catena-Poly[[diaqua­(1,10-phenanthroline-κ2N,N′)cobalt(II)]-μ-trans-stilbene-4,4′-dicarboxyl­ato-κ2O:O′]

Wang, H.-Y.; Gao, S.; Huo, L.-H.; Zhao, J.-G.

doi:10.1107/S1600536807057959

catena-Poly[[diaqua(1,10-phenanthroline-κ²N,N′)cobalt(II)]-μ-trans-stilbene-4,4′-dicarboxylato-κ²O:O′]

H.-Y. Wang, S. Gao, L.-H. Huo and J.-G. Zhao

In the title complex, [Co(C₁₆H₁₀O₄)(C₁₂H₈N₂)(H₂O)₂]_n, the Co^II ion exists in an octahedral geometry, coordinated by two N atoms of a 1,10-phenanthroline ligand, two carboxylate O atoms of two different trans-stilbene-4,4′-dicarboxylate ligands and two water molecules. The trans-stilbene-4,4′-dicarboxylate bridges give rise to a linear chain structure. These chains are further interconnected through intermolecular hydrogen bonds and π–π stacking interactions between one of the rings of the 1,10-phenanthroline ligand and a symmetry-related ring [centroid-to-centroid distance 3.6153 (8) Å], to form a three-dimensional supramolecular network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807057959/ng2367sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807057959/ng2367Isup2.hkl Contains datablock I

CCDC reference: 672680

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Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.005 Å
R factor = 0.043
wR factor = 0.142
Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of .     105.00 A   3 

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Co1         (9)       1.28
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          6

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

   1 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
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Many new complexes have been synthesized using polycarboxylates to combine with specific transition metal ions by introdcing neutral N-heterocyclic ligands (Wang et al., 2004; Wang, Qin et al., 2006). We report here the synthesis and structure of a new one-dimensional cobalt complex (Fig. 1).

The complex is an infinite one-dimensional chain polymer with a Co^II ion, two half of trans-stilbene-4,4'-dicarboxylato ligands, a 1,10-phenanthroline and two coordinated water molecules in the asymmetric unit. Each Co^II ion is in a distorted octahedral geometry. The [Co(1,10-phenanthroline)(H₂O)₂] units are connected by trans-stilbene-4,4'-dicarboxylato bridges with bis-dentate mode to form an one-dimensional zigzag chain structure. The chains are further interconnected through intermolecular hydrogen bonds and π–π stacking interactions between one of the rings of the 1,10-phenanthroline ligand (C7–C10/N2/C11) and symmetry-related ring at (1 - x, 2 - y, 1 - z), with a centroid-to-centroid distance of 3.6153 (8) Å into three-dimensional supramolecular network (Table 2 and Fig. 2). The structure contains voids of about 105.00 A³ and there is no solvent molecules occupied.

Related literature top

For the 1,10-phenanthroline-coordinated nickel derivative of trans-stilbene-4,4'-dicarboxylic acid, see Wang, Gao et al. (2006). For other zinc and cadmium complexes, see Wang et al. (2004); Wang, Qin et al. (2006). [Please note that the Related literature section must contain all those references, and only those references, that are cited in the Supplementary material. It cannot be used to cite references that are not cited elsewhere in the CIF. Thus, Wang, Gao et al. (2006) will be removed, unless you wish to provide a revised Comment or other section which cites it.]

Experimental top

A mixture of CoCl₂.6H₂O (1 mmol), 1,10-phenanthroline (1 mmol), trans-stilbene-4,4'-dicarboxylic acid(1 mmol) and water (10 ml) was stirred for 15 min in air, then transferred and sealed in a 23 ml Parr teflon-lined stainless steel vessel, heated to 160 ° for 5 days, and then cooled to room temperature. The resulting red crystals were filtered, washed, and dried in air. Analysis calculated for C₂₈H₂₂CoN₂O₆: C 62.12, H 4.10, N 5.17%; found: C 62.14, H 4.13, N 5.15%.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: publCIF (Westrip 2007).

