5)	0.0058 (6)	−0.0033 (6)
C21	0.0209 (8)	0.0282 (9)	0.0719 (14)	0.0004 (7)	0.0202 (9)	−0.0129 (9)
N3	0.0201 (6)	0.0186 (6)	0.0202 (6)	0.0040 (5)	0.0063 (5)	0.0050 (5)
C30	0.0212 (7)	0.0201 (7)	0.0177 (7)	0.0029 (5)	0.0058 (6)	0.0025 (5)
C31	0.0483 (11)	0.0221 (8)	0.0248 (8)	0.0008 (7)	0.0125 (7)	0.0102 (6)
Co2	0.02154 (11)	0.01861 (10)	0.01895 (10)	0.00355 (7)	0.00517 (8)	0.00178 (7)
Cl3	0.0296 (2)	0.03022 (19)	0.02602 (19)	0.01043 (15)	0.00729 (15)	0.01106 (15)
Cl4	0.0440 (2)	0.0332 (2)	0.02057 (19)	0.01670 (18)	−0.00327 (17)	−0.00293 (15)
Cl5A	0.0363 (9)	0.0190 (5)	0.0509 (11)	0.0024 (5)	0.0215 (9)	0.0067 (6)
Cl5B	0.0252 (19)	0.0276 (16)	0.076 (8)	−0.0012 (11)	0.003 (3)	0.014 (3)
N4	0.0251 (7)	0.0270 (7)	0.0206 (6)	0.0057 (5)	0.0050 (5)	0.0041 (5)
C40	0.0219 (7)	0.0190 (7)	0.0187 (7)	0.0025 (6)	0.0003 (6)	0.0033 (5)
C41	0.0231 (8)	0.0302 (8)	0.0320 (9)	0.0059 (6)	0.0097 (7)	0.0059 (7)

Geometric parameters (Å, º)

