catena-Poly[[aqua­(dipyrido[3,2-a:2′,3′-c]phenazine)cobalt(II)]-μ-benzene-1,4-dicarboxyl­ato]

Fang-Wei; Mei, Z.-M.

doi:10.1107/S1600536807056826

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catena-Poly[[aqua(dipyrido[3,2-a:2′,3′-c]phenazine)cobalt(II)]-μ-benzene-1,4-dicarboxylato]

Fang-Wei and Z.-M. Mei

In the title compound, [Co(C₈H₄O₄)(C₁₈H₁₀N₄)(H₂O)]_n, the Co^II atom is six-coordinated by three O atoms from two benzene-1,4-dicarboxylate (1,4-BDC) dianions (one bidentate and one monodentate), one water molecule and two N atoms from a bidentate dipyrido[3,2-a:2′,3′-c]phenazine ligand, resulting in a distorted cis-CoO₄N₂ octahedral geometry. The Co^II atoms are bridged by the 1,4-BDC ligands, forming a single-chain polymer structure. Both BDC ligands are centrosymmetric. Neighbouring chains interact through π–π interactions [minimum centroid–centroid separation = 3.459 (2) Å] and O—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056826/hb2627sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056826/hb2627Isup2.hkl Contains datablock I

CCDC reference: 672718

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.006 Å
R factor = 0.047
wR factor = 0.114
Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density ....       4.21

Alert level C
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...          4
PLAT333_ALERT_2_C Large Average Benzene C-C Dist.  C4     -C18           1.43 Ang.
PLAT350_ALERT_3_C Short   C-H Bond (0.96A)   C30    -   H30    ...       0.84 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Co1         (9)       1.65

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

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

Comment top

1,10-Phenanthroline (phen) and its derivatives are important ligands with numerous uses in the constructon of metal-organic complexes. Supramolecular architectures based on the dipydo[3,2 - a:2',3'-c]phenazine (Dppz) molecule have considerably less attention (Li et al., 2006) As part of our ongoing studies in this area (Li et al., 2007), we now report the sythesis and structure of the title compound,(I), containing Co_II ions, 1,4-BDC anions and phe-derived dipydo[3,2 - a:2',3'-c]phenazine (C₁₈H₁₀N₄) ligands.

In compound (I), the Co^II atom is six-coordinated by two N atoms from one Dppz molecule, three O atoms from two 1,4-BDC dianions (one monodentate, one bidentate) and one water molecule (Fig. 1, Table 1): a distorted octahedral cis-CoN₂O₄ arrangement is formed.

Neighboring Co^II atoms are bridged by the centrosymmetric 1,4-BDC ligands forming a one-dimensional chain structure (Fig. 2). In the crystal structure, adjacent chains are connected through π-π interactions between dppz and 1,4-BDC ligands with a minimum centroid-centroid stacking distance of 3.459 (2) Å. O—H···O hydrogen bonds involving the water molecules and carboxylate O atom acceptors (Table 2) complete the structure of (I).

Related literature top

For related structures, see Li et al. (2006, 2007). For the ligand synthesis, see Dickeson & Summers (1970).

Experimental top

The Dppz ligand was synthesized by the literature method of Dickeson & Summers (1970). A mixture of CoCl₂.2H₂O (0.3 mmol), Dppz (0.1 mmol) and benzene-1,4-dicarboxylic acid (0.3 mmol) in 30 ml of distilled water was stirred thoroughly for 1 h at ambient temperature. The pH value was adjusted to about 7.5 with NaOH aqueous solution. The suspension was sealed in a Teflon-lined stainless reaction vessel (40 ml) and heated at 443 K for 5 days. The vessel was cooled slowly to room temperature at a rate of 10 K h^-1 before opening, and purple blocks of (I) were recovered.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXTL-Plus.

