Bis(μ-3,5-dinitro-2-oxidobenzoato)-κ³O¹,O²:O¹;κ³O¹:O¹,O²-bis[aqua­(2-phenyl-1,3,7,8-tetra­azacyclo­penta­[l]phenanthrene-κ²N⁷,N⁸)cobalt(II)]

In the title compound, [Co₂(C₇H₂N₂O₇)₂(C₁₉H₁₂N₄)₂(H₂O)₂], the Co^II atom is six-coordinated by two N atoms from a 2-phenyl-1H-1,3,7,8,-tetraaza­cyclo­penta­[l]phenanthrene (L) ligand, three O atoms from two 3,5-dinitro-2-oxidobenzoate (3,5-dinitro­salicylate or DNSA) ligands and one O atom from a water mol­ecule in a distorted octa­hedral geometry. The Co^II atoms are bridged by two carboxyl­ate O atoms from two DNSA ligands, forming a centrosymmetric dinuclear structure. Neighbouring dinuclear units inter­act with each other through two types of π–π inter­actions between the L ligands [shortest centroid–centroid distance = 3.646 (3) Å] and between the L and DNSA ligands [shortest atom-to-centroid distance = 3.794 (3) Å]. N—H...O, O—H...N and O—H...O hydrogen bonds are observed, which lead to a three-dimensional structure.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.044
• wR factor = 0.111
• Data-to-parameter ratio = 10.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT910_ALERT_3_B Missing # of FCF Reflections Below Th(Min) .....         21

Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co     --  O1_a    ..       6.38 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N6
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.10
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595          8

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......        168
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)        400 Deg.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          3

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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

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S1. Comment

Metal-organic coordination polymers have attracted increasing interest over the past decade because of their intriguing structures and tremendous potential applications in catalysis, molecular adsorption, nonlinear optics, magnetism, and so on (Che et al., 2008). 1,10-Phenanthroline (phen) has been widely used to build supramolecular architectures owing to its excellent coordinating ability and large conjugated system. However, building blocks derived from the appropriate modification of phen, such as 2-phenyl-1H-1,3,7,8-tetra-azacyclopenta[l]phenanthrene (L) have received considerably less attention (Liu et al., 2009). Hereby, we have prepared the title compound based on L and 3,5-dinitrosalicylic acid (H₂DNSA) ligands.

In the title compound, the Co^II atom is six-coordinated by two N atoms from one L ligand, four O atoms from two DNSA ligands and one water molecule (Fig. 1). The Co—O distances range from 1.991 (3) to 2.216 (3) Å and the Co—N lengths are 2.095 (3) and 2.102 (3) Å (Table 1). The N1, N2, O1, O3 atoms comprise the equatorial plane, while the O1ⁱ and OW1 atoms occupy the axial position [symmetry code: (i) -x, -y, 1-z]. A carboxylate O atom and the hydroxy O atom of the DNSA ligand coordinate to one Co atom, and this carboxylate O atom bridges the other Co atom, forming a dinuclear structure. The two nitro groups are uncoordinated.

It is noteworthy that various hydrogen bonds interactions are observed in the title compound. (a) An N—H···O hydrogen bond between the imidazole ring donor and the nitro group of the DNSA ligand (Table 2). (b) O—H···N or O—H···O hydrogen bonds involving the coordinated water molecule OW1 and the imidazole N3 and carboxylate O2 atoms (Table 2). In addition, two types of π–π stacking interactions further intensify the architectures. One is the offset face-to-face π–π interactions between the L ligands with the shortest centroid–centroid distance of 3.646 (3) Å, while the other exists between the L and DNSA ligands [shortest atom-to-centroid distance = 3.794 (3) Å] (Fig. 2), which lead to a three-dimensional supramolecular structure (Fig. 3).

Related literature

For general background to metal–organic coordination polymers, see: Che et al. (2008). For a related structure, see: Liu et al. (2009). For the ligand synthesis, see: Steck & Day (1943).