Co1—O1^i	2.0888 (10)	C12B—H12D	0.9900
Co1—O1	2.0888 (10)	C13—H13A	0.9900
Co1—N3	2.0979 (12)	C13—H13B	0.9900
Co1—N3^i	2.0979 (12)	N2—C20	1.1334 (19)
Co1—N2^i	2.1017 (12)	C20—C21	1.449 (2)
Co1—N2	2.1017 (12)	C21—H21A	0.9800
O1—C10B	1.4465 (19)	C21—H21B	0.9800
O1—C10A	1.4465 (19)	C21—H21C	0.9800
O1—C13	1.4591 (17)	N3—C30	1.1354 (19)
C10A—C11A	1.425 (8)	C30—C31	1.451 (2)
C10A—H10A	0.9900	C31—H31A	0.9800
C10A—H10B	0.9900	C31—H31B	0.9800
C11A—C12A	1.523 (7)	C31—H31C	0.9800
C11A—H11A	0.9900	C31—H31D	0.9800
C11A—H11B	0.9900	C31—H31E	0.9800
C12A—C13	1.494 (2)	C31—H31F	0.9800
C12A—H12A	0.9900	Co2—N4	2.0248 (13)
C12A—H12B	0.9900	Co2—Cl5B	2.190 (13)
C10B—C11B	1.507 (5)	Co2—Cl4	2.2439 (5)
C10B—H10C	0.9900	Co2—Cl3	2.2479 (4)
C10B—H10D	0.9900	Co2—Cl5A	2.264 (4)
C11B—C12B	1.466 (5)	N4—C40	1.134 (2)
C11B—H11C	0.9900	C40—C41	1.451 (2)
C11B—H11D	0.9900	C41—H41A	0.9800
C12B—C13	1.494 (2)	C41—H41B	0.9800
C12B—H12C	0.9900	C41—H41C	0.9800
O1^i—Co1—O1	180.0	O1—C13—C12B	106.13 (13)
O1^i—Co1—N3	89.76 (4)	O1—C13—C12A	106.13 (13)
O1—Co1—N3	90.24 (4)	O1—C13—H13A	110.5
O1^i—Co1—N3^i	90.24 (4)	C12A—C13—H13A	110.5
O1—Co1—N3^i	89.76 (4)	O1—C13—H13B	110.5
N3—Co1—N3^i	180.0	C12A—C13—H13B	110.5
O1^i—Co1—N2^i	89.93 (4)	H13A—C13—H13B	108.7
O1—Co1—N2^i	90.07 (4)	C20—N2—Co1	172.92 (12)
N3—Co1—N2^i	87.31 (5)	N2—C20—C21	178.93 (17)
N3^i—Co1—N2^i	92.69 (5)	C20—C21—H21A	109.5
O1^i—Co1—N2	90.07 (4)	C20—C21—H21B	109.5
O1—Co1—N2	89.93 (4)	H21A—C21—H21B	109.5
N3—Co1—N2	92.69 (5)	C20—C21—H21C	109.5
N3^i—Co1—N2	87.31 (5)	H21A—C21—H21C	109.5
N2^i—Co1—N2	180.0	H21B—C21—H21C	109.5
C10B—O1—C13	108.52 (12)	C30—N3—Co1	170.53 (12)
C10A—O1—C13	108.52 (12)	N3—C30—C31	179.12 (17)
C10B—O1—Co1	124.46 (9)	C30—C31—H31A	109.5
C10A—O1—Co1	124.46 (9)	C30—C31—H31B	109.5
C13—O1—Co1	124.67 (9)	H31A—C31—H31B	109.5
C11A—C10A—O1	109.1 (3)	C30—C31—H31C	109.5
C11A—C10A—H10A	109.9	H31A—C31—H31C	109.5
O1—C10A—H10A	109.9	H31B—C31—H31C	109.5
C11A—C10A—H10B	109.9	C30—C31—H31D	109.5
O1—C10A—H10B	109.9	H31A—C31—H31D	141.1
H10A—C10A—H10B	108.3	H31B—C31—H31D	56.3
C10A—C11A—C12A	106.4 (4)	H31C—C31—H31D	56.3
C10A—C11A—H11A	110.5	C30—C31—H31E	109.5
C12A—C11A—H11A	110.5	H31A—C31—H31E	56.3
C10A—C11A—H11B	110.5	H31B—C31—H31E	141.1
C12A—C11A—H11B	110.5	H31C—C31—H31E	56.3
H11A—C11A—H11B	108.6	H31D—C31—H31E	109.5
C13—C12A—C11A	104.0 (3)	C30—C31—H31F	109.5
C13—C12A—H12A	111.0	H31A—C31—H31F	56.3
C11A—C12A—H12A	111.0	H31B—C31—H31F	56.3
C13—C12A—H12B	111.0	H31C—C31—H31F	141.1
C11A—C12A—H12B	111.0	H31D—C31—H31F	109.5
H12A—C12A—H12B	109.0	H31E—C31—H31F	109.5
O1—C10B—C11B	105.1 (2)	N4—Co2—Cl5B	106.1 (7)
O1—C10B—H10C	110.7	N4—Co2—Cl4	102.04 (4)
C11B—C10B—H10C	110.7	Cl5B—Co2—Cl4	118.0 (9)
O1—C10B—H10D	110.7	N4—Co2—Cl3	109.16 (4)
C11B—C10B—H10D	110.7	Cl5B—Co2—Cl3	108.4 (4)
H10C—C10B—H10D	108.8	Cl4—Co2—Cl3	112.505 (17)
C12B—C11B—C10B	105.1 (3)	N4—Co2—Cl5A	111.05 (9)
C12B—C11B—H11C	110.7	Cl4—Co2—Cl5A	109.56 (14)
C10B—C11B—H11C	110.7	Cl3—Co2—Cl5A	112.10 (13)
C12B—C11B—H11D	110.7	C40—N4—Co2	174.12 (13)
C10B—C11B—H11D	110.7	N4—C40—C41	178.57 (16)
H11C—C11B—H11D	108.8	C40—C41—H41A	109.5
C11B—C12B—C13	107.7 (2)	C40—C41—H41B	109.5
C11B—C12B—H12C	110.2	H41A—C41—H41B	109.5
C13—C12B—H12C	110.2	C40—C41—H41C	109.5
C11B—C12B—H12D	110.2	H41A—C41—H41C	109.5
C13—C12B—H12D	110.2	H41B—C41—H41C	109.5
H12C—C12B—H12D	108.5
C13—O1—C10A—C11A	0.8 (5)	C10B—C11B—C12B—C13	−18.5 (6)
Co1—O1—C10A—C11A	−162.5 (5)	C10B—O1—C13—C12B	14.4 (2)
O1—C10A—C11A—C12A	−15.4 (8)	Co1—O1—C13—C12B	177.62 (10)
C10A—C11A—C12A—C13	23.6 (7)	C10A—O1—C13—C12A	14.4 (2)
C13—O1—C10B—C11B	−25.8 (4)	Co1—O1—C13—C12A	177.62 (10)
Co1—O1—C10B—C11B	171.0 (4)	C11B—C12B—C13—O1	3.1 (4)
O1—C10B—C11B—C12B	27.1 (6)	C11A—C12A—C13—O1	−22.9 (5)

Symmetry code: (i) −x+1, −y, −z+1.