Figures top

	Fig. 1. The asymmetric unit of (I), together with additional atoms to complete the coordination of Co1 with displacement ellipsoids drawn at the 30% probability level (arbitrary spheres for the H atoms). [Symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) -x, -y, 1 - z.
	Fig. 2. A view of the polymeric chain structure of (I). H atoms have been omitted for clarity.

catena-Poly[[aqua(dipyrido[3,2 - a:2',3'-c]phenazine)cobalt(II)]-µ-benzene- 1,4-dicarboxylato] top

Crystal data top

[Co(C₈H₄O₄)(C₁₈H₁₀N₄)(H₂O)]	F(000) = 1068.0
M_r = 523.36	D_x = 1.587 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1368 reflections
a = 10.5218 (19) Å	θ = 2.3–26.1°
b = 11.742 (2) Å	µ = 0.83 mm⁻¹
c = 18.077 (3) Å	T = 292 K
β = 101.281 (4)°	Block, purple
V = 2190.2 (7) Å³	0.47 × 0.21 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	4317 independent reflections
Radiation source: fine-focus sealed tube	2417 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
Detector resolution: 0 pixels mm^-1	θ_max = 26.0°, θ_min = 2.1°
ω scans	h = −12→10
Absorption correction: multi-scan (SADABS; Bruker, 2002)	k = −14→11
T_min = 0.815, T_max = 0.924	l = −20→22
11590 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 0.88	w = 1/[σ²(F_o²) + (0.0475P)²] where P = (F_o² + 2F_c²)/3
4317 reflections	(Δ/σ)_max = 0.001
349 parameters	Δρ_max = 1.70 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

[Co(C₈H₄O₄)(C₁₈H₁₀N₄)(H₂O)]	V = 2190.2 (7) Å³
M_r = 523.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.5218 (19) Å	µ = 0.83 mm⁻¹
b = 11.742 (2) Å	T = 292 K
c = 18.077 (3) Å	0.47 × 0.21 × 0.10 mm
β = 101.281 (4)°

