Chloridobis(1,10-phenanthroline-κ2N,N′)(2,2,2-trichloro­acetato-κO)cobalt(II)

Pei, C.; Bai, P.; Guo, Z.

doi:10.1107/S1600536809054671

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page m102

doi:10.1107/S1600536809054671

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Chloridobis(1,10-phenanthroline-κ²N,N′)(2,2,2-trichloroacetato-κO)cobalt(II)

Changgui Pei,^a ^* Peikang Bai ^b and Zhangxia Guo ^c

^aSchool of Electronics and Computer Science and Technology, North University of China, Taiyuan 030051, People's Republic of China, ^bSchool of Materials Science and Engineering, North University of China, Taiyuan 030051, People's Republic of China, and ^cSchool of Electronic Science and Technology, North University of China, Taiyuan 030051, People's Republic of China
^*Correspondence e-mail: kxin_2010@163.com

(Received 14 December 2009; accepted 19 December 2009; online 24 December 2009)

The title compound, [Co(C₂Cl₃O₂)Cl(C₁₂H₈N₂)₂], was obtained by the reaction of trichloroacetic acid and CoCl₂ in the presence of 1,10-phenanthroline. The Co^II ion exhibits a distorted octahedral geometry, with three N atoms from two 1,10-phenanthroline ligands and the Cl⁻ ion in the equatorial plane and one O atom from the trichloroacetate ligand and one phenanthroline N atom in axial positions. This compound is isostructural with the analogous Mn^II complex. The trichloromethyl group of the trichloroacetate ligand is disordered over two positions with occupancies of 0.190 (5) and 0.810 (5).

Related literature

For the structure of isostructural Mn^IIcomplex, see: Chen et al. (2006 ).

Experimental

Crystal data

[Co(C₂Cl₃O₂)Cl(C₁₂H₈N₂)₂]
M_r = 617.16
Monoclinic, P 2₁ /c
a = 18.2170 (6) Å
b = 10.4612 (4) Å
c = 14.6638 (7) Å
β = 112.685 (1)°
V = 2578.32 (18) Å³
Z = 4
Mo Kα radiation
μ = 1.12 mm⁻¹
T = 293 K
0.26 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2005 ) T_min = 0.760, T_max = 0.824
13155 measured reflections
4536 independent reflections
3821 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.086
S = 1.01
4536 reflections
344 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.62 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—O2	2.078 (2)
Co1—N4	2.155 (2)
Co1—N3	2.161 (2)
Co1—N2	2.172 (2)
Co1—N1	2.190 (2)
Co1—Cl4	2.3985 (6)

Data collection: SMART (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809054671/gk2250sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809054671/gk2250Isup2.hkl

checkCIF report

Comment top

The molecular structure of the title compound is shown in Fig. 1. The Co atom exhibits a distorted octahedral geometry. The metal ion deviates from the plane defined by three N atoms from two phenantroline molecules and the chlorido ligand by 0.0881 (2) Å.

Related literature top

For the structure of isostructural Mn^IIcomplex, see: Chen et al. (2006).

Experimental top

The reaction was carried out by the hydrothermal method. Trichloroacetic acid (0.082 g, 0.5 mmol), CoCl₂.6H₂O_.(0.119 g, 0.5 mmol) and 1,10-phenanthroline (0.180 g, 1 mmol) were added to the airtight vessel containing 20 ml of water/methanol mixture in 2:1 ratio. The reaction was carried out at 303 K for 4 days and than cooled down. Resulting brown solution was filtered and brown block-shaped crystals appeared within a few days. Yield 76%; analysis calc. for C₂₆H₁₆Cl₄CoN₄O₂: C 50.60, H 2.61, N 9.08%; found: C 50.91, H 2.25, N 9.34%. The elemental analyses were performed with PERKIN ELMER Model 2400 Series II.

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.