(compound-2') catena-Poly[[tetrakis(propan-2-ol-κO)cobalt(II)]-µ-chlorido-[dichloridocobalt(II)]-µ-chlorido]

Crystal data

[Co2Cl4(C3H8O)4]	F(000) = 1032
Mr = 500.03	Dx = 1.506 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.5619 (9) Å	Cell parameters from 9907 reflections
b = 9.4778 (5) Å	θ = 2.9–28.3°
c = 15.6842 (9) Å	µ = 2.00 mm^−1
β = 116.411 (2)°	T = 100 K
V = 2205.0 (2) Å^3	Plate, light blue
Z = 4	0.29 × 0.23 × 0.08 mm

Data collection

Bruker D8 Venture/Photon 100 CMOS diffractometer	2538 independent reflections
Radiation source: fine-focus sealed tube	2199 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.070
Detector resolution: 10.4167 pixels mm^-1	θmax = 27.5°, θmin = 4.3°
φ and ω scans	h = −21→21
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −12→12
Tmin = 0.668, Tmax = 0.746	l = −20→20
43674 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.073	w = 1/[σ^2(Fo^2) + (0.0485P)^2 + 0.0879P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
2538 reflections	Δρmax = 0.83 e Å^−3
114 parameters	Δρmin = −0.52 e Å^−3
2 restraints

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Co1	0.5000	0.5000	0.5000	0.00902 (10)
Co2	0.5000	0.52686 (3)	0.2500	0.01039 (10)
Cl1	0.51520 (3)	0.65613 (4)	0.37870 (3)	0.01394 (11)
Cl2	0.37147 (3)	0.39771 (5)	0.19750 (3)	0.01507 (12)
O1	0.45122 (9)	0.66345 (12)	0.54980 (10)	0.0145 (3)
C10	0.45036 (12)	0.81465 (18)	0.53165 (13)	0.0144 (4)
H10	0.4899	0.8324	0.4997	0.017*
C11	0.35586 (16)	0.8579 (2)	0.46434 (17)	0.0366 (6)
H11A	0.3551	0.9582	0.4487	0.055*
H11B	0.3160	0.8419	0.4945	0.055*
H11C	0.3349	0.8017	0.4059	0.055*
C12	0.48898 (14)	0.8938 (2)	0.62454 (13)	0.0206 (4)
H12A	0.4921	0.9946	0.6123	0.031*
H12B	0.5497	0.8584	0.6654	0.031*
H12C	0.4503	0.8800	0.6563	0.031*
O2	0.62701 (9)	0.55147 (15)	0.60069 (10)	0.0176 (3)
C20	0.70995 (12)	0.59233 (19)	0.59773 (14)	0.0148 (4)
H20	0.7068	0.5614	0.5354	0.018*
C21	0.71953 (16)	0.7510 (2)	0.60417 (16)	0.0295 (5)
H21A	0.7747	0.7785	0.6000	0.044*
H21B	0.7228	0.7832	0.6650	0.044*
H21C	0.6673	0.7943	0.5517	0.044*
C22	0.78836 (15)	0.5186 (2)	0.67626 (17)	0.0280 (5)
H22A	0.8444	0.5461	0.6740	0.042*
H22B	0.7803	0.4163	0.6679	0.042*
H22C	0.7913	0.5454	0.7379	0.042*
H1	0.4247 (16)	0.644 (3)	0.5815 (17)	0.040 (8)*
H2	0.6300 (16)	0.562 (3)	0.6529 (13)	0.025 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.01228 (18)	0.00627 (16)	0.00915 (18)	0.00068 (12)	0.00534 (14)	−0.00011 (12)
Co2	0.01247 (18)	0.01045 (17)	0.00877 (18)	0.000	0.00519 (14)	0.000
Cl1	0.0238 (2)	0.0093 (2)	0.0113 (2)	−0.00129 (15)	0.01021 (18)	−0.00060 (14)
Cl2	0.0143 (2)	0.0180 (2)	0.0139 (2)	−0.00370 (16)	0.00719 (18)	−0.00318 (16)
O1	0.0250 (7)	0.0068 (6)	0.0178 (7)	0.0030 (5)	0.0150 (6)	0.0022 (5)
C10	0.0227 (10)	0.0067 (8)	0.0152 (9)	0.0015 (7)	0.0095 (8)	0.0018 (7)
C11	0.0373 (13)	0.0208 (11)	0.0310 (13)	0.0106 (10)	−0.0035 (11)	0.0052 (10)
C12	0.0278 (11)	0.0139 (10)	0.0206 (11)	−0.0022 (7)	0.0114 (9)	−0.0038 (7)
O2	0.0151 (7)	0.0273 (8)	0.0120 (7)	−0.0060 (5)	0.0075 (6)	−0.0042 (6)
C20	0.0130 (8)	0.0174 (9)	0.0167 (9)	−0.0011 (7)	0.0090 (7)	−0.0008 (7)
C21	0.0345 (12)	0.0185 (10)	0.0336 (13)	−0.0069 (9)	0.0136 (10)	−0.0022 (9)
C22	0.0209 (11)	0.0342 (12)	0.0270 (12)	0.0080 (9)	0.0090 (10)	0.0026 (9)

Geometric parameters (Å, º)