Figures top

	Fig. 1. Molecular structure of the title compound. Dashed lines indicate O—H···O hydrogen bonds.
	Fig. 2. The packing diagram of the title complex, with the hydrogen bonds denoted by dashed lines.

catena-Poly[[diaqua(1,10-phenanthroline-κ²N,N')cobalt(II)]-µ-trans- stilbene-4,4'-dicarboxylato-κ²O:O'] top

Crystal data top

[Co(C₁₆H₁₀O₄)(C₁₂H₈N₂)H₂O)₂]	Z = 2
M_r = 541.41	F(000) = 558
Triclinic, P1	D_x = 1.446 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5345 (15) Å	Cell parameters from 10169 reflections
b = 9.2112 (18) Å	θ = 3.1–27.5°
c = 18.524 (4) Å	µ = 0.74 mm⁻¹
α = 88.12 (3)°	T = 295 K
β = 84.29 (3)°	Prism, pink
γ = 76.38 (3)°	0.36 × 0.24 × 0.12 mm
V = 1243.2 (5) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	5509 independent reflections
Radiation source: fine-focus sealed tube	4338 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 10 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −11→11
T_min = 0.811, T_max = 0.917	l = −23→24
11895 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0745P)² + 1.1034P] where P = (F_o² + 2F_c²)/3
5509 reflections	(Δ/σ)_max < 0.001
346 parameters	Δρ_max = 0.47 e Å⁻³
6 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