Chloridobis(1,10-phenanthroline-κ²N,N')(2,2,2- trichloroacetato-κO)cobalt(II) top

Crystal data top

[Co(C₂Cl₃O₂)Cl(C₁₂H₈N₂)₂]	F(000) = 1244
M_r = 617.16	D_x = 1.595 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7284 reflections
a = 18.2170 (6) Å	θ = 2.3–28.1°
b = 10.4612 (4) Å	µ = 1.12 mm⁻¹
c = 14.6638 (7) Å	T = 293 K
β = 112.685 (1)°	Block, brown
V = 2578.32 (18) Å³	0.26 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	4536 independent reflections
Radiation source: fine-focus sealed tube	3821 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 0 pixels mm^-1	θ_max = 25.1°, θ_min = 2.3°
phi and ω scans	h = −17→21
Absorption correction: multi-scan (SADABS; Sheldrick, 2005)	k = −11→12
T_min = 0.760, T_max = 0.824	l = −17→16
13155 measured reflections

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.042P)² + 0.9036P] where P = (F_o² + 2F_c²)/3
4536 reflections	(Δ/σ)_max = 0.001
344 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.62 e Å⁻³

Crystal data top

[Co(C₂Cl₃O₂)Cl(C₁₂H₈N₂)₂]	V = 2578.32 (18) Å³
M_r = 617.16	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.2170 (6) Å	µ = 1.12 mm⁻¹
b = 10.4612 (4) Å	T = 293 K
c = 14.6638 (7) Å	0.26 × 0.20 × 0.18 mm
β = 112.685 (1)°

Data collection top

Bruker SMART APEX diffractometer	4536 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2005)	3821 reflections with I > 2σ(I)
T_min = 0.760, T_max = 0.824	R_int = 0.047
13155 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.01	Δρ_max = 0.56 e Å⁻³
4536 reflections	Δρ_min = −0.62 e Å⁻³
344 parameters