Co1—O2	2.0498 (13)	C11—H11B	0.9800
Co1—O2^i	2.0498 (13)	C11—H11C	0.9800
Co1—O1^i	2.0552 (12)	C12—H12A	0.9800
Co1—O1	2.0552 (12)	C12—H12B	0.9800
Co1—Cl1	2.5097 (4)	C12—H12C	0.9800
Co1—Cl1^i	2.5098 (4)	O2—C20	1.448 (2)
Co2—Cl2	2.2690 (5)	O2—H2	0.804 (16)
Co2—Cl2^ii	2.2689 (5)	C20—C22	1.506 (3)
Co2—Cl1^ii	2.2775 (4)	C20—C21	1.511 (3)
Co2—Cl1	2.2775 (4)	C20—H20	1.0000
O1—C10	1.460 (2)	C21—H21A	0.9800
O1—H1	0.817 (16)	C21—H21B	0.9800
C10—C11	1.504 (3)	C21—H21C	0.9800
C10—C12	1.505 (2)	C22—H22A	0.9800
C10—H10	1.0000	C22—H22B	0.9800
C11—H11A	0.9800	C22—H22C	0.9800
O2—Co1—O2^i	180.00 (6)	C10—C11—H11B	109.5
O2—Co1—O1^i	91.72 (5)	H11A—C11—H11B	109.5
O2^i—Co1—O1^i	88.28 (5)	C10—C11—H11C	109.5
O2—Co1—O1	88.28 (5)	H11A—C11—H11C	109.5
O2^i—Co1—O1	91.72 (5)	H11B—C11—H11C	109.5
O1^i—Co1—O1	180.00 (7)	C10—C12—H12A	109.5
O2—Co1—Cl1	91.67 (4)	C10—C12—H12B	109.5
O2^i—Co1—Cl1	88.33 (4)	H12A—C12—H12B	109.5
O1^i—Co1—Cl1	88.13 (4)	C10—C12—H12C	109.5
O1—Co1—Cl1	91.87 (4)	H12A—C12—H12C	109.5
O2—Co1—Cl1^i	88.33 (4)	H12B—C12—H12C	109.5
O2^i—Co1—Cl1^i	91.67 (4)	C20—O2—Co1	134.60 (11)
O1^i—Co1—Cl1^i	91.87 (4)	C20—O2—H2	111.8 (18)
O1—Co1—Cl1^i	88.13 (4)	Co1—O2—H2	113.0 (18)
Cl1—Co1—Cl1^i	180.00 (2)	O2—C20—C22	109.57 (16)
Cl2—Co2—Cl2^ii	114.70 (3)	O2—C20—C21	109.70 (16)
Cl2—Co2—Cl1^ii	104.628 (16)	C22—C20—C21	112.36 (18)
Cl2^ii—Co2—Cl1^ii	109.141 (15)	O2—C20—H20	108.4
Cl2—Co2—Cl1	109.141 (15)	C22—C20—H20	108.4
Cl2^ii—Co2—Cl1	104.629 (16)	C21—C20—H20	108.4
Cl1^ii—Co2—Cl1	114.91 (3)	C20—C21—H21A	109.5
Co2—Cl1—Co1	110.234 (18)	C20—C21—H21B	109.5
C10—O1—Co1	129.58 (11)	H21A—C21—H21B	109.5
C10—O1—H1	112.0 (19)	C20—C21—H21C	109.5
Co1—O1—H1	118.3 (19)	H21A—C21—H21C	109.5
O1—C10—C11	108.73 (16)	H21B—C21—H21C	109.5
O1—C10—C12	109.73 (15)	C20—C22—H22A	109.5
C11—C10—C12	113.89 (17)	C20—C22—H22B	109.5
O1—C10—H10	108.1	H22A—C22—H22B	109.5
C11—C10—H10	108.1	C20—C22—H22C	109.5
C12—C10—H10	108.1	H22A—C22—H22C	109.5
C10—C11—H11A	109.5	H22B—C22—H22C	109.5
Co1—O1—C10—C11	105.60 (17)	Co1—O2—C20—C22	−138.24 (15)
Co1—O1—C10—C12	−129.23 (14)	Co1—O2—C20—C21	97.97 (19)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···Cl2^i	0.80 (2)	2.39 (2)	3.1907 (15)	176 (2)
O1—H1···Cl2^iii	0.82 (2)	2.38 (2)	3.1888 (13)	170 (3)

Symmetry codes: (i) −x+1, −y+1, −z+1; (iii) x, −y+1, z+1/2.