[Co(C₁₆H₁₀O₄)(C₁₂H₈N₂)H₂O)₂]	γ = 76.38 (3)°
M_r = 541.41	V = 1243.2 (5) Å³
Triclinic, P1	Z = 2
a = 7.5345 (15) Å	Mo Kα radiation
b = 9.2112 (18) Å	µ = 0.74 mm⁻¹
c = 18.524 (4) Å	T = 295 K
α = 88.12 (3)°	0.36 × 0.24 × 0.12 mm
β = 84.29 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	5509 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4338 reflections with I > 2σ(I)
T_min = 0.811, T_max = 0.917	R_int = 0.030
11895 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	6 restraints
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.47 e Å⁻³
5509 reflections	Δρ_min = −0.48 e Å⁻³
346 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	0.43923 (5)	0.65500 (4)	0.628861 (19)	0.02933 (13)
O1W	0.6521 (3)	0.5294 (3)	0.55787 (12)	0.0440 (5)
H1W1	0.675 (5)	0.513 (5)	0.5126 (7)	0.066*
H1W2	0.744 (3)	0.549 (5)	0.5747 (17)	0.066*
O2W	0.2624 (3)	0.5328 (2)	0.58733 (10)	0.0347 (4)
H2W1	0.1490 (17)	0.559 (3)	0.6021 (18)	0.052*
H2W2	0.310 (4)	0.451 (2)	0.6084 (18)	0.052*
O1	0.3931 (3)	0.3052 (2)	0.66551 (12)	0.0458 (5)
O2	0.4849 (3)	0.4951 (2)	0.71028 (11)	0.0428 (5)
O3	0.9059 (3)	0.5857 (3)	0.63524 (11)	0.0441 (5)
O4	0.6409 (3)	0.7378 (2)	0.67405 (11)	0.0347 (4)
N1	0.2421 (3)	0.8101 (3)	0.69611 (13)	0.0368 (5)
N2	0.3447 (3)	0.8322 (3)	0.55504 (13)	0.0339 (5)
C1	0.1957 (5)	0.7976 (4)	0.76617 (18)	0.0500 (8)
H1A	0.2489	0.7107	0.7904	0.060*
C2	0.0693 (6)	0.9103 (5)	0.8053 (2)	0.0656 (12)
H2A	0.0391	0.8979	0.8547	0.079*
C3	−0.0089 (6)	1.0383 (5)	0.7706 (3)	0.0683 (12)
H3A	−0.0946	1.1129	0.7961	0.082*
C4	0.0386 (5)	1.0581 (4)	0.6969 (2)	0.0524 (9)
C5	−0.0311 (5)	1.1907 (4)	0.6553 (3)	0.0650 (12)
H5A	−0.1155	1.2703	0.6779	0.078*
C6	0.0238 (5)	1.2009 (4)	0.5847 (3)	0.0612 (11)
H6A	−0.0231	1.2882	0.5594	0.073*
C7	0.1512 (4)	1.0830 (3)	0.5473 (2)	0.0452 (8)
C8	0.2095 (5)	1.0866 (4)	0.4735 (2)	0.0523 (9)
H8A	0.1656	1.1712	0.4459	0.063*
C9	0.3301 (5)	0.9673 (4)	0.44203 (19)	0.0486 (8)
H9A	0.3696	0.9696	0.3929	0.058*
C10	0.3943 (5)	0.8406 (4)	0.48433 (16)	0.0417 (7)
H10A	0.4752	0.7587	0.4620	0.050*
C11	0.2226 (4)	0.9508 (3)	0.58613 (17)	0.0354 (6)
C12	0.1659 (4)	0.9390 (3)	0.66163 (17)	0.0378 (7)
C13	0.7921 (4)	0.6514 (3)	0.68497 (15)	0.0314 (6)
C14	0.8366 (4)	0.6222 (3)	0.76200 (15)	0.0348 (6)
C15	0.7248 (5)	0.7048 (4)	0.81696 (18)	0.0522 (9)
H15A	0.6250	0.7798	0.8056	0.063*
C16	0.7589 (6)	0.6776 (5)	0.88847 (19)	0.0627 (11)
H16A	0.6814	0.7347	0.9245	0.075*
C17	0.9054 (5)	0.5675 (5)	0.90771 (18)	0.0539 (9)
C18	1.0162 (5)	0.4823 (4)	0.85223 (19)	0.0515 (9)
H18A	1.1141	0.4057	0.8638	0.062*
C19	0.9832 (4)	0.5096 (4)	0.78023 (17)	0.0416 (7)
H19A	1.0596	0.4522	0.7440	0.050*
C20	0.9339 (6)	0.5462 (5)	0.9859 (2)	0.0654 (11)
H20A	0.8468	0.6061	1.0181	0.079*
C21	0.4532 (4)	0.3663 (3)	0.71367 (15)	0.0344 (6)
C22	0.4856 (4)	0.2819 (3)	0.78413 (15)	0.0351 (6)
C23	0.5623 (5)	0.3377 (4)	0.83860 (17)	0.0432 (7)
H23A	0.6004	0.4265	0.8314	0.052*
C24	0.5825 (5)	0.2607 (4)	0.90439 (17)	0.0478 (8)
H24A	0.6365	0.2978	0.9405	0.057*
C25	0.5232 (5)	0.1291 (4)	0.91687 (16)	0.0442 (8)
C26	0.4475 (6)	0.0748 (4)	0.86118 (18)	0.0525 (9)