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	Occ. (<1)
Co1	0.290424 (16)	0.88315 (3)	0.12391 (2)	0.03091 (10)
N1	0.39845 (10)	0.79092 (17)	0.12432 (13)	0.0340 (4)
N2	0.36251 (10)	1.04002 (17)	0.10756 (13)	0.0360 (4)
N3	0.19137 (10)	1.00424 (18)	0.11353 (13)	0.0347 (4)
N4	0.22255 (11)	0.89736 (17)	−0.03298 (13)	0.0349 (4)
O1	0.11352 (10)	0.7113 (2)	0.04032 (17)	0.0690 (6)
O2	0.24513 (9)	0.69856 (14)	0.10847 (11)	0.0389 (4)
Cl1	0.1960 (6)	0.5139 (6)	−0.0763 (5)	0.0730 (5)	0.190 (5)
Cl2	0.229 (3)	0.430 (3)	0.132 (4)	0.0645 (8)	0.190 (5)
Cl3	0.0807 (13)	0.462 (2)	−0.0130 (11)	0.1180 (11)	0.190 (5)
Cl1'	0.23758 (16)	0.50950 (12)	−0.04800 (13)	0.0730 (5)	0.810 (5)
Cl2'	0.2220 (6)	0.4154 (7)	0.1267 (8)	0.0645 (8)	0.810 (5)
Cl3'	0.0798 (3)	0.4598 (4)	−0.0455 (2)	0.1180 (11)	0.810 (5)
Cl4	0.34432 (3)	0.89244 (5)	0.30104 (4)	0.04054 (15)
C1	0.17636 (16)	0.5183 (2)	0.02503 (19)	0.0511 (6)
C2	0.17667 (13)	0.6599 (2)	0.06043 (16)	0.0364 (5)
C4	0.41513 (14)	0.6677 (2)	0.13065 (18)	0.0424 (5)
H4	0.3759	0.6100	0.1294	0.051*
C5	0.48902 (15)	0.6199 (2)	0.13921 (19)	0.0500 (6)
H5	0.4980	0.5322	0.1423	0.060*
C6	0.54786 (14)	0.7022 (3)	0.14301 (19)	0.0491 (6)
H6	0.5975	0.6712	0.1496	0.059*
C7	0.53335 (13)	0.8331 (2)	0.13705 (16)	0.0395 (5)
C8	0.45653 (12)	0.8735 (2)	0.12710 (15)	0.0325 (5)
C9	0.43734 (12)	1.0069 (2)	0.11826 (15)	0.0327 (5)
C10	0.49480 (14)	1.0973 (2)	0.11934 (17)	0.0405 (5)
C11	0.47207 (15)	1.2252 (2)	0.10689 (19)	0.0505 (6)
H11	0.5082	1.2882	0.1071	0.061*
C12	0.39604 (16)	1.2573 (2)	0.0943 (2)	0.0547 (7)
H12	0.3797	1.3422	0.0850	0.066*
C13	0.34353 (14)	1.1621 (2)	0.09570 (19)	0.0467 (6)
H13	0.2922	1.1856	0.0878	0.056*
C14	0.57281 (14)	1.0536 (3)	0.13301 (19)	0.0498 (6)
H14	0.6118	1.1131	0.1368	0.060*
C15	0.59105 (14)	0.9289 (3)	0.14048 (19)	0.0506 (6)
H15	0.6420	0.9037	0.1480	0.061*
C16	0.23604 (15)	0.8363 (3)	−0.10371 (17)	0.0446 (6)
H16	0.2808	0.7844	−0.0865	0.054*
C17	0.18590 (17)	0.8463 (3)	−0.20312 (18)	0.0590 (7)
H17	0.1963	0.7997	−0.2508	0.071*
C18	0.12179 (17)	0.9246 (3)	−0.22945 (19)	0.0578 (7)
H18	0.0890	0.9340	−0.2958	0.069*
C19	0.10473 (14)	0.9916 (2)	−0.15691 (17)	0.0431 (5)
C20	0.15708 (12)	0.9720 (2)	−0.05844 (16)	0.0344 (5)
C21	0.14063 (12)	1.0312 (2)	0.01997 (16)	0.0328 (5)
C22	0.07409 (13)	1.1109 (2)	−0.00170 (18)	0.0389 (5)
C23	0.06112 (14)	1.1647 (2)	0.0780 (2)	0.0465 (6)
H23	0.0177	1.2182	0.0671	0.056*
C24	0.11226 (15)	1.1384 (3)	0.1715 (2)	0.0498 (6)
H24	0.1044	1.1741	0.2251	0.060*
C25	0.17703 (15)	1.0572 (2)	0.18682 (17)	0.0440 (6)
H25	0.2115	1.0397	0.2514	0.053*
C26	0.02322 (14)	1.1322 (2)	−0.1033 (2)	0.0487 (6)
H26	−0.0207	1.1857	−0.1185	0.058*
C27	0.03816 (15)	1.0759 (3)	−0.17682 (19)	0.0509 (6)
H27	0.0046	1.0919	−0.2420	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.02742 (16)	0.03019 (17)	0.03545 (17)	0.00155 (11)	0.01248 (13)	0.00274 (12)
N1	0.0299 (9)	0.0333 (10)	0.0382 (10)	0.0020 (8)	0.0124 (8)	0.0025 (8)