Data collection top

Bruker APEXII diffractometer	4317 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2417 reflections with I > 2σ(I)
T_min = 0.815, T_max = 0.924	R_int = 0.059
11590 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 0.88	Δρ_max = 1.70 e Å⁻³
4317 reflections	Δρ_min = −0.40 e Å⁻³
349 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	0.49412 (5)	0.06855 (4)	0.63798 (3)	0.03467 (18)
O1	0.3496 (3)	−0.0366 (2)	0.57392 (15)	0.0440 (7)
O2	0.2835 (3)	0.1061 (2)	0.63506 (15)	0.0487 (8)
O3	0.6371 (3)	0.0100 (3)	0.58260 (19)	0.0450 (8)
N1	0.5516 (3)	−0.0670 (3)	0.72031 (16)	0.0367 (8)
C5	0.6497 (3)	−0.0620 (3)	0.9301 (2)	0.0363 (9)
N3	0.6541 (3)	0.1013 (3)	1.01155 (18)	0.0431 (9)
N4	0.6879 (3)	−0.1346 (3)	0.98703 (19)	0.0451 (9)
N2	0.5349 (3)	0.1544 (3)	0.74323 (17)	0.0380 (8)
C6	0.7111 (4)	−0.0898 (4)	1.0577 (2)	0.0437 (11)
C4	0.6252 (4)	−0.1065 (3)	0.8530 (2)	0.0367 (10)
C18	0.5825 (3)	−0.0328 (3)	0.7924 (2)	0.0326 (9)
C12	0.6338 (3)	0.0564 (3)	0.9431 (2)	0.0368 (9)
C10	0.7204 (4)	0.0719 (4)	1.1443 (2)	0.0578 (13)
H10A	0.7108	0.1493	1.1527	0.069*
C13	0.5971 (4)	0.1338 (3)	0.8784 (2)	0.0373 (10)
C17	0.5705 (3)	0.0889 (3)	0.8059 (2)	0.0337 (9)
C19	0.2598 (4)	0.0287 (4)	0.5870 (2)	0.0401 (10)
C11	0.6939 (4)	0.0280 (4)	1.0695 (2)	0.0447 (11)
C1	0.5651 (4)	−0.1773 (3)	0.7058 (2)	0.0471 (11)
H1B	0.5425	−0.2025	0.6562	0.057*
C3	0.6421 (4)	−0.2206 (4)	0.8354 (2)	0.0489 (11)
H3B	0.6739	−0.2724	0.8734	0.059*
C14	0.5886 (4)	0.2511 (4)	0.8866 (2)	0.0520 (12)
H14A	0.6084	0.2842	0.9342	0.062*
C8	0.7748 (4)	−0.1170 (5)	1.1915 (3)	0.0652 (15)
H8A	0.8001	−0.1649	1.2327	0.078*
C2	0.6120 (4)	−0.2560 (4)	0.7623 (2)	0.0564 (13)
H2B	0.6225	−0.3319	0.7502	0.068*
C16	0.5236 (4)	0.2654 (3)	0.7536 (2)	0.0490 (12)
H16A	0.4958	0.3109	0.7115	0.059*
C9	0.7600 (4)	0.0000 (5)	1.2033 (3)	0.0633 (14)
H9A	0.7773	0.0288	1.2522	0.076*
C7	0.7525 (4)	−0.1619 (4)	1.1197 (2)	0.0551 (12)
H7A	0.7647	−0.2392	1.1124	0.066*
C15	0.5509 (5)	0.3175 (4)	0.8239 (2)	0.0578 (13)
H15A	0.5436	0.3960	0.8283	0.069*
O4	0.5077 (3)	0.2196 (2)	0.58662 (15)	0.0508 (8)
O5	0.3983 (3)	0.2030 (2)	0.46817 (16)	0.0588 (9)
C27	0.4606 (4)	0.2578 (3)	0.5222 (2)	0.0405 (10)
C30	0.5377 (4)	0.4530 (3)	0.5701 (2)	0.0384 (10)
C29	0.4429 (4)	0.4323 (4)	0.4403 (2)	0.0388 (10)
C28	0.4816 (4)	0.3832 (3)	0.5108 (2)	0.0344 (9)
C21	0.0943 (4)	−0.0796 (4)	0.4949 (2)	0.0406 (10)
C20	0.1242 (4)	0.0122 (3)	0.5429 (2)	0.0342 (9)
C22	0.0299 (4)	0.0927 (4)	0.5484 (2)	0.0408 (11)
H30	0.565 (3)	0.424 (3)	0.613 (2)	0.040 (12)*
H22	0.049 (3)	0.156 (3)	0.5768 (19)	0.036 (11)*
H21	0.161 (3)	−0.133 (3)	0.4907 (18)	0.033 (10)*