H26A	0.4070	−0.0129	0.8685	0.063*
C27	0.4311 (5)	0.1479 (4)	0.79540 (18)	0.0471 (8)
H27A	0.3834	0.1078	0.7583	0.057*
C28	0.5413 (5)	0.0533 (4)	0.98769 (17)	0.0498 (8)
H28A	0.6174	0.0827	1.0180	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0294 (2)	0.0318 (2)	0.02577 (19)	−0.00472 (15)	−0.00555 (13)	0.00541 (14)
O1W	0.0322 (11)	0.0621 (15)	0.0343 (11)	−0.0023 (11)	−0.0047 (9)	−0.0101 (10)
O2W	0.0312 (10)	0.0420 (12)	0.0305 (10)	−0.0074 (9)	−0.0042 (8)	0.0039 (8)
O1	0.0629 (15)	0.0392 (12)	0.0369 (11)	−0.0127 (11)	−0.0139 (10)	0.0058 (9)
O2	0.0573 (14)	0.0435 (12)	0.0338 (11)	−0.0216 (11)	−0.0153 (10)	0.0154 (9)
O3	0.0327 (11)	0.0638 (15)	0.0332 (11)	−0.0054 (11)	−0.0050 (9)	−0.0014 (10)
O4	0.0352 (11)	0.0336 (11)	0.0355 (10)	−0.0065 (9)	−0.0097 (8)	0.0035 (8)
N1	0.0325 (12)	0.0403 (14)	0.0376 (13)	−0.0092 (11)	−0.0017 (10)	−0.0001 (10)
N2	0.0339 (12)	0.0353 (13)	0.0339 (12)	−0.0093 (11)	−0.0086 (10)	0.0062 (10)
C1	0.051 (2)	0.060 (2)	0.0406 (17)	−0.0186 (18)	0.0056 (15)	−0.0054 (15)
C2	0.066 (3)	0.083 (3)	0.051 (2)	−0.031 (2)	0.0185 (19)	−0.021 (2)
C3	0.052 (2)	0.069 (3)	0.079 (3)	−0.008 (2)	0.017 (2)	−0.035 (2)
C4	0.0349 (17)	0.050 (2)	0.072 (2)	−0.0099 (16)	0.0013 (16)	−0.0196 (18)
C5	0.045 (2)	0.038 (2)	0.109 (4)	0.0028 (17)	−0.012 (2)	−0.020 (2)
C6	0.049 (2)	0.0323 (18)	0.102 (3)	−0.0017 (16)	−0.024 (2)	0.0034 (19)
C7	0.0375 (16)	0.0291 (15)	0.072 (2)	−0.0081 (14)	−0.0220 (15)	0.0086 (14)
C8	0.056 (2)	0.0424 (19)	0.066 (2)	−0.0207 (18)	−0.0305 (18)	0.0263 (17)
C9	0.058 (2)	0.053 (2)	0.0422 (17)	−0.0248 (18)	−0.0189 (15)	0.0198 (15)
C10	0.0468 (17)	0.0473 (18)	0.0349 (15)	−0.0174 (15)	−0.0096 (13)	0.0085 (13)
C11	0.0281 (13)	0.0308 (14)	0.0488 (17)	−0.0072 (12)	−0.0120 (12)	0.0040 (12)
C12	0.0283 (14)	0.0363 (16)	0.0495 (17)	−0.0077 (13)	−0.0038 (12)	−0.0068 (13)
C13	0.0310 (14)	0.0336 (14)	0.0322 (14)	−0.0119 (12)	−0.0064 (11)	0.0043 (11)
C14	0.0354 (15)	0.0400 (16)	0.0317 (14)	−0.0129 (13)	−0.0083 (11)	0.0036 (11)
C15	0.055 (2)	0.056 (2)	0.0391 (17)	0.0019 (17)	−0.0096 (15)	−0.0065 (15)
C16	0.070 (3)	0.073 (3)	0.0359 (18)	0.004 (2)	−0.0074 (17)	−0.0105 (17)
C17	0.059 (2)	0.071 (2)	0.0336 (16)	−0.016 (2)	−0.0111 (15)	0.0014 (16)
C18	0.0441 (18)	0.062 (2)	0.0440 (18)	−0.0004 (17)	−0.0145 (14)	0.0094 (16)
C19	0.0380 (16)	0.0506 (19)	0.0343 (15)	−0.0061 (15)	−0.0054 (12)	0.0017 (13)
C20	0.067 (3)	0.087 (3)	0.0363 (18)	−0.002 (2)	−0.0122 (17)	−0.0025 (18)
C21	0.0336 (14)	0.0362 (15)	0.0302 (14)	−0.0033 (12)	−0.0019 (11)	0.0075 (11)
C22	0.0382 (15)	0.0323 (15)	0.0317 (14)	−0.0043 (13)	−0.0003 (11)	0.0079 (11)
C23	0.0530 (19)	0.0413 (17)	0.0370 (16)	−0.0155 (15)	−0.0057 (13)	0.0109 (13)
C24	0.064 (2)	0.049 (2)	0.0328 (15)	−0.0188 (18)	−0.0092 (14)	0.0073 (13)
C25	0.062 (2)	0.0352 (16)	0.0314 (15)	−0.0059 (15)	−0.0002 (14)	0.0073 (12)
C26	0.079 (3)	0.0394 (18)	0.0404 (17)	−0.0179 (18)	−0.0041 (17)	0.0093 (14)
C27	0.067 (2)	0.0377 (17)	0.0386 (16)	−0.0162 (17)	−0.0052 (15)	0.0043 (13)
C28	0.068 (2)	0.0435 (18)	0.0340 (16)	−0.0062 (17)	−0.0052 (15)	0.0090 (13)