N2	0.0326 (10)	0.0319 (10)	0.0427 (10)	−0.0007 (8)	0.0135 (8)	0.0015 (8)
N3	0.0319 (9)	0.0373 (10)	0.0358 (9)	0.0029 (8)	0.0141 (8)	0.0018 (8)
N4	0.0331 (9)	0.0361 (10)	0.0379 (10)	0.0018 (8)	0.0165 (8)	0.0033 (8)
O1	0.0364 (10)	0.0618 (12)	0.1007 (16)	0.0080 (9)	0.0175 (10)	−0.0022 (12)
O2	0.0374 (9)	0.0346 (8)	0.0444 (9)	−0.0048 (7)	0.0153 (7)	0.0011 (7)
Cl1	0.0975 (14)	0.0771 (6)	0.0503 (7)	0.0091 (8)	0.0352 (9)	−0.0132 (5)
Cl2	0.085 (2)	0.039 (2)	0.0671 (15)	0.0147 (14)	0.0268 (15)	0.0094 (15)
Cl3	0.0788 (7)	0.0729 (7)	0.132 (2)	−0.0317 (5)	−0.0366 (18)	−0.0075 (18)
Cl1'	0.0975 (14)	0.0771 (6)	0.0503 (7)	0.0091 (8)	0.0352 (9)	−0.0132 (5)
Cl2'	0.085 (2)	0.039 (2)	0.0671 (15)	0.0147 (14)	0.0268 (15)	0.0094 (15)
Cl3'	0.0788 (7)	0.0729 (7)	0.132 (2)	−0.0317 (5)	−0.0366 (18)	−0.0075 (18)
Cl4	0.0363 (3)	0.0438 (3)	0.0378 (3)	0.0023 (2)	0.0102 (2)	0.0029 (2)
C1	0.0529 (15)	0.0415 (14)	0.0488 (14)	−0.0056 (12)	0.0083 (12)	−0.0031 (12)
C2	0.0328 (12)	0.0406 (12)	0.0364 (11)	0.0010 (10)	0.0141 (10)	0.0060 (10)
C4	0.0405 (13)	0.0347 (12)	0.0517 (14)	0.0037 (10)	0.0175 (11)	0.0037 (11)
C5	0.0478 (15)	0.0431 (14)	0.0580 (16)	0.0132 (12)	0.0191 (13)	0.0008 (12)
C6	0.0373 (13)	0.0576 (16)	0.0536 (15)	0.0134 (12)	0.0187 (11)	−0.0004 (13)
C7	0.0326 (12)	0.0509 (14)	0.0351 (12)	0.0039 (11)	0.0132 (10)	−0.0011 (11)
C8	0.0291 (11)	0.0394 (12)	0.0281 (10)	−0.0001 (9)	0.0101 (9)	0.0000 (9)
C9	0.0296 (11)	0.0386 (12)	0.0288 (10)	−0.0033 (9)	0.0100 (9)	−0.0014 (9)
C10	0.0383 (13)	0.0444 (14)	0.0375 (12)	−0.0103 (10)	0.0131 (10)	−0.0036 (10)
C11	0.0487 (15)	0.0430 (15)	0.0584 (15)	−0.0164 (12)	0.0190 (13)	−0.0025 (12)
C12	0.0532 (15)	0.0335 (13)	0.0740 (18)	−0.0048 (11)	0.0207 (14)	0.0020 (13)
C13	0.0406 (13)	0.0348 (13)	0.0637 (16)	0.0012 (11)	0.0189 (12)	0.0033 (12)
C14	0.0342 (13)	0.0600 (17)	0.0561 (15)	−0.0138 (12)	0.0185 (11)	−0.0052 (13)
C15	0.0294 (12)	0.0687 (18)	0.0535 (15)	−0.0018 (12)	0.0159 (11)	−0.0054 (14)
C16	0.0477 (13)	0.0512 (14)	0.0424 (13)	0.0060 (12)	0.0257 (11)	0.0028 (12)
C17	0.0686 (18)	0.077 (2)	0.0373 (13)	0.0120 (16)	0.0266 (13)	−0.0001 (13)
C18	0.0593 (17)	0.0757 (19)	0.0336 (13)	0.0056 (15)	0.0126 (12)	0.0058 (13)
C19	0.0401 (13)	0.0494 (14)	0.0367 (12)	−0.0021 (11)	0.0114 (10)	0.0057 (11)
C20	0.0304 (11)	0.0355 (12)	0.0370 (11)	−0.0028 (9)	0.0128 (9)	0.0039 (10)
C21	0.0270 (11)	0.0298 (11)	0.0405 (12)	−0.0017 (9)	0.0118 (9)	0.0034 (9)
C22	0.0293 (11)	0.0332 (12)	0.0515 (14)	−0.0003 (9)	0.0128 (10)	0.0035 (10)
C23	0.0375 (13)	0.0414 (13)	0.0639 (16)	0.0083 (11)	0.0233 (12)	0.0014 (12)
C24	0.0509 (15)	0.0520 (15)	0.0535 (15)	0.0090 (12)	0.0278 (13)	−0.0039 (13)
C25	0.0454 (13)	0.0492 (14)	0.0395 (12)	0.0066 (11)	0.0186 (11)	−0.0003 (11)
C26	0.0337 (12)	0.0450 (14)	0.0580 (16)	0.0089 (11)	0.0073 (11)	0.0098 (12)
C27	0.0426 (14)	0.0561 (16)	0.0428 (13)	0.0062 (12)	0.0040 (11)	0.0097 (13)