(compound-3) Di-µ-chlorido-1:2κ⁴Cl:Cl-dichlorido-2κ²Cl-tetrakis(tetrahydrofuran-1κO)dicobalt(II)

Crystal data

[Co2Cl4(C4H8O)4]	F(000) = 1128
Mr = 548.07	Dx = 1.607 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.733 (3) Å	Cell parameters from 4769 reflections
b = 9.6318 (17) Å	θ = 3.3–27.9°
c = 15.993 (4) Å	µ = 1.95 mm^−1
β = 93.737 (8)°	T = 100 K
V = 2264.7 (8) Å^3	Plate, blue
Z = 4	0.15 × 0.10 × 0.07 mm

Data collection

Bruker D8 Venture/Photon 100 CMOS diffractometer	3970 independent reflections
Radiation source: fine-focus sealed tube	2302 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.104
Detector resolution: 10.4167 pixels mm^-1	θmax = 25.0°, θmin = 2.9°
φ and ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −10→11
Tmin = 0.675, Tmax = 1.000	l = −19→19
13815 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H-atom parameters constrained
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0387P)^2] where P = (Fo^2 + 2Fc^2)/3
3970 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.76 e Å^−3
0 restraints	Δρmin = −0.65 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.0924 (5)	0.3030 (8)	0.5282 (4)	0.0285 (18)
H1A	0.0470	0.3747	0.5105	0.034*
H1B	0.1089	0.3136	0.5889	0.034*
C2	0.0566 (5)	0.1592 (8)	0.5085 (5)	0.0312 (19)
H2A	0.0210	0.1237	0.5543	0.037*
H2B	0.0177	0.1588	0.4556	0.037*
C3	0.1407 (5)	0.0739 (9)	0.5001 (5)	0.039 (2)
H3A	0.1313	0.0060	0.4539	0.047*
H3B	0.1570	0.0230	0.5527	0.047*
C4	0.2146 (5)	0.1770 (8)	0.4815 (4)	0.0271 (18)
H4A	0.2650	0.1731	0.5255	0.033*
H4B	0.2392	0.1562	0.4267	0.033*
C5	0.0802 (5)	0.4427 (8)	0.3227 (4)	0.0270 (18)
H5A	0.0249	0.4401	0.3548	0.032*
H5B	0.1054	0.3477	0.3196	0.032*
C6	0.0594 (5)	0.5022 (10)	0.2362 (4)	0.037 (2)
H6A	−0.0001	0.4695	0.2114	0.044*
H6B	0.1075	0.4790	0.1981	0.044*
C7	0.0577 (5)	0.6585 (9)	0.2556 (4)	0.035 (2)
H7A	0.0735	0.7138	0.2065	0.041*
H7B	−0.0029	0.6876	0.2724	0.041*
C8	0.1282 (5)	0.6747 (8)	0.3265 (4)	0.0296 (19)
H8A	0.1843	0.7158	0.3062	0.036*
H8B	0.1055	0.7363	0.3701	0.036*
C9	0.3031 (5)	0.3784 (8)	0.2875 (3)	0.0239 (17)
H9A	0.2905	0.4729	0.2652	0.029*
H9B	0.2496	0.3187	0.2732	0.029*
C10	0.3870 (6)	0.3191 (10)	0.2525 (4)	0.042 (2)
H10A	0.4316	0.3930	0.2420	0.050*
H10B	0.3718	0.2682	0.1997	0.050*
C11	0.4236 (6)	0.2216 (9)	0.3211 (4)	0.037 (2)
H11A	0.3887	0.1338	0.3211	0.045*
H11B	0.4888	0.2008	0.3162	0.045*
C12	0.4087 (5)	0.3079 (8)	0.3975 (4)	0.0279 (18)
H12A	0.4038	0.2479	0.4473	0.033*
H12B	0.4596	0.3738	0.4088	0.033*
C13	0.4137 (5)	0.6644 (8)	0.4086 (4)	0.0273 (18)
H13A	0.4180	0.6198	0.3532	0.033*
H13B	0.4491	0.6088	0.4513	0.033*