H3WA	0.631 (4)	0.045 (4)	0.534 (3)	0.075 (16)*
H3WB	0.628 (5)	−0.048 (4)	0.568 (3)	0.08 (2)*
H29	0.404 (4)	0.391 (3)	0.401 (2)	0.051 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0429 (3)	0.0306 (3)	0.0290 (3)	−0.0023 (3)	0.0033 (2)	0.0023 (3)
O1	0.0375 (17)	0.0438 (17)	0.0486 (18)	0.0018 (14)	0.0032 (14)	0.0048 (14)
O2	0.0464 (19)	0.059 (2)	0.0369 (17)	−0.0066 (15)	−0.0003 (14)	−0.0121 (15)
O3	0.056 (2)	0.037 (2)	0.045 (2)	−0.0058 (16)	0.0153 (16)	−0.0020 (17)
N1	0.049 (2)	0.0328 (18)	0.0278 (18)	−0.0049 (17)	0.0053 (15)	−0.0004 (16)
C5	0.032 (2)	0.047 (2)	0.029 (2)	−0.003 (2)	0.0049 (17)	0.009 (2)
N3	0.041 (2)	0.059 (2)	0.030 (2)	−0.0001 (17)	0.0070 (16)	0.0010 (17)
N4	0.042 (2)	0.057 (2)	0.035 (2)	−0.0023 (17)	0.0052 (17)	0.0077 (18)
N2	0.042 (2)	0.036 (2)	0.034 (2)	0.0000 (16)	0.0029 (16)	0.0030 (16)
C6	0.037 (2)	0.063 (3)	0.031 (2)	−0.004 (2)	0.0061 (19)	0.010 (2)
C4	0.036 (2)	0.037 (2)	0.038 (2)	−0.0012 (18)	0.0081 (19)	0.0047 (19)
C18	0.033 (2)	0.031 (2)	0.033 (2)	−0.0046 (17)	0.0043 (18)	0.0020 (17)
C12	0.034 (2)	0.049 (3)	0.027 (2)	−0.002 (2)	0.0035 (17)	0.004 (2)
C10	0.054 (3)	0.084 (4)	0.035 (3)	−0.002 (3)	0.009 (2)	−0.001 (3)
C13	0.038 (3)	0.043 (3)	0.030 (2)	−0.0001 (19)	0.0029 (19)	0.0008 (18)
C17	0.032 (2)	0.039 (2)	0.029 (2)	−0.0021 (18)	0.0024 (17)	0.0018 (18)
C19	0.044 (3)	0.046 (3)	0.030 (2)	−0.008 (2)	0.007 (2)	0.013 (2)
C11	0.033 (2)	0.070 (3)	0.030 (2)	−0.002 (2)	0.0035 (19)	0.002 (2)
C1	0.071 (3)	0.035 (3)	0.034 (2)	0.000 (2)	0.009 (2)	−0.003 (2)
C3	0.063 (3)	0.039 (3)	0.043 (3)	0.003 (2)	0.008 (2)	0.013 (2)
C14	0.066 (3)	0.048 (3)	0.039 (3)	0.001 (2)	0.003 (2)	−0.008 (2)
C8	0.060 (3)	0.093 (4)	0.038 (3)	−0.006 (3)	0.000 (2)	0.021 (3)
C2	0.096 (4)	0.031 (2)	0.040 (3)	0.001 (2)	0.007 (3)	0.004 (2)
C16	0.068 (3)	0.036 (3)	0.041 (3)	0.003 (2)	0.006 (2)	0.005 (2)
C9	0.061 (3)	0.092 (4)	0.034 (3)	−0.011 (3)	0.006 (2)	0.001 (3)
C7	0.053 (3)	0.069 (3)	0.040 (3)	−0.005 (2)	0.001 (2)	0.012 (2)
C15	0.090 (4)	0.032 (3)	0.049 (3)	0.006 (2)	0.006 (3)	−0.004 (2)
O4	0.075 (2)	0.0348 (16)	0.0403 (17)	−0.0023 (15)	0.0061 (15)	0.0125 (14)
O5	0.096 (2)	0.0325 (17)	0.0463 (19)	−0.0056 (17)	0.0109 (18)	−0.0029 (15)
C27	0.050 (3)	0.035 (2)	0.041 (3)	0.002 (2)	0.019 (2)	0.004 (2)
C30	0.044 (3)	0.036 (3)	0.034 (2)	0.003 (2)	0.007 (2)	0.012 (2)
C29	0.047 (3)	0.035 (2)	0.035 (2)	−0.005 (2)	0.007 (2)	0.000 (2)
C28	0.037 (2)	0.030 (2)	0.037 (2)	0.0043 (18)	0.0109 (19)	0.0021 (18)
C21	0.039 (3)	0.040 (3)	0.043 (2)	0.004 (2)	0.008 (2)	−0.003 (2)
C20	0.037 (2)	0.037 (2)	0.028 (2)	−0.0051 (19)	0.0049 (18)	0.0017 (18)
C22	0.044 (3)	0.040 (3)	0.038 (3)	−0.006 (2)	0.006 (2)	−0.008 (2)