Geometric parameters (Å, º) top

Co1—O2	2.078 (2)	C9—C10	1.406 (3)
Co1—N4	2.155 (2)	C10—C11	1.392 (4)
Co1—N3	2.161 (2)	C10—C14	1.431 (3)
Co1—N2	2.172 (2)	C11—C12	1.367 (4)
Co1—N1	2.190 (2)	C11—H11	0.9300
Co1—Cl4	2.3985 (6)	C12—C13	1.386 (3)
N1—C4	1.320 (3)	C12—H12	0.9300
N1—C8	1.355 (3)	C13—H13	0.9300
N2—C13	1.316 (3)	C14—C15	1.340 (4)
N2—C9	1.356 (3)	C14—H14	0.9300
N3—C25	1.321 (3)	C15—H15	0.9300
N3—C21	1.356 (3)	C16—C17	1.394 (3)
N4—C16	1.320 (3)	C16—H16	0.9300
N4—C20	1.352 (3)	C17—C18	1.355 (4)
O1—C2	1.199 (3)	C17—H17	0.9300
O2—C2	1.240 (3)	C18—C19	1.405 (4)
Cl1—C1	1.658 (6)	C18—H18	0.9300
Cl2—C1	1.75 (5)	C19—C20	1.405 (3)
Cl3—C1	1.72 (2)	C19—C27	1.435 (4)
Cl1'—C1	1.822 (3)	C20—C21	1.436 (3)
Cl2'—C1	1.766 (11)	C21—C22	1.403 (3)
Cl3'—C1	1.770 (4)	C22—C23	1.398 (3)
C1—C2	1.569 (3)	C22—C26	1.436 (3)
C4—C5	1.395 (3)	C23—C24	1.355 (4)
C4—H4	0.9300	C23—H23	0.9300
C5—C6	1.359 (4)	C24—C25	1.400 (3)
C5—H5	0.9300	C24—H24	0.9300
C6—C7	1.390 (4)	C25—H25	0.9300
C6—H6	0.9300	C26—C27	1.346 (4)
C7—C8	1.415 (3)	C26—H26	0.9300
C7—C15	1.439 (3)	C27—H27	0.9300
C8—C9	1.432 (3)