Geometric parameters (Å, º) top

Co1—O2	2.069 (2)	C8—H8A	0.9300
Co1—O4	2.105 (2)	C9—C10	1.400 (4)
Co1—O1W	2.109 (2)	C9—H9A	0.9300
Co1—N2	2.131 (2)	C10—H10A	0.9300
Co1—N1	2.132 (3)	C11—C12	1.430 (4)
Co1—O2W	2.145 (2)	C13—C14	1.499 (4)
O1W—H1W1	0.85 (1)	C14—C15	1.379 (5)
O1W—H1W2	0.85 (3)	C14—C19	1.386 (4)
O2W—H2W1	0.85 (1)	C15—C16	1.378 (5)
O2W—H2W2	0.856 (10)	C15—H15A	0.9300
O1—C21	1.246 (4)	C16—C17	1.379 (6)
O2—C21	1.263 (4)	C16—H16A	0.9300
O3—C13	1.259 (4)	C17—C18	1.393 (5)
O4—C13	1.257 (3)	C17—C20	1.485 (5)
N1—C1	1.319 (4)	C18—C19	1.385 (4)
N1—C12	1.360 (4)	C18—H18A	0.9300
N2—C10	1.331 (4)	C19—H19A	0.9300
N2—C11	1.354 (4)	C20—C20ⁱ	1.290 (8)
C1—C2	1.399 (5)	C20—H20A	0.9300
C1—H1A	0.9300	C21—C22	1.508 (4)
C2—C3	1.360 (6)	C22—C23	1.381 (5)
C2—H2A	0.9300	C22—C27	1.394 (4)
C3—C4	1.394 (6)	C23—C24	1.393 (4)
C3—H3A	0.9300	C23—H23A	0.9300
C4—C12	1.406 (5)	C24—C25	1.392 (5)
C4—C5	1.440 (6)	C24—H24A	0.9300
C5—C6	1.340 (6)	C25—C26	1.388 (5)
C5—H5A	0.9300	C25—C28	1.469 (4)
C6—C7	1.417 (5)	C26—C27	1.375 (4)
C6—H6A	0.9300	C26—H26A	0.9300
C7—C8	1.394 (5)	C27—H27A	0.9300
C7—C11	1.415 (4)	C28—C28ⁱⁱ	1.327 (7)
C8—C9	1.357 (5)	C28—H28A	0.9300