C14	0.4492 (5)	0.8129 (8)	0.4072 (4)	0.0275 (18)
H14A	0.5151	0.8169	0.4238	0.033*
H14B	0.4381	0.8553	0.3511	0.033*
C15	0.3940 (5)	0.8834 (9)	0.4711 (4)	0.034 (2)
H15A	0.4191	0.8644	0.5289	0.041*
H15B	0.3913	0.9851	0.4620	0.041*
C16	0.3025 (5)	0.8181 (8)	0.4547 (4)	0.0290 (18)
H16A	0.2683	0.8198	0.5060	0.035*
H16B	0.2670	0.8686	0.4097	0.035*
O1	0.1722 (3)	0.3125 (5)	0.4799 (3)	0.0230 (11)
O2	0.1468 (3)	0.5374 (5)	0.3605 (2)	0.0235 (12)
O3	0.3238 (3)	0.3823 (5)	0.3781 (2)	0.0209 (11)
O4	0.3187 (3)	0.6758 (5)	0.4293 (2)	0.0189 (11)
Cl1	0.19248 (13)	0.4680 (2)	0.76069 (10)	0.0300 (5)
Cl2	0.32533 (14)	0.7820 (2)	0.69316 (11)	0.0378 (5)
Cl3	0.14672 (11)	0.62825 (19)	0.55023 (9)	0.0212 (4)
Cl4	0.34831 (11)	0.44962 (19)	0.57916 (9)	0.0209 (4)
Co1	0.24425 (6)	0.49735 (10)	0.45818 (5)	0.0157 (2)
Co2	0.25485 (6)	0.58390 (11)	0.65805 (5)	0.0214 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.024 (4)	0.026 (5)	0.036 (4)	−0.005 (4)	0.010 (3)	0.001 (4)
C2	0.028 (5)	0.019 (5)	0.047 (4)	−0.003 (4)	0.012 (3)	0.002 (4)
C3	0.036 (5)	0.031 (5)	0.051 (5)	−0.005 (4)	0.020 (4)	0.005 (4)
C4	0.033 (5)	0.017 (5)	0.031 (4)	0.013 (4)	0.000 (3)	−0.003 (3)
C5	0.029 (4)	0.028 (5)	0.024 (3)	0.005 (4)	0.000 (3)	−0.001 (3)
C6	0.028 (5)	0.062 (7)	0.019 (3)	0.004 (5)	−0.006 (3)	0.000 (4)
C7	0.034 (5)	0.031 (5)	0.038 (4)	−0.005 (4)	−0.007 (3)	0.015 (4)
C8	0.036 (5)	0.026 (5)	0.027 (4)	0.005 (4)	0.003 (3)	0.008 (4)
C9	0.032 (4)	0.024 (5)	0.015 (3)	0.001 (4)	−0.001 (3)	−0.004 (3)
C10	0.042 (5)	0.056 (7)	0.030 (4)	−0.009 (5)	0.018 (4)	−0.015 (4)
C11	0.029 (5)	0.042 (6)	0.041 (4)	0.004 (4)	0.007 (3)	−0.014 (4)
C12	0.023 (4)	0.033 (5)	0.028 (4)	0.009 (4)	0.002 (3)	−0.003 (3)
C13	0.033 (5)	0.027 (5)	0.023 (3)	0.003 (4)	0.010 (3)	−0.004 (3)
C14	0.033 (5)	0.024 (5)	0.027 (4)	−0.009 (4)	0.010 (3)	−0.002 (3)
C15	0.041 (5)	0.028 (5)	0.033 (4)	0.001 (4)	0.006 (3)	0.000 (4)
C16	0.029 (5)	0.022 (5)	0.036 (4)	0.002 (4)	0.001 (3)	0.002 (4)
O1	0.022 (3)	0.018 (3)	0.030 (2)	0.003 (2)	0.008 (2)	0.004 (2)
O2	0.022 (3)	0.023 (3)	0.024 (2)	0.000 (2)	−0.0101 (19)	−0.001 (2)
O3	0.025 (3)	0.024 (3)	0.014 (2)	0.005 (2)	0.0044 (18)	−0.002 (2)
O4	0.019 (3)	0.017 (3)	0.021 (2)	−0.003 (2)	0.0024 (18)	−0.002 (2)
Cl1	0.0316 (11)	0.0380 (13)	0.0209 (8)	0.0032 (9)	0.0064 (7)	0.0015 (8)
Cl2	0.0374 (12)	0.0383 (13)	0.0376 (10)	−0.0125 (11)	0.0025 (8)	−0.0161 (9)
Cl3	0.0157 (9)	0.0274 (11)	0.0203 (8)	0.0017 (8)	0.0006 (6)	−0.0014 (7)
Cl4	0.0193 (9)	0.0281 (11)	0.0153 (7)	0.0059 (8)	0.0015 (6)	−0.0003 (7)
Co1	0.0165 (5)	0.0167 (5)	0.0138 (4)	0.0013 (4)	0.0004 (3)	0.0000 (4)
Co2	0.0216 (5)	0.0274 (6)	0.0153 (4)	0.0004 (5)	0.0020 (4)	−0.0041 (4)