O2—Co1—N4	84.70 (6)	N2—C9—C10	122.7 (2)
O2—Co1—N3	104.56 (6)	N2—C9—C8	117.34 (19)
N4—Co1—N3	76.40 (7)	C10—C9—C8	120.0 (2)
O2—Co1—N2	157.18 (6)	C11—C10—C9	117.6 (2)
N4—Co1—N2	87.28 (7)	C11—C10—C14	123.7 (2)
N3—Co1—N2	94.21 (7)	C9—C10—C14	118.8 (2)
O2—Co1—N1	84.80 (6)	C12—C11—C10	119.2 (2)
N4—Co1—N1	100.27 (7)	C12—C11—H11	120.4
N3—Co1—N1	169.56 (7)	C10—C11—H11	120.4
N2—Co1—N1	75.65 (7)	C11—C12—C13	119.4 (2)
O2—Co1—Cl4	97.77 (5)	C11—C12—H12	120.3
N4—Co1—Cl4	168.35 (5)	C13—C12—H12	120.3
N3—Co1—Cl4	91.98 (5)	N2—C13—C12	123.4 (2)
N2—Co1—Cl4	94.39 (5)	N2—C13—H13	118.3
N1—Co1—Cl4	91.31 (5)	C12—C13—H13	118.3
C4—N1—C8	117.74 (19)	C15—C14—C10	121.6 (2)
C4—N1—Co1	127.80 (15)	C15—C14—H14	119.2
C8—N1—Co1	114.18 (14)	C10—C14—H14	119.2
C13—N2—C9	117.68 (19)	C14—C15—C7	121.3 (2)
C13—N2—Co1	127.44 (15)	C14—C15—H15	119.3
C9—N2—Co1	114.68 (14)	C7—C15—H15	119.3
C25—N3—C21	117.66 (19)	N4—C16—C17	122.7 (2)
C25—N3—Co1	127.58 (15)	N4—C16—H16	118.7
C21—N3—Co1	114.71 (14)	C17—C16—H16	118.7
C16—N4—C20	118.3 (2)	C18—C17—C16	119.2 (2)
C16—N4—Co1	126.95 (16)	C18—C17—H17	120.4
C20—N4—Co1	114.59 (14)	C16—C17—H17	120.4
C2—O2—Co1	129.44 (15)	C17—C18—C19	120.3 (2)
C2—C1—Cl1	110.4 (3)	C17—C18—H18	119.9
C2—C1—Cl3	107.9 (8)	C19—C18—H18	119.9
Cl1—C1—Cl3	104.0 (7)	C20—C19—C18	116.4 (2)
C2—C1—Cl2	105.5 (12)	C20—C19—C27	119.0 (2)
Cl1—C1—Cl2	123.8 (18)	C18—C19—C27	124.7 (2)
Cl3—C1—Cl2	104.3 (15)	N4—C20—C19	123.0 (2)
C2—C1—Cl2'	110.8 (3)	N4—C20—C21	117.54 (19)
C2—C1—Cl3'	113.3 (2)	C19—C20—C21	119.4 (2)
Cl2'—C1—Cl3'	108.8 (3)	N3—C21—C22	123.0 (2)
C2—C1—Cl1'	108.47 (17)	N3—C21—C20	116.70 (18)
Cl2'—C1—Cl1'	105.7 (4)	C22—C21—C20	120.3 (2)
Cl3'—C1—Cl1'	109.5 (2)	C23—C22—C21	117.4 (2)
O1—C2—O2	130.7 (2)	C23—C22—C26	123.7 (2)
O1—C2—C1	117.5 (2)	C21—C22—C26	118.9 (2)
O2—C2—C1	111.7 (2)	C24—C23—C22	119.5 (2)
N1—C4—C5	123.0 (2)	C24—C23—H23	120.3
N1—C4—H4	118.5	C22—C23—H23	120.3
C5—C4—H4	118.5	C23—C24—C25	119.6 (2)
C6—C5—C4	119.7 (2)	C23—C24—H24	120.2
C6—C5—H5	120.2	C25—C24—H24	120.2
C4—C5—H5	120.2	N3—C25—C24	122.9 (2)
C5—C6—C7	119.6 (2)	N3—C25—H25	118.6
C5—C6—H6	120.2	C24—C25—H25	118.6
C7—C6—H6	120.2	C27—C26—C22	120.9 (2)
C6—C7—C8	117.2 (2)	C27—C26—H26	119.5
C6—C7—C15	124.4 (2)	C22—C26—H26	119.5
C8—C7—C15	118.4 (2)	C26—C27—C19	121.5 (2)
N1—C8—C7	122.8 (2)	C26—C27—H27	119.3
N1—C8—C9	117.28 (18)	C19—C27—H27	119.3
C7—C8—C9	119.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2ⁱ	0.93	2.54	3.364 (3)	148
C11—H11···Cl4ⁱⁱ	0.93	2.73	3.548 (2)	148
C23—H23···O1ⁱⁱⁱ	0.93	2.42	3.249 (3)	149

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

Experimental details

Crystal data
Chemical formula	[Co(C₂Cl₃O₂)Cl(C₁₂H₈N₂)₂]
M_r	617.16
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	18.2170 (6), 10.4612 (4), 14.6638 (7)
β (°)	112.685 (1)
V (Å³)	2578.32 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.12
Crystal size (mm)	0.26 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2005)
T_min, T_max	0.760, 0.824
No. of measured, independent and observed [I > 2σ(I)] reflections	13155, 4536, 3821
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.086, 1.01
No. of reflections	4536
No. of parameters	344
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.62

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Co1—O2	2.078 (2)	Co1—N2	2.172 (2)
Co1—N4	2.155 (2)	Co1—N1	2.190 (2)
Co1—N3	2.161 (2)	Co1—Cl4	2.3985 (6)

References

Bruker (2005). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, L., Wang, X.-W., Chen, F.-P., Chen, Y. & Chen, J.-Z. (2006). Acta Cryst. E62, m1743–m1745. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2005). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar