(Amino­acetato-κ2O,N)bis­(quinolin-8-olato-κ2O,N)cobalt(III) methanol solvate

Jing, B.-Q.; Meng, S.-M.; Han, J.; Wang, B.; Li, X.-M.

doi:10.1107/S1600536808013135

(Aminoacetato-κ²O,N)bis(quinolin-8-olato-κ²O,N)cobalt(III) methanol solvate

B.-Q. Jing, S.-M. Meng, J. Han, B. Wang and X.-M. Li

In the crystal structure of the title compound, [Co(C₂H₄NO₂)(C₉H₆NO)₂]·CH₃OH, the Co^III atom is chelated by two quinolin-8-olate and one glycinate anions in a distorted octahedral coordination geometry. The five-membered chelating glycinate ring assumes an envelope conformation. The complex molecules are assembled by intermolecular N—H

O hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808013135/xu2418sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808013135/xu2418Isup2.hkl Contains datablock I

CCDC reference: 661632

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.003 Å
R factor = 0.029
wR factor = 0.094
Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    --  N1      ..       5.53 su
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)         40 Ang.
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT180_ALERT_4_C Check Cell Rounding: # of Values Ending with 0 =          3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The 8–hydroxyquinoline (HQ) is a very good ligand, forms complex compounds with various metal ions in solution. The strong chelating action of HQ in solution has been extensively studied and widely used in analytical chemistry. In this work, we use glycin and 8–hydroxyquinoline as bidedtate ligand to synthesize the title complex, (I).

The molecular structure of the title compound is shown in Fig. 1. The Co^III atom is chelated by two 8-hydroxyquinoline and one glycin anions in a distorted octahedral coordination geometry. The Co—N bond distances are longer than Co—O bond distances (Table 1), which agrees with that found in a related structure, tris(8-quinolinolato)-cobalt(III) methanol solvate (Li et al. 2003). The two 8-hydroxyquinolate rings are almost perpendicular to each other with a dihedral angle of 81.0°. The five-membered chelating ring of the glycin assumes an envelope conformation, with N3 atom at the flap position. The complex molecules are assembled by intermolecular N–H···O hydrogen bonding (Table 2). Lattice methanol molecule is linked with complex via O—H···O and N—H···O hydrogen bonding (Fig. 2).

Related literature top

For a related structure, see: Li et al. (2003).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The atomic labeling scheme of (I) with displacement ellipsoids at the 30% probability level.
	Fig. 2. A packing diagram of the unit cell showing hydrogen bonds as dashed lines. H atoms, except for those involved in hydrogen bonds, are not included.
	Fig. 3. Interactive view of the complex.

(Aminoacetato-κ²O,N)bis(quinolin-8-olato- κ²O,N)cobalt(III) methanol solvate top

Crystal data top

[Co(C₂H₄NO₂)(C₉H₆NO)₂]·CH₄O	Z = 2
M_r = 453.33	F(000) = 468
Triclinic, P1	D_x = 1.522 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8377 (4) Å	Cell parameters from 7882 reflections
b = 10.6526 (4) Å	θ = 2.4–28.2°
c = 10.7369 (4) Å	µ = 0.91 mm⁻¹
α = 82.047 (1)°	T = 273 K
β = 76.289 (1)°	Block, purple
γ = 64.941 (1)°	0.20 × 0.15 × 0.12 mm
V = 989.32 (7) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3486 independent reflections
Radiation source: fine-focus sealed tube	3261 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→11
T_min = 0.840, T_max = 0.899	k = −12→12
11346 measured reflections	l = −12→12

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.073P)² + 0.17P] where P = (F_o² + 2F_c²)/3
3486 reflections	(Δ/σ)_max = 0.001
281 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Co(C₂H₄NO₂)(C₉H₆NO)₂]·CH₄O	γ = 64.941 (1)°
M_r = 453.33	V = 989.32 (7) Å³
Triclinic, P1	Z = 2
a = 9.8377 (4) Å	Mo Kα radiation
b = 10.6526 (4) Å	µ = 0.91 mm⁻¹
c = 10.7369 (4) Å	T = 273 K
α = 82.047 (1)°	0.20 × 0.15 × 0.12 mm
β = 76.289 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3486 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3261 reflections with I > 2σ(I)
T_min = 0.840, T_max = 0.899	R_int = 0.017
11346 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.28 e Å⁻³
3486 reflections	Δρ_min = −0.36 e Å⁻³
281 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
Co1	0.21615 (2)	0.26369 (2)	0.46144 (2)	0.03237 (12)
O1	0.36577 (14)	0.20861 (13)	0.56554 (12)	0.0381 (3)
O2	0.46440 (17)	0.29619 (16)	0.67761 (14)	0.0553 (4)
O3	0.05933 (15)	0.33761 (13)	0.60596 (13)	0.0418 (3)
O4	0.06935 (14)	0.32742 (13)	0.35430 (13)	0.0421 (3)
O5	0.4828 (3)	0.4912 (3)	0.2562 (2)	0.1083 (9)
H5	0.4933	0.5573	0.2770	0.162*
N1	0.18775 (16)	0.09298 (15)	0.50938 (14)	0.0348 (3)
N2	0.36569 (17)	0.19377 (15)	0.30857 (14)	0.0349 (3)
N3	0.23374 (19)	0.43960 (16)	0.43835 (17)	0.0397 (4)
C1	0.0225 (2)	0.23999 (19)	0.67578 (17)	0.0391 (4)
C2	−0.0769 (2)	0.2598 (2)	0.7924 (2)	0.0539 (5)
H2	−0.1231	0.3465	0.8279	0.065*
C3	−0.1088 (3)	0.1483 (3)	0.8583 (2)	0.0683 (7)
H3	−0.1735	0.1626	0.9386	0.082*
C4	−0.0487 (3)	0.0206 (3)	0.8091 (2)	0.0656 (6)
H4	−0.0744	−0.0498	0.8543	0.079*
C5	0.0530 (2)	−0.0043 (2)	0.6888 (2)	0.0460 (5)
C6	0.1205 (2)	−0.1297 (2)	0.6232 (2)	0.0528 (5)
H6	0.0999	−0.2057	0.6600	0.063*
C7	0.2144 (2)	−0.1391 (2)	0.5076 (2)	0.0504 (5)
H7	0.2567	−0.2210	0.4642	0.060*
C8	0.2488 (2)	−0.02614 (18)	0.45221 (19)	0.0413 (4)
H8	0.3162	−0.0354	0.3735	0.050*
C9	0.08930 (19)	0.10617 (18)	0.62504 (17)	0.0364 (4)
C10	0.1360 (2)	0.30635 (18)	0.23300 (19)	0.0422 (4)
C11	0.0622 (3)	0.3473 (2)	0.1301 (2)	0.0590 (6)
H11	−0.0435	0.3965	0.1439	0.071*
C12	0.1463 (4)	0.3150 (3)	0.0052 (2)	0.0690 (7)
H12	0.0939	0.3445	−0.0622	0.083*
C13	0.3015 (4)	0.2421 (3)	−0.0224 (2)	0.0657 (7)
H13	0.3530	0.2230	−0.1068	0.079*
C14	0.3826 (3)	0.1964 (2)	0.07908 (19)	0.0500 (5)
C15	0.5417 (3)	0.1158 (2)	0.0668 (2)	0.0576 (5)
H15	0.6026	0.0903	−0.0139	0.069*
C16	0.6059 (2)	0.0755 (2)	0.1726 (2)	0.0558 (5)
H16	0.7101	0.0205	0.1645	0.067*
C17	0.5149 (2)	0.1171 (2)	0.29365 (19)	0.0438 (4)
H17	0.5602	0.0904	0.3653	0.053*
C18	0.2987 (2)	0.23139 (18)	0.20409 (18)	0.0393 (4)
C19	0.3819 (2)	0.31043 (19)	0.60261 (16)	0.0392 (4)
C20	0.2899 (2)	0.45316 (19)	0.5487 (2)	0.0452 (4)
H20A	0.2040	0.5039	0.6144	0.054*
H20B	0.3538	0.5047	0.5221	0.054*
C21	0.5849 (6)	0.4394 (5)	0.1517 (4)	0.1377 (19)
H21A	0.5343	0.4321	0.0885	0.207*
H21B	0.6579	0.3490	0.1722	0.207*
H21C	0.6367	0.4993	0.1183	0.207*
H22	0.143 (3)	0.502 (3)	0.436 (2)	0.060 (7)*
H21	0.295 (3)	0.444 (2)	0.369 (2)	0.048 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.02705 (16)	0.02604 (16)	0.04380 (17)	−0.01193 (11)	−0.00651 (10)	0.00211 (10)
O1	0.0359 (7)	0.0324 (7)	0.0464 (7)	−0.0132 (5)	−0.0107 (5)	−0.0006 (5)
O2	0.0585 (9)	0.0602 (9)	0.0529 (8)	−0.0229 (7)	−0.0185 (7)	−0.0116 (7)
O3	0.0365 (7)	0.0317 (6)	0.0529 (7)	−0.0144 (5)	0.0006 (5)	−0.0027 (5)
O4	0.0315 (6)	0.0366 (7)	0.0594 (8)	−0.0142 (5)	−0.0147 (6)	0.0056 (6)
O5	0.1061 (17)	0.1167 (19)	0.1255 (19)	−0.0846 (16)	0.0328 (15)	−0.0453 (15)
N1	0.0294 (7)	0.0310 (7)	0.0468 (8)	−0.0139 (6)	−0.0126 (6)	0.0036 (6)
N2	0.0330 (8)	0.0318 (7)	0.0431 (8)	−0.0165 (6)	−0.0089 (6)	0.0020 (6)
N3	0.0316 (8)	0.0305 (8)	0.0567 (10)	−0.0144 (7)	−0.0078 (7)	0.0035 (7)
C1	0.0321 (9)	0.0415 (10)	0.0468 (10)	−0.0187 (7)	−0.0087 (7)	0.0023 (8)
C2	0.0489 (12)	0.0610 (13)	0.0523 (11)	−0.0273 (10)	0.0013 (9)	−0.0072 (10)
C3	0.0685 (15)	0.0868 (18)	0.0532 (12)	−0.0460 (14)	0.0061 (11)	0.0020 (12)
C4	0.0710 (15)	0.0741 (16)	0.0641 (14)	−0.0506 (13)	−0.0070 (12)	0.0173 (12)
C5	0.0414 (10)	0.0463 (11)	0.0589 (11)	−0.0272 (9)	−0.0163 (9)	0.0131 (9)
C6	0.0506 (11)	0.0379 (10)	0.0813 (15)	−0.0285 (9)	−0.0242 (11)	0.0152 (9)
C7	0.0458 (11)	0.0330 (9)	0.0788 (14)	−0.0189 (8)	−0.0193 (10)	−0.0011 (9)
C8	0.0377 (9)	0.0336 (9)	0.0547 (11)	−0.0146 (7)	−0.0135 (8)	−0.0003 (8)
C9	0.0310 (9)	0.0374 (9)	0.0461 (9)	−0.0185 (7)	−0.0135 (7)	0.0070 (7)
C10	0.0461 (10)	0.0310 (9)	0.0590 (12)	−0.0226 (8)	−0.0218 (9)	0.0108 (8)
C11	0.0656 (14)	0.0484 (12)	0.0783 (15)	−0.0302 (11)	−0.0415 (12)	0.0196 (11)
C12	0.101 (2)	0.0613 (15)	0.0661 (15)	−0.0430 (15)	−0.0491 (15)	0.0208 (12)
C13	0.104 (2)	0.0626 (14)	0.0471 (12)	−0.0481 (15)	−0.0239 (12)	0.0099 (10)
C14	0.0691 (14)	0.0482 (12)	0.0451 (10)	−0.0369 (11)	−0.0115 (10)	0.0026 (9)
C15	0.0618 (14)	0.0653 (14)	0.0516 (12)	−0.0374 (11)	0.0071 (10)	−0.0148 (10)
C16	0.0408 (11)	0.0627 (13)	0.0630 (13)	−0.0224 (10)	0.0013 (9)	−0.0159 (10)
C17	0.0340 (9)	0.0455 (10)	0.0523 (10)	−0.0160 (8)	−0.0078 (8)	−0.0051 (8)
C18	0.0472 (10)	0.0330 (9)	0.0463 (10)	−0.0241 (8)	−0.0143 (8)	0.0062 (7)
C19	0.0337 (9)	0.0423 (10)	0.0383 (9)	−0.0145 (8)	0.0010 (7)	−0.0084 (7)
C20	0.0412 (10)	0.0362 (9)	0.0614 (12)	−0.0182 (8)	−0.0087 (9)	−0.0070 (8)
C21	0.197 (5)	0.142 (4)	0.116 (3)	−0.129 (4)	0.030 (3)	−0.047 (3)

Geometric parameters (Å, º) top

Co1—O1	1.9045 (12)	C5—C6	1.417 (3)
Co1—O3	1.8926 (13)	C6—C7	1.348 (3)
Co1—O4	1.9002 (13)	C6—H6	0.9300
Co1—N1	1.9373 (14)	C7—C8	1.403 (3)
Co1—N2	1.9179 (15)	C7—H7	0.9300
Co1—N3	1.9309 (15)	C8—H8	0.9300
O1—C19	1.287 (2)	C10—C11	1.384 (3)
O2—C19	1.225 (2)	C10—C18	1.431 (3)
O3—C1	1.323 (2)	C11—C12	1.400 (4)
O4—C10	1.314 (2)	C11—H11	0.9300
O5—C21	1.319 (4)	C12—C13	1.367 (4)
O5—H5	0.8200	C12—H12	0.9300
N1—C8	1.320 (2)	C13—C14	1.413 (3)
N1—C9	1.365 (2)	C13—H13	0.9300
N2—C17	1.326 (2)	C14—C18	1.405 (3)
N2—C18	1.362 (2)	C14—C15	1.413 (3)
N3—C20	1.468 (3)	C15—C16	1.361 (3)
N3—H22	0.86 (3)	C15—H15	0.9300
N3—H21	0.85 (2)	C16—C17	1.399 (3)
C1—C2	1.374 (3)	C16—H16	0.9300
C1—C9	1.419 (3)	C17—H17	0.9300
C2—C3	1.410 (3)	C19—C20	1.518 (3)
C2—H2	0.9300	C20—H20A	0.9700
C3—C4	1.359 (4)	C20—H20B	0.9700
C3—H3	0.9300	C21—H21A	0.9600
C4—C5	1.414 (3)	C21—H21B	0.9600
C4—H4	0.9300	C21—H21C	0.9600
C5—C9	1.414 (2)