S2. Experimental

The L ligand was synthesized according to the literature method (Steck & Day, 1943). The title compound was synthesized under hydrothermal conditions. A mixture of L (0.06 g, 0.2 mmol), H₂DNSA (0.048 g, 0.2 mmol), Co(NO₃)₂ (0.036 g, 0.2 mmol) and water (10 ml) in a mole ratio 1:1:1:5000 was placed in a 25 ml Teflon-lined autoclave and heated for 3 d at 433 K under autogenous pressure. Upon cooling and opening the bomb, yellow block-shaped crystals were obtained, washed with H₂O and dried in air (yield 45% based on Co).

S3. Refinement

H atoms on C and N atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 and N—H = 0.86 Å and with U_iso(H) = 1.2U_eq(C,N). H atoms of water molecule were located from a difference Fourier map and their positions and U_iso values were refined freely.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [Symmetry code: (A) -x, -y, -z+1.]
	Fig. 2. View of the one-dimensional supramolecular chain generated by π–π interactions (dashed lines). H atoms except those of water molecules have been omitted for clarity.
	Fig. 3. View of a three-dimensional supramolecular structure with hydrogen bonds indicated by dotted lines. Most H atoms have been omitted.

Bis(µ-3,5-dinitro-2-oxidobenzoato)-κ³O¹,O²:O¹;κ³O¹:O¹,O²- bis[aqua(2-phenyl-1,3,7,8-tetraazacyclopenta[l]phenanthrene- κ²N⁷,N⁸)cobalt(II)]

Crystal data

[Co2(C7H2N2O7)2(C19H12N4)2(H2O)2]	Z = 1
Mr = 1198.76	F(000) = 610
Triclinic, P1	Dx = 1.722 Mg m^−3 Dm = 1.722 Mg m^−3 Dm measured by not measured
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2943 (4) Å	Cell parameters from 3653 reflections
b = 11.0232 (5) Å	θ = 4.4–25°
c = 13.6139 (7) Å	µ = 0.81 mm^−1
α = 102.690 (4)°	T = 292 K
β = 107.282 (4)°	Block, yellow
γ = 90.459 (4)°	0.32 × 0.27 × 0.23 mm
V = 1155.9 (1) Å^3

Data collection

Oxford Diffraction Gemini R Ultra CCD diffractometer	4041 independent reflections
Radiation source: fine-focus sealed tube	2933 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω scans	θmax = 25.0°, θmin = 4.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	h = −9→9
Tmin = 0.771, Tmax = 0.829	k = −13→11
7153 measured reflections	l = −14→16

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0638P)^2] where P = (Fo^2 + 2Fc^2)/3
4041 reflections	(Δ/σ)max = 0.002
378 parameters	Δρmax = 0.97 e Å^−3
168 restraints	Δρmin = −1.00 e Å^−3

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

	x	y	z	Uiso*/Ueq
C1	−0.0231 (5)	0.3815 (4)	0.6428 (3)	0.0304 (9)
H1	0.0452	0.3635	0.7049	0.037*
C2	−0.1233 (6)	0.4828 (4)	0.6499 (3)	0.0346 (10)
H2	−0.1214	0.5307	0.7157	0.041*
C3	−0.2237 (5)	0.5105 (4)	0.5595 (3)	0.0336 (9)
H3	−0.2911	0.5774	0.5631	0.040*
C4	−0.2245 (5)	0.4375 (4)	0.4614 (3)	0.0286 (8)
C5	−0.3250 (5)	0.4543 (4)	0.3592 (3)	0.0299 (8)
C6	−0.3182 (5)	0.3757 (4)	0.2679 (3)	0.0311 (9)
C7	−0.2138 (5)	0.2745 (4)	0.2631 (3)	0.0277 (8)
C8	−0.1991 (5)	0.1923 (4)	0.1726 (3)	0.0344 (9)
H8	−0.2600	0.2020	0.1058	0.041*
C9	−0.0946 (6)	0.0974 (4)	0.1829 (3)	0.0369 (10)
H9	−0.0838	0.0422	0.1233	0.044*
C10	−0.0049 (5)	0.0841 (4)	0.2834 (3)	0.0325 (9)
H10	0.0650	0.0189	0.2895	0.039*
C11	−0.1165 (5)	0.2559 (4)	0.3627 (3)	0.0247 (8)
C12	−0.1215 (5)	0.3373 (3)	0.4607 (3)	0.0249 (8)
C13	−0.4998 (5)	0.5157 (4)	0.2329 (3)	0.0322 (9)
C14	−0.6334 (5)	0.5801 (4)	0.1703 (3)	0.0356 (9)
C15	−0.6963 (6)	0.6831 (4)	0.2208 (4)	0.0438 (11)
H15	−0.6518	0.7137	0.2935	0.053*
C16	−0.8264 (7)	0.7403 (5)	0.1618 (4)	0.0546 (13)
H16	−0.8696	0.8091	0.1957	0.066*
C17	−0.8916 (7)	0.6973 (5)	0.0553 (4)	0.0606 (14)
H17	−0.9787	0.7365	0.0167	0.073*
C18	−0.8286 (7)	0.5960 (6)	0.0052 (4)	0.0619 (15)
H18	−0.8723	0.5671	−0.0677	0.074*
C19	−0.7008 (7)	0.5364 (5)	0.0621 (4)	0.0511 (13)
H19	−0.6599	0.4668	0.0276	0.061*
C20	0.3815 (5)	−0.0284 (4)	0.6442 (3)	0.0269 (8)
C21	0.5087 (5)	−0.0973 (4)	0.6896 (3)	0.0328 (9)
H21	0.5419	−0.1637	0.6466	0.039*
C22	0.5884 (5)	−0.0697 (4)	0.7980 (3)	0.0368 (9)
C23	0.5475 (5)	0.0299 (4)	0.8637 (3)	0.0360 (9)
H23	0.6050	0.0499	0.9358	0.043*
C24	0.4202 (5)	0.0997 (4)	0.8213 (3)	0.0323 (9)
C25	0.3257 (5)	0.0739 (4)	0.7106 (3)	0.0265 (8)
C26	0.2996 (5)	−0.0712 (4)	0.5268 (3)	0.0271 (8)
N1	−0.0218 (4)	0.3109 (3)	0.5517 (2)	0.0254 (7)
N2	−0.0149 (4)	0.1606 (3)	0.3706 (2)	0.0250 (6)
N3	−0.4378 (4)	0.5429 (3)	0.3369 (3)	0.0324 (8)
N4	−0.4312 (4)	0.4167 (3)	0.1875 (3)	0.0321 (8)
H4	−0.4538	0.3850	0.1209	0.039*
N5	0.7161 (5)	−0.1487 (4)	0.8424 (3)	0.0484 (9)
N6	0.3854 (5)	0.2056 (4)	0.8942 (3)	0.0446 (9)
O1	0.1485 (3)	−0.0397 (2)	0.4865 (2)	0.0305 (5)
O2	0.3743 (4)	−0.1379 (3)	0.4735 (2)	0.0459 (8)
O3	0.2036 (4)	0.1369 (3)	0.6762 (2)	0.0339 (5)
O4	0.7338 (5)	−0.2469 (4)	0.7867 (3)	0.0650 (9)
O5	0.8033 (5)	−0.1117 (4)	0.9352 (3)	0.0691 (10)
O6	0.4661 (6)	0.2254 (4)	0.9869 (3)	0.0813 (11)
O7	0.2851 (6)	0.2779 (4)	0.8644 (3)	0.0857 (10)
OW1	0.3241 (4)	0.2215 (3)	0.5222 (3)	0.0345 (5)
Co	0.09090 (7)	0.14151 (5)	0.52610 (4)	0.0264 (2)
H1WA	0.362 (7)	0.285 (6)	0.566 (5)	0.064 (18)*
H1WB	0.407 (7)	0.184 (5)	0.523 (4)	0.058 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.034 (2)	0.031 (2)	0.0251 (15)	0.0072 (17)	0.0071 (17)	0.0072 (14)
C2	0.041 (3)	0.031 (2)	0.0312 (16)	0.0091 (18)	0.0129 (18)	0.0042 (17)