Geometric parameters (Å, º) top

Co1—O4	2.020 (3)	C19—C20	1.505 (5)
Co1—O3	2.080 (3)	C1—C2	1.394 (5)
Co1—O1	2.119 (3)	C1—H1B	0.9300
Co1—N2	2.122 (3)	C3—C2	1.362 (5)
Co1—N1	2.182 (3)	C3—H3B	0.9300
Co1—O2	2.250 (3)	C14—C15	1.369 (5)
Co1—C19	2.501 (4)	C14—H14A	0.9300
O1—C19	1.275 (5)	C8—C7	1.377 (6)
O2—C19	1.248 (5)	C8—C9	1.404 (7)
O3—H3WA	0.96 (5)	C8—H8A	0.9300
O3—H3WB	0.73 (5)	C2—H2B	0.9300
N1—C1	1.335 (4)	C16—C15	1.389 (5)
N1—C18	1.340 (4)	C16—H16A	0.9300
C5—N4	1.336 (4)	C9—H9A	0.9300
C5—C12	1.426 (5)	C7—H7A	0.9300
C5—C4	1.462 (5)	C15—H15A	0.9300
N3—C12	1.323 (5)	O4—C27	1.257 (4)
N3—C11	1.358 (5)	O5—C27	1.243 (4)
N4—C6	1.358 (5)	C27—C28	1.509 (5)
N2—C16	1.325 (5)	C30—C29ⁱ	1.381 (5)
N2—C17	1.360 (4)	C30—C28	1.386 (5)
C6—C7	1.404 (5)	C30—H30	0.85 (3)
C6—C11	1.416 (6)	C29—C30ⁱ	1.381 (5)
C4—C3	1.397 (5)	C29—C28	1.386 (5)
C4—C18	1.401 (5)	C29—H29	0.89 (4)
C18—C17	1.460 (5)	C21—C20	1.380 (5)
C12—C13	1.471 (5)	C21—C22ⁱⁱ	1.394 (5)
C10—C9	1.360 (6)	C21—H21	0.96 (3)
C10—C11	1.422 (5)	C20—C22	1.389 (5)
C10—H10A	0.9300	C22—C21ⁱⁱ	1.394 (5)
C13—C17	1.389 (5)	C22—H22	0.91 (3)
C13—C14	1.390 (5)

O4—Co1—O3	86.90 (14)	O2—C19—O1	120.9 (4)
O4—Co1—O1	111.62 (10)	O2—C19—C20	120.2 (4)
O3—Co1—O1	93.07 (12)	O1—C19—C20	118.9 (4)
O4—Co1—N2	88.55 (12)	O2—C19—Co1	63.9 (2)
O3—Co1—N2	123.37 (12)	O1—C19—Co1	57.9 (2)
O1—Co1—N2	139.90 (12)	C20—C19—Co1	169.5 (3)
O4—Co1—N1	156.75 (11)	N3—C11—C6	122.1 (4)
O3—Co1—N1	87.56 (13)	N3—C11—C10	118.5 (4)
O1—Co1—N1	91.21 (11)	C6—C11—C10	119.4 (4)
N2—Co1—N1	75.79 (12)	N1—C1—C2	122.4 (4)
O4—Co1—O2	88.58 (11)	N1—C1—H1B	118.8
O3—Co1—O2	148.78 (12)	C2—C1—H1B	118.8
O1—Co1—O2	60.22 (10)	C2—C3—C4	119.9 (4)
N2—Co1—O2	87.34 (11)	C2—C3—H3B	120.1
N1—Co1—O2	107.40 (11)	C4—C3—H3B	120.1
O4—Co1—C19	98.53 (12)	C15—C14—C13	119.4 (4)
O3—Co1—C19	120.97 (14)	C15—C14—H14A	120.3
O1—Co1—C19	30.64 (11)	C13—C14—H14A	120.3
N2—Co1—C19	115.53 (14)	C7—C8—C9	121.0 (5)
N1—Co1—C19	103.67 (12)	C7—C8—H8A	119.5
O2—Co1—C19	29.85 (11)	C9—C8—H8A	119.5
C19—O1—Co1	91.5 (2)	C3—C2—C1	119.4 (4)
C19—O2—Co1	86.3 (2)	C3—C2—H2B	120.3
Co1—O3—H3WA	112 (3)	C1—C2—H2B	120.3
Co1—O3—H3WB	115 (4)	N2—C16—C15	123.7 (4)
H3WA—O3—H3WB	95 (5)	N2—C16—H16A	118.1
C1—N1—C18	117.8 (3)	C15—C16—H16A	118.1
C1—N1—Co1	126.9 (3)	C10—C9—C8	120.9 (5)
C18—N1—Co1	115.2 (2)	C10—C9—H9A	119.6
N4—C5—C12	121.4 (4)	C8—C9—H9A	119.6
N4—C5—C4	118.5 (4)	C8—C7—C6	119.4 (5)
C12—C5—C4	120.1 (3)	C8—C7—H7A	120.3
C12—N3—C11	116.0 (4)	C6—C7—H7A	120.3
C5—N4—C6	116.7 (4)	C14—C15—C16	118.7 (4)
C16—N2—C17	117.1 (3)	C14—C15—H15A	120.6
C16—N2—Co1	125.9 (3)	C16—C15—H15A	120.6
C17—N2—Co1	116.9 (2)	C27—O4—Co1	133.5 (3)
N4—C6—C7	119.2 (4)	O5—C27—O4	126.5 (4)
N4—C6—C11	121.0 (4)	O5—C27—C28	117.9 (4)
C7—C6—C11	119.8 (4)	O4—C27—C28	115.6 (4)
C3—C4—C18	116.7 (4)	C29ⁱ—C30—C28	121.5 (4)
C3—C4—C5	123.6 (4)	C29ⁱ—C30—H30	119 (3)
C18—C4—C5	119.6 (4)	C28—C30—H30	120 (3)
N1—C18—C4	123.7 (3)	C30ⁱ—C29—C28	120.4 (4)
N1—C18—C17	116.4 (3)	C30ⁱ—C29—H29	118 (3)
C4—C18—C17	119.9 (3)	C28—C29—H29	121 (3)
N3—C12—C5	122.7 (3)	C30—C28—C29	118.0 (4)
N3—C12—C13	117.8 (4)	C30—C28—C27	121.6 (4)
C5—C12—C13	119.5 (3)	C29—C28—C27	120.4 (4)
C9—C10—C11	119.6 (5)	C20—C21—C22ⁱⁱ	120.8 (4)
C9—C10—H10A	120.2	C20—C21—H21	119 (2)
C11—C10—H10A	120.2	C22ⁱⁱ—C21—H21	120 (2)
C17—C13—C14	118.1 (4)	C21—C20—C22	119.9 (4)
C17—C13—C12	119.2 (3)	C21—C20—C19	120.7 (4)
C14—C13—C12	122.7 (4)	C22—C20—C19	119.4 (4)
N2—C17—C13	122.9 (3)	C20—C22—C21ⁱⁱ	119.3 (4)
N2—C17—C18	115.6 (3)	C20—C22—H22	122 (2)
C13—C17—C18	121.5 (3)	C21ⁱⁱ—C22—H22	119 (2)

O4—Co1—O1—C19	−69.1 (2)	Co1—O2—C19—O1	10.2 (4)
O3—Co1—O1—C19	−157.0 (2)	Co1—O2—C19—C20	−169.0 (3)
N2—Co1—O1—C19	46.2 (3)	Co1—O1—C19—O2	−10.9 (4)
N1—Co1—O1—C19	115.4 (2)	Co1—O1—C19—C20	168.4 (3)
O2—Co1—O1—C19	5.9 (2)	O4—Co1—C19—O2	−71.8 (2)
O4—Co1—O2—C19	110.0 (2)	O3—Co1—C19—O2	−163.3 (2)
O3—Co1—O2—C19	28.3 (4)	O1—Co1—C19—O2	169.6 (4)
O1—Co1—O2—C19	−6.1 (2)	N2—Co1—C19—O2	20.6 (3)
N2—Co1—O2—C19	−161.4 (2)	N1—Co1—C19—O2	101.2 (2)
N1—Co1—O2—C19	−87.2 (2)	O4—Co1—C19—O1	118.6 (2)
O4—Co1—N1—C1	−127.2 (4)	O3—Co1—C19—O1	27.0 (3)
O3—Co1—N1—C1	−50.9 (3)	N2—Co1—C19—O1	−149.0 (2)
O1—Co1—N1—C1	42.2 (3)	N1—Co1—C19—O1	−68.4 (2)
N2—Co1—N1—C1	−176.2 (3)	O2—Co1—C19—O1	−169.6 (4)
O2—Co1—N1—C1	101.2 (3)	O4—Co1—C19—C20	43.3 (18)
C19—Co1—N1—C1	70.5 (4)	O3—Co1—C19—C20	−48.2 (18)
O4—Co1—N1—C18	49.1 (5)	O1—Co1—C19—C20	−75.2 (17)
O3—Co1—N1—C18	125.4 (3)	N2—Co1—C19—C20	135.8 (17)
O1—Co1—N1—C18	−141.6 (3)	N1—Co1—C19—C20	−143.6 (17)
N2—Co1—N1—C18	0.1 (3)	O2—Co1—C19—C20	115.2 (18)
O2—Co1—N1—C18	−82.5 (3)	C12—N3—C11—C6	−0.8 (6)
C19—Co1—N1—C18	−113.3 (3)	C12—N3—C11—C10	178.4 (4)
C12—C5—N4—C6	−0.2 (5)	N4—C6—C11—N3	−0.1 (6)
C4—C5—N4—C6	179.3 (3)	C7—C6—C11—N3	180.0 (4)
O4—Co1—N2—C16	18.7 (3)	N4—C6—C11—C10	−179.4 (4)
O3—Co1—N2—C16	104.0 (4)	C7—C6—C11—C10	0.7 (6)
O1—Co1—N2—C16	−104.1 (4)	C9—C10—C11—N3	179.7 (4)
N1—Co1—N2—C16	−178.6 (4)	C9—C10—C11—C6	−1.0 (6)
O2—Co1—N2—C16	−69.9 (3)	C18—N1—C1—C2	−1.2 (6)
C19—Co1—N2—C16	−80.0 (4)	Co1—N1—C1—C2	175.0 (3)
O4—Co1—N2—C17	−164.4 (3)	C18—C4—C3—C2	−2.8 (6)
O3—Co1—N2—C17	−79.0 (3)	C5—C4—C3—C2	177.3 (4)
O1—Co1—N2—C17	72.8 (3)	C17—C13—C14—C15	2.0 (6)
N1—Co1—N2—C17	−1.7 (3)	C12—C13—C14—C15	−178.5 (4)
O2—Co1—N2—C17	107.0 (3)	C4—C3—C2—C1	0.4 (7)
C19—Co1—N2—C17	96.9 (3)	N1—C1—C2—C3	1.8 (7)
C5—N4—C6—C7	−179.5 (4)	C17—N2—C16—C15	2.7 (6)
C5—N4—C6—C11	0.7 (6)	Co1—N2—C16—C15	179.6 (3)
N4—C5—C4—C3	−1.4 (6)	C11—C10—C9—C8	0.0 (7)
C12—C5—C4—C3	178.1 (4)	C7—C8—C9—C10	1.4 (7)
N4—C5—C4—C18	178.6 (3)	C9—C8—C7—C6	−1.6 (7)
C12—C5—C4—C18	−1.9 (6)	N4—C6—C7—C8	−179.3 (4)
C1—N1—C18—C4	−1.5 (6)	C11—C6—C7—C8	0.5 (6)
Co1—N1—C18—C4	−178.1 (3)	C13—C14—C15—C16	−0.8 (7)
C1—N1—C18—C17	178.1 (3)	N2—C16—C15—C14	−1.7 (7)
Co1—N1—C18—C17	1.5 (4)	O3—Co1—O4—C27	82.1 (4)
C3—C4—C18—N1	3.4 (6)	O1—Co1—O4—C27	−10.0 (4)
C5—C4—C18—N1	−176.6 (3)	N2—Co1—O4—C27	−154.4 (4)
C3—C4—C18—C17	−176.1 (4)	N1—Co1—O4—C27	158.6 (4)
C5—C4—C18—C17	3.9 (5)	O2—Co1—O4—C27	−67.0 (4)
C11—N3—C12—C5	1.3 (6)	C19—Co1—O4—C27	−38.8 (4)
C11—N3—C12—C13	−176.9 (3)	Co1—O4—C27—O5	−7.5 (7)
N4—C5—C12—N3	−0.8 (6)	Co1—O4—C27—C28	171.8 (3)
C4—C5—C12—N3	179.7 (3)	C29ⁱ—C30—C28—C29	−1.2 (7)
N4—C5—C12—C13	177.4 (3)	C29ⁱ—C30—C28—C27	179.9 (4)
C4—C5—C12—C13	−2.1 (5)	C30ⁱ—C29—C28—C30	1.2 (7)
N3—C12—C13—C17	−177.7 (4)	C30ⁱ—C29—C28—C27	−179.9 (4)
C5—C12—C13—C17	4.1 (5)	O5—C27—C28—C30	173.0 (4)
N3—C12—C13—C14	2.8 (6)	O4—C27—C28—C30	−6.3 (6)
C5—C12—C13—C14	−175.4 (4)	O5—C27—C28—C29	−5.9 (6)
C16—N2—C17—C13	−1.3 (6)	O4—C27—C28—C29	174.8 (4)
Co1—N2—C17—C13	−178.5 (3)	C22ⁱⁱ—C21—C20—C22	0.0 (7)
C16—N2—C17—C18	−179.8 (3)	C22ⁱⁱ—C21—C20—C19	−177.4 (4)
Co1—N2—C17—C18	3.0 (4)	O2—C19—C20—C21	−173.8 (4)
C14—C13—C17—N2	−1.0 (6)	O1—C19—C20—C21	7.0 (5)
C12—C13—C17—N2	179.5 (3)	Co1—C19—C20—C21	76.3 (18)
C14—C13—C17—C18	177.4 (4)	O2—C19—C20—C22	8.8 (6)
C12—C13—C17—C18	−2.2 (6)	O1—C19—C20—C22	−170.5 (4)
N1—C18—C17—N2	−2.9 (5)	Co1—C19—C20—C22	−101.2 (18)
C4—C18—C17—N2	176.6 (3)	C21—C20—C22—C21ⁱⁱ	0.0 (7)
N1—C18—C17—C13	178.6 (4)	C19—C20—C22—C21ⁱⁱ	177.4 (4)
C4—C18—C17—C13	−1.9 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3WA···O1ⁱⁱⁱ	0.96 (5)	2.00 (5)	2.877 (4)	151 (4)
O3—H3WB···O5ⁱⁱⁱ	0.73 (5)	1.94 (5)	2.666 (4)	179 (6)

Symmetry code: (iii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Co(C₈H₄O₄)(C₁₈H₁₀N₄)(H₂O)]
M_r	523.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	292
a, b, c (Å)	10.5218 (19), 11.742 (2), 18.077 (3)
β (°)	101.281 (4)
V (Å³)	2190.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.83
Crystal size (mm)	0.47 × 0.21 × 0.10

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.815, 0.924
No. of measured, independent and observed [I > 2σ(I)] reflections	11590, 4317, 2417
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.114, 0.88
No. of reflections	4317
No. of parameters	349
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.70, −0.40

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990), SHELXTL-Plus.

Selected geometric parameters (Å, º) top

Co1—O4	2.020 (3)	Co1—N2	2.122 (3)
Co1—O3	2.080 (3)	Co1—N1	2.182 (3)
Co1—O1	2.119 (3)	Co1—O2	2.250 (3)

N2—Co1—N1	75.79 (12)	O1—Co1—O2	60.22 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3WA···O1ⁱ	0.96 (5)	2.00 (5)	2.877 (4)	151 (4)
O3—H3WB···O5ⁱ	0.73 (5)	1.94 (5)	2.666 (4)	179 (6)

Symmetry code: (i) −x+1, −y, −z+1.

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