Geometric parameters (Å, º)

C1—O1	1.450 (8)	C10—H10A	0.9900
C1—C2	1.509 (11)	C10—H10B	0.9900
C1—H1A	0.9900	C11—C12	1.506 (9)
C1—H1B	0.9900	C11—H11A	0.9900
C2—C3	1.499 (11)	C11—H11B	0.9900
C2—H2A	0.9900	C12—O3	1.458 (8)
C2—H2B	0.9900	C12—H12A	0.9900
C3—C4	1.517 (11)	C12—H12B	0.9900
C3—H3A	0.9900	C13—O4	1.463 (8)
C3—H3B	0.9900	C13—C14	1.524 (10)
C4—O1	1.447 (8)	C13—H13A	0.9900
C4—H4A	0.9900	C13—H13B	0.9900
C4—H4B	0.9900	C14—C15	1.510 (9)
C5—O2	1.443 (8)	C14—H14A	0.9900
C5—C6	1.511 (9)	C14—H14B	0.9900
C5—H5A	0.9900	C15—C16	1.494 (10)
C5—H5B	0.9900	C15—H15A	0.9900
C6—C7	1.537 (12)	C15—H15B	0.9900
C6—H6A	0.9900	C16—O4	1.453 (9)
C6—H6B	0.9900	C16—H16A	0.9900
C7—C8	1.494 (9)	C16—H16B	0.9900
C7—H7A	0.9900	O1—Co1	2.113 (5)
C7—H7B	0.9900	O2—Co1	2.088 (4)
C8—O2	1.449 (9)	O3—Co1	2.107 (4)
C8—H8A	0.9900	O4—Co1	2.107 (5)
C8—H8B	0.9900	Cl1—Co2	2.232 (2)
C9—O3	1.462 (7)	Cl2—Co2	2.227 (2)
C9—C10	1.503 (10)	Cl3—Co2	2.3099 (19)
C9—H9A	0.9900	Cl3—Co1	2.4693 (19)
C9—H9B	0.9900	Cl4—Co2	2.3210 (19)
C10—C11	1.516 (11)	Cl4—Co1	2.4329 (18)
O1—C1—C2	103.3 (6)	O3—C12—C11	105.4 (5)
O1—C1—H1A	111.1	O3—C12—H12A	110.7
C2—C1—H1A	111.1	C11—C12—H12A	110.7
O1—C1—H1B	111.1	O3—C12—H12B	110.7
C2—C1—H1B	111.1	C11—C12—H12B	110.7
H1A—C1—H1B	109.1	H12A—C12—H12B	108.8
C3—C2—C1	104.0 (6)	O4—C13—C14	105.5 (6)
C3—C2—H2A	111.0	O4—C13—H13A	110.6
C1—C2—H2A	111.0	C14—C13—H13A	110.6
C3—C2—H2B	111.0	O4—C13—H13B	110.6
C1—C2—H2B	111.0	C14—C13—H13B	110.6
H2A—C2—H2B	109.0	H13A—C13—H13B	108.8
C2—C3—C4	105.5 (7)	C15—C14—C13	102.2 (5)
C2—C3—H3A	110.6	C15—C14—H14A	111.3
C4—C3—H3A	110.6	C13—C14—H14A	111.3
C2—C3—H3B	110.6	C15—C14—H14B	111.3
C4—C3—H3B	110.6	C13—C14—H14B	111.3
H3A—C3—H3B	108.8	H14A—C14—H14B	109.2
O1—C4—C3	106.2 (6)	C16—C15—C14	102.2 (6)
O1—C4—H4A	110.5	C16—C15—H15A	111.3
C3—C4—H4A	110.5	C14—C15—H15A	111.3
O1—C4—H4B	110.5	C16—C15—H15B	111.3
C3—C4—H4B	110.5	C14—C15—H15B	111.3
H4A—C4—H4B	108.7	H15A—C15—H15B	109.2
O2—C5—C6	103.6 (6)	O4—C16—C15	106.5 (6)
O2—C5—H5A	111.0	O4—C16—H16A	110.4
C6—C5—H5A	111.0	C15—C16—H16A	110.4
O2—C5—H5B	111.0	O4—C16—H16B	110.4
C6—C5—H5B	111.0	C15—C16—H16B	110.4
H5A—C5—H5B	109.0	H16A—C16—H16B	108.6
C5—C6—C7	101.0 (6)	C4—O1—C1	107.3 (5)
C5—C6—H6A	111.6	C4—O1—Co1	122.8 (4)
C7—C6—H6A	111.6	C1—O1—Co1	125.0 (4)
C5—C6—H6B	111.6	C5—O2—C8	108.2 (5)
C7—C6—H6B	111.6	C5—O2—Co1	127.7 (4)
H6A—C6—H6B	109.4	C8—O2—Co1	123.6 (4)
C8—C7—C6	103.7 (6)	C12—O3—C9	108.7 (5)
C8—C7—H7A	111.0	C12—O3—Co1	129.2 (3)
C6—C7—H7A	111.0	C9—O3—Co1	121.9 (4)
C8—C7—H7B	111.0	C16—O4—C13	108.1 (5)
C6—C7—H7B	111.0	C16—O4—Co1	127.6 (4)
H7A—C7—H7B	109.0	C13—O4—Co1	120.5 (4)
O2—C8—C7	107.1 (6)	Co2—Cl3—Co1	87.18 (7)
O2—C8—H8A	110.3	Co2—Cl4—Co1	87.80 (7)
C7—C8—H8A	110.3	O2—Co1—O3	91.43 (17)
O2—C8—H8B	110.3	O2—Co1—O4	91.59 (18)
C7—C8—H8B	110.3	O3—Co1—O4	88.69 (18)
H8A—C8—H8B	108.5	O2—Co1—O1	87.15 (18)
O3—C9—C10	104.8 (6)	O3—Co1—O1	87.85 (18)
O3—C9—H9A	110.8	O4—Co1—O1	176.29 (17)
C10—C9—H9A	110.8	O2—Co1—Cl4	175.59 (14)
O3—C9—H9B	110.8	O3—Co1—Cl4	92.16 (13)
C10—C9—H9B	110.8	O4—Co1—Cl4	91.05 (13)
H9A—C9—H9B	108.9	O1—Co1—Cl4	90.43 (13)
C9—C10—C11	103.2 (6)	O2—Co1—Cl3	87.31 (14)
C9—C10—H10A	111.1	O3—Co1—Cl3	178.20 (14)
C11—C10—H10A	111.1	O4—Co1—Cl3	92.63 (13)
C9—C10—H10B	111.1	O1—Co1—Cl3	90.80 (13)
C11—C10—H10B	111.1	Cl4—Co1—Cl3	89.04 (6)
H10A—C10—H10B	109.1	Cl2—Co2—Cl1	116.79 (8)
C12—C11—C10	100.5 (6)	Cl2—Co2—Cl3	108.50 (8)
C12—C11—H11A	111.7	Cl1—Co2—Cl3	110.15 (8)
C10—C11—H11A	111.7	Cl2—Co2—Cl4	109.34 (8)
C12—C11—H11B	111.7	Cl1—Co2—Cl4	114.10 (8)
C10—C11—H11B	111.7	Cl3—Co2—Cl4	95.85 (6)
H11A—C11—H11B	109.4
O1—C1—C2—C3	35.2 (7)	C2—C1—O1—C4	−36.3 (7)
C1—C2—C3—C4	−21.5 (8)	C2—C1—O1—Co1	168.0 (4)
C2—C3—C4—O1	0.0 (8)	C6—C5—O2—C8	31.6 (7)
O2—C5—C6—C7	−40.1 (7)	C6—C5—O2—Co1	−155.6 (4)
C5—C6—C7—C8	34.1 (8)	C7—C8—O2—C5	−9.4 (8)
C6—C7—C8—O2	−16.1 (8)	C7—C8—O2—Co1	177.4 (4)
O3—C9—C10—C11	31.7 (8)	C11—C12—O3—C9	−17.3 (8)
C9—C10—C11—C12	−41.2 (8)	C11—C12—O3—Co1	168.5 (5)
C10—C11—C12—O3	35.9 (7)	C10—C9—O3—C12	−9.1 (8)
O4—C13—C14—C15	30.7 (7)	C10—C9—O3—Co1	165.6 (5)
C13—C14—C15—C16	−38.8 (7)	C15—C16—O4—C13	−14.7 (7)
C14—C15—C16—O4	33.7 (7)	C15—C16—O4—Co1	143.2 (4)
C3—C4—O1—C1	22.7 (7)	C14—C13—O4—C16	−10.3 (6)
C3—C4—O1—Co1	179.1 (4)	C14—C13—O4—Co1	−170.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cl3^i	0.99	2.95	3.722 (8)	135
C4—H4B···Cl1^ii	0.99	2.95	3.792 (7)	143
C6—H6A···Cl1^i	0.99	2.96	3.726 (8)	135
C8—H8A···Cl2^iii	0.99	2.84	3.737 (8)	151
C9—H9A···Cl2^iii	0.99	2.69	3.625 (8)	158
C9—H9B···Cl1^ii	0.99	2.89	3.726 (8)	143
C10—H10B···Cl4^ii	0.99	2.85	3.809 (8)	162
C11—H11B···Cl2^iv	0.99	2.76	3.721 (8)	165
C13—H13A···Cl2^iii	0.99	2.98	3.640 (7)	125
C16—H16A···Cl3	0.99	2.70	3.377 (8)	126
C1—H1A···Cl3^i	0.99	2.95	3.722 (8)	135
C4—H4B···Cl1^ii	0.99	2.95	3.792 (7)	143
C6—H6A···Cl1^i	0.99	2.96	3.726 (8)	135
C8—H8A···Cl2^iii	0.99	2.84	3.737 (8)	151
C9—H9A···Cl2^iii	0.99	2.69	3.625 (8)	158
C9—H9B···Cl1^ii	0.99	2.89	3.726 (8)	143
C10—H10B···Cl4^ii	0.99	2.85	3.809 (8)	162
C11—H11B···Cl2^iv	0.99	2.76	3.721 (8)	165
C13—H13A···Cl2^iii	0.99	2.98	3.640 (7)	125
C16—H16A···Cl3	0.99	2.70	3.377 (8)	126

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