O3—Co1—O4	90.60 (6)	C6—C7—H7	119.8
O3—Co1—O1	89.93 (6)	C8—C7—H7	119.8
O4—Co1—O1	176.81 (5)	N1—C8—C7	121.45 (18)
O3—Co1—N2	176.47 (5)	N1—C8—H8	119.3
O4—Co1—N2	85.88 (6)	C7—C8—H8	119.3
O1—Co1—N2	93.56 (6)	N1—C9—C5	122.64 (17)
O3—Co1—N3	87.07 (7)	N1—C9—C1	115.27 (15)
O4—Co1—N3	91.14 (6)	C5—C9—C1	122.07 (17)
O1—Co1—N3	85.75 (6)	O4—C10—C11	125.8 (2)
N2—Co1—N3	92.71 (7)	O4—C10—C18	117.56 (16)
O3—Co1—N1	85.82 (6)	C11—C10—C18	116.6 (2)
O4—Co1—N1	92.39 (6)	C10—C11—C12	120.2 (2)
O1—Co1—N1	90.79 (6)	C10—C11—H11	119.9
N2—Co1—N1	94.60 (6)	C12—C11—H11	119.9
N3—Co1—N1	172.09 (7)	C13—C12—C11	123.2 (2)
C19—O1—Co1	113.96 (11)	C13—C12—H12	118.4
C1—O3—Co1	111.40 (11)	C11—C12—H12	118.4
C10—O4—Co1	111.26 (11)	C12—C13—C14	119.0 (2)
C21—O5—H5	109.5	C12—C13—H13	120.5
C8—N1—C9	119.18 (15)	C14—C13—H13	120.5
C8—N1—Co1	131.33 (13)	C18—C14—C13	117.7 (2)
C9—N1—Co1	109.46 (12)	C18—C14—C15	116.45 (19)
C17—N2—C18	119.37 (17)	C13—C14—C15	125.8 (2)
C17—N2—Co1	129.99 (13)	C16—C15—C14	120.2 (2)
C18—N2—Co1	110.63 (12)	C16—C15—H15	119.9
C20—N3—Co1	107.24 (11)	C14—C15—H15	119.9
C20—N3—H22	111.7 (16)	C15—C16—C17	119.9 (2)
Co1—N3—H22	106.0 (17)	C15—C16—H16	120.1
C20—N3—H21	110.4 (15)	C17—C16—H16	120.1
Co1—N3—H21	111.4 (15)	N2—C17—C16	121.50 (18)
H22—N3—H21	110 (2)	N2—C17—H17	119.3
O3—C1—C2	124.64 (18)	C16—C17—H17	119.3
O3—C1—C9	117.25 (15)	N2—C18—C14	122.54 (18)
C2—C1—C9	118.10 (17)	N2—C18—C10	114.32 (17)
C1—C2—C3	119.9 (2)	C14—C18—C10	123.13 (18)
C1—C2—H2	120.1	O2—C19—O1	123.35 (17)
C3—C2—H2	120.1	O2—C19—C20	120.82 (17)
C4—C3—C2	122.5 (2)	O1—C19—C20	115.83 (15)
C4—C3—H3	118.7	N3—C20—C19	109.90 (15)
C2—C3—H3	118.7	N3—C20—H20A	109.7
C3—C4—C5	119.62 (19)	C19—C20—H20A	109.7
C3—C4—H4	120.2	N3—C20—H20B	109.7
C5—C4—H4	120.2	C19—C20—H20B	109.7
C4—C5—C9	117.7 (2)	H20A—C20—H20B	108.2
C4—C5—C6	126.22 (19)	O5—C21—H21A	109.5
C9—C5—C6	116.04 (18)	O5—C21—H21B	109.5
C7—C6—C5	120.19 (17)	H21A—C21—H21B	109.5
C7—C6—H6	119.9	O5—C21—H21C	109.5
C5—C6—H6	119.9	H21A—C21—H21C	109.5
C6—C7—C8	120.45 (19)	H21B—C21—H21C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O2ⁱ	0.82	1.92	2.743 (3)	175
N3—H21···O5	0.85 (2)	2.17 (3)	2.950 (3)	153 (2)
N3—H22···O3ⁱⁱ	0.86 (3)	2.10 (3)	2.952 (2)	169 (2)

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

Experimental details

Crystal data
Chemical formula	[Co(C₂H₄NO₂)(C₉H₆NO)₂]·CH₄O
M_r	453.33
Crystal system, space group	Triclinic, P1
Temperature (K)	273
a, b, c (Å)	9.8377 (4), 10.6526 (4), 10.7369 (4)
α, β, γ (°)	82.047 (1), 76.289 (1), 64.941 (1)
V (Å³)	989.32 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.91
Crystal size (mm)	0.20 × 0.15 × 0.12

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.840, 0.899
No. of measured, independent and observed [I > 2σ(I)] reflections	11346, 3486, 3261
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.094, 1.00
No. of reflections	3486
No. of parameters	281
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.36

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Co1—O1	1.9045 (12)	Co1—N1	1.9373 (14)
Co1—O3	1.8926 (13)	Co1—N2	1.9179 (15)
Co1—O4	1.9002 (13)	Co1—N3	1.9309 (15)

O3—Co1—O4	90.60 (6)	O1—Co1—N3	85.75 (6)
O3—Co1—O1	89.93 (6)	N2—Co1—N3	92.71 (7)
O4—Co1—O1	176.81 (5)	O3—Co1—N1	85.82 (6)
O3—Co1—N2	176.47 (5)	O4—Co1—N1	92.39 (6)
O4—Co1—N2	85.88 (6)	O1—Co1—N1	90.79 (6)
O1—Co1—N2	93.56 (6)	N2—Co1—N1	94.60 (6)
O3—Co1—N3	87.07 (7)	N3—Co1—N1	172.09 (7)
O4—Co1—N3	91.14 (6)