C3	0.032 (2)	0.031 (2)	0.0381 (15)	0.0114 (19)	0.0118 (18)	0.0079 (15)
C4	0.027 (2)	0.0249 (19)	0.0326 (12)	0.0062 (16)	0.0055 (16)	0.0089 (14)
C5	0.026 (2)	0.027 (2)	0.0351 (13)	0.0054 (16)	0.0042 (16)	0.0115 (14)
C6	0.027 (2)	0.035 (2)	0.0308 (14)	0.0071 (17)	0.0025 (16)	0.0133 (14)
C7	0.024 (2)	0.0286 (19)	0.0279 (13)	0.0026 (15)	0.0021 (15)	0.0094 (14)
C8	0.036 (3)	0.040 (2)	0.0254 (16)	0.0039 (18)	0.0045 (18)	0.0088 (15)
C9	0.040 (3)	0.041 (2)	0.0267 (14)	0.0078 (19)	0.0101 (18)	0.0022 (17)
C10	0.029 (2)	0.037 (2)	0.0295 (13)	0.0080 (19)	0.0082 (17)	0.0038 (15)
C11	0.020 (2)	0.0269 (19)	0.0264 (12)	0.0036 (15)	0.0042 (15)	0.0091 (13)
C12	0.021 (2)	0.0230 (18)	0.0279 (12)	0.0032 (15)	0.0026 (15)	0.0069 (13)
C13	0.031 (2)	0.030 (2)	0.0349 (14)	0.0058 (16)	0.0057 (16)	0.0121 (16)
C14	0.030 (2)	0.036 (2)	0.0398 (16)	0.0072 (17)	0.0048 (16)	0.0158 (16)
C15	0.044 (3)	0.036 (2)	0.049 (2)	0.011 (2)	0.008 (2)	0.0137 (18)
C16	0.048 (3)	0.047 (3)	0.072 (2)	0.021 (2)	0.014 (2)	0.025 (2)
C17	0.046 (3)	0.070 (3)	0.069 (2)	0.023 (3)	0.005 (2)	0.041 (2)
C18	0.058 (4)	0.074 (4)	0.045 (2)	0.015 (3)	−0.005 (2)	0.024 (2)
C19	0.050 (3)	0.059 (3)	0.0401 (16)	0.018 (2)	0.005 (2)	0.0139 (19)
C20	0.019 (2)	0.029 (2)	0.0318 (13)	0.0034 (15)	0.0040 (13)	0.0095 (14)
C21	0.025 (2)	0.035 (2)	0.0384 (15)	0.0094 (17)	0.0063 (16)	0.0134 (16)
C22	0.024 (2)	0.047 (2)	0.0400 (16)	0.0079 (18)	0.0040 (16)	0.0203 (16)
C23	0.027 (2)	0.051 (2)	0.0278 (19)	0.0026 (18)	−0.0005 (17)	0.0160 (16)
C24	0.025 (2)	0.042 (2)	0.0263 (13)	0.0014 (17)	0.0010 (14)	0.0089 (14)
C25	0.022 (2)	0.031 (2)	0.0252 (13)	0.0047 (15)	0.0029 (14)	0.0104 (13)
C26	0.0219 (17)	0.0223 (19)	0.0328 (14)	0.0051 (15)	0.0040 (12)	0.0035 (14)
N1	0.0257 (17)	0.0237 (14)	0.0258 (11)	0.0052 (13)	0.0052 (13)	0.0070 (11)
N2	0.0223 (16)	0.0260 (15)	0.0258 (10)	0.0044 (12)	0.0052 (12)	0.0071 (11)
N3	0.032 (2)	0.0288 (17)	0.0350 (13)	0.0090 (15)	0.0051 (15)	0.0109 (13)
N4	0.033 (2)	0.0336 (18)	0.0272 (14)	0.0092 (15)	0.0014 (14)	0.0112 (13)
N5	0.034 (2)	0.062 (2)	0.0523 (18)	0.0166 (19)	0.0058 (15)	0.0300 (15)
N6	0.041 (2)	0.057 (2)	0.0267 (13)	0.0099 (17)	0.0015 (15)	0.0037 (14)
O1	0.0280 (10)	0.0323 (9)	0.0278 (9)	0.0142 (9)	0.0037 (8)	0.0059 (8)
O2	0.0315 (15)	0.0534 (16)	0.0404 (14)	0.0173 (13)	0.0048 (12)	−0.0062 (12)
O3	0.0321 (11)	0.0361 (11)	0.0274 (8)	0.0156 (9)	0.0014 (8)	0.0050 (8)
O4	0.055 (2)	0.0667 (19)	0.0686 (19)	0.0307 (17)	0.0039 (16)	0.0270 (15)
O5	0.059 (2)	0.084 (2)	0.0569 (17)	0.0309 (18)	−0.0046 (14)	0.0289 (16)
O6	0.092 (2)	0.092 (2)	0.0308 (12)	0.0423 (19)	−0.0108 (15)	−0.0076 (15)
O7	0.0906 (19)	0.0901 (18)	0.0420 (14)	0.0503 (15)	−0.0127 (14)	−0.0113 (14)
OW1	0.0268 (11)	0.0354 (13)	0.0367 (13)	0.0091 (10)	0.0058 (10)	0.0039 (11)
Co	0.0251 (3)	0.0267 (3)	0.0236 (3)	0.0104 (2)	0.0015 (2)	0.0059 (2)

Geometric parameters (Å, º)

C1—N1	1.314 (5)	C17—C18	1.369 (8)
C1—C2	1.401 (5)	C17—H17	0.9300
C1—H1	0.9300	C18—C19	1.379 (6)
C2—C3	1.365 (6)	C18—H18	0.9300
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.398 (6)	C20—C21	1.379 (5)
C3—H3	0.9300	C20—C25	1.453 (5)
C4—C12	1.402 (5)	C20—C26	1.503 (6)
C4—C5	1.446 (5)	C21—C22	1.389 (6)
C5—C6	1.366 (6)	C21—H21	0.9300
C5—N3	1.377 (5)	C22—C23	1.368 (6)
C6—N4	1.376 (5)	C22—N5	1.454 (5)
C6—C7	1.420 (5)	C23—C24	1.373 (5)
C7—C8	1.398 (6)	C23—H23	0.9300
C7—C11	1.416 (5)	C24—C25	1.440 (5)
C8—C9	1.368 (6)	C24—N6	1.448 (5)
C8—H8	0.9300	C25—O3	1.265 (4)
C9—C10	1.389 (6)	C26—O2	1.220 (5)
C9—H9	0.9300	C26—O1	1.294 (4)
C10—N2	1.322 (5)	N4—H4	0.8600
C10—H10	0.9300	N5—O4	1.215 (5)
C11—N2	1.356 (5)	N5—O5	1.229 (5)
C11—C12	1.447 (5)	N6—O7	1.202 (5)
C12—N1	1.363 (5)	N6—O6	1.209 (5)
C13—N3	1.319 (5)	OW1—H1WA	0.81 (6)
C13—N4	1.349 (5)	OW1—H1WB	0.80 (5)
C13—C14	1.475 (5)	Co—N1	2.102 (3)
C14—C19	1.383 (6)	Co—N2	2.095 (3)
C14—C15	1.383 (6)	Co—O1	2.050 (2)
C15—C16	1.388 (6)	Co—O1^i	2.216 (3)
C15—H15	0.9300	Co—O3	1.991 (3)
C16—C17	1.359 (8)	Co—OW1	2.139 (3)
C16—H16	0.9300
N1—C1—C2	122.5 (4)	C21—C20—C26	116.4 (3)
N1—C1—H1	118.8	C25—C20—C26	123.5 (3)
C2—C1—H1	118.8	C20—C21—C22	121.5 (4)
C3—C2—C1	119.4 (4)	C20—C21—H21	119.3
C3—C2—H2	120.3	C22—C21—H21	119.3
C1—C2—H2	120.3	C23—C22—C21	121.1 (4)
C2—C3—C4	119.4 (4)	C23—C22—N5	119.6 (4)
C2—C3—H3	120.3	C21—C22—N5	119.3 (4)
C4—C3—H3	120.3	C22—C23—C24	118.9 (4)
C3—C4—C12	117.8 (3)	C22—C23—H23	120.6
C3—C4—C5	125.9 (3)	C24—C23—H23	120.6
C12—C4—C5	116.3 (3)	C23—C24—C25	123.5 (4)
C6—C5—N3	110.5 (3)	C23—C24—N6	116.4 (4)
C6—C5—C4	121.0 (3)	C25—C24—N6	120.0 (3)
N3—C5—C4	128.5 (4)	O3—C25—C24	121.1 (3)
C5—C6—N4	105.3 (3)	O3—C25—C20	124.0 (3)
C5—C6—C7	124.8 (3)	C24—C25—C20	114.9 (3)
N4—C6—C7	129.9 (4)	O2—C26—O1	122.3 (4)
C8—C7—C11	117.7 (3)	O2—C26—C20	119.4 (3)
C8—C7—C6	127.5 (4)	O1—C26—C20	118.2 (3)
C11—C7—C6	114.8 (3)	C1—N1—C12	118.8 (3)
C9—C8—C7	119.6 (4)	C1—N1—Co	127.4 (2)
C9—C8—H8	120.2	C12—N1—Co	113.2 (2)
C7—C8—H8	120.2	C10—N2—C11	119.2 (3)
C8—C9—C10	119.4 (4)	C10—N2—Co	127.0 (2)
C8—C9—H9	120.3	C11—N2—Co	113.5 (2)
C10—C9—H9	120.3	C13—N3—C5	104.8 (3)
N2—C10—C9	122.7 (4)	C13—N4—C6	107.2 (3)
N2—C10—H10	118.7	C13—N4—H4	126.4
C9—C10—H10	118.7	C6—N4—H4	126.4
N2—C11—C7	121.5 (3)	O4—N5—O5	123.0 (4)
N2—C11—C12	116.9 (3)	O4—N5—C22	119.2 (4)
C7—C11—C12	121.7 (3)	O5—N5—C22	117.9 (4)
N1—C12—C4	122.0 (3)	O7—N6—O6	119.1 (4)
N1—C12—C11	116.5 (3)	O7—N6—C24	121.8 (4)
C4—C12—C11	121.5 (3)	O6—N6—C24	118.9 (3)
N3—C13—N4	112.1 (3)	C26—O1—Co	120.4 (3)
N3—C13—C14	125.6 (4)	C26—O1—Co^i	125.8 (2)
N4—C13—C14	122.2 (4)	Co—O1—Co^i	100.87 (10)
C19—C14—C15	119.4 (4)	C25—O3—Co	127.0 (2)
C19—C14—C13	120.8 (4)	Co—OW1—H1WA	116 (4)
C15—C14—C13	119.8 (4)	Co—OW1—H1WB	124 (4)
C14—C15—C16	119.4 (5)	H1WA—OW1—H1WB	102 (5)
C14—C15—H15	120.3	O3—Co—O1	87.05 (10)
C16—C15—H15	120.3	O3—Co—N2	175.08 (14)
C17—C16—C15	120.9 (5)	O1—Co—N2	96.09 (11)
C17—C16—H16	119.5	O3—Co—N1	98.70 (11)
C15—C16—H16	119.5	O1—Co—N1	167.77 (12)
C16—C17—C18	119.7 (4)	N2—Co—N1	78.95 (12)
C16—C17—H17	120.1	O3—Co—OW1	88.76 (12)
C18—C17—H17	120.1	O1—Co—OW1	95.00 (13)
C17—C18—C19	120.5 (5)	N2—Co—OW1	87.20 (12)
C17—C18—H18	119.7	N1—Co—OW1	95.91 (13)
C19—C18—H18	119.7	O3—Co—O1^i	95.02 (11)
C18—C19—C14	120.0 (5)	O1—Co—O1^i	79.13 (10)
C18—C19—H19	120.0	N2—Co—O1^i	89.30 (11)
C14—C19—H19	120.0	N1—Co—O1^i	89.56 (11)
C21—C20—C25	119.9 (4)	OW1—Co—O1^i	172.82 (12)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O6^ii	0.86	2.17	2.948 (5)	150
OW1—H1WA···N3^iii	0.81 (6)	2.03 (6)	2.831 (5)	172 (5)
OW1—H1WB···O2^iv	0.80 (5)	1.88 (5)	2.662 (4)	165 (5)

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