O2—Co1—O4	84.05 (8)	N2—C10—H10A	118.6
O2—Co1—O1W	92.31 (10)	C9—C10—H10A	118.6
O4—Co1—O1W	87.44 (9)	N2—C11—C7	122.9 (3)
O2—Co1—N2	169.76 (9)	N2—C11—C12	117.4 (3)
O4—Co1—N2	100.04 (9)	C7—C11—C12	119.7 (3)
O1W—Co1—N2	97.24 (10)	N1—C12—C4	123.2 (3)
O2—Co1—N1	93.57 (10)	N1—C12—C11	116.8 (3)
O4—Co1—N1	86.75 (9)	C4—C12—C11	120.0 (3)
O1W—Co1—N1	171.27 (10)	O4—C13—O3	123.8 (3)
N2—Co1—N1	77.39 (10)	O4—C13—C14	117.8 (3)
O2—Co1—O2W	87.87 (8)	O3—C13—C14	118.4 (3)
O4—Co1—O2W	169.94 (8)	C15—C14—C19	118.6 (3)
O1W—Co1—O2W	86.90 (9)	C15—C14—C13	119.6 (3)
N2—Co1—O2W	88.93 (9)	C19—C14—C13	121.8 (3)
N1—Co1—O2W	99.76 (9)	C16—C15—C14	120.9 (4)
Co1—O1W—H1W1	138 (3)	C16—C15—H15A	119.5
Co1—O1W—H1W2	100 (2)	C14—C15—H15A	119.5
H1W1—O1W—H1W2	110.2 (17)	C17—C16—C15	121.4 (4)
Co1—O2W—H2W1	117 (3)	C17—C16—H16A	119.3
Co1—O2W—H2W2	95 (2)	C15—C16—H16A	119.3
H2W1—O2W—H2W2	108.6 (16)	C16—C17—C18	117.5 (3)
C21—O2—Co1	129.21 (19)	C16—C17—C20	118.1 (4)
C13—O4—Co1	119.98 (18)	C18—C17—C20	124.3 (4)
C1—N1—C12	118.1 (3)	C19—C18—C17	121.3 (3)
C1—N1—Co1	127.6 (2)	C19—C18—H18A	119.4
C12—N1—Co1	114.2 (2)	C17—C18—H18A	119.4
C10—N2—C11	117.8 (3)	C18—C19—C14	120.2 (3)
C10—N2—Co1	128.1 (2)	C18—C19—H19A	119.9
C11—N2—Co1	114.14 (19)	C14—C19—H19A	119.9
N1—C1—C2	122.4 (4)	C20ⁱ—C20—C17	127.2 (5)
N1—C1—H1A	118.8	C20ⁱ—C20—H20A	116.4
C2—C1—H1A	118.8	C17—C20—H20A	116.4
C3—C2—C1	119.4 (4)	O1—C21—O2	126.3 (3)
C3—C2—H2A	120.3	O1—C21—C22	117.5 (3)
C1—C2—H2A	120.3	O2—C21—C22	116.2 (3)
C2—C3—C4	120.4 (4)	C23—C22—C27	119.4 (3)
C2—C3—H3A	119.8	C23—C22—C21	121.2 (3)
C4—C3—H3A	119.8	C27—C22—C21	119.3 (3)
C3—C4—C12	116.5 (4)	C22—C23—C24	119.9 (3)
C3—C4—C5	125.0 (4)	C22—C23—H23A	120.1
C12—C4—C5	118.5 (4)	C24—C23—H23A	120.1
C6—C5—C4	121.0 (4)	C25—C24—C23	121.0 (3)
C6—C5—H5A	119.5	C25—C24—H24A	119.5
C4—C5—H5A	119.5	C23—C24—H24A	119.5
C5—C6—C7	122.1 (4)	C26—C25—C24	118.0 (3)
C5—C6—H6A	119.0	C26—C25—C28	122.3 (3)
C7—C6—H6A	119.0	C24—C25—C28	119.6 (3)
C8—C7—C11	117.0 (3)	C27—C26—C25	121.4 (3)
C8—C7—C6	124.3 (3)	C27—C26—H26A	119.3
C11—C7—C6	118.7 (3)	C25—C26—H26A	119.3
C9—C8—C7	120.2 (3)	C26—C27—C22	120.2 (3)
C9—C8—H8A	119.9	C26—C27—H27A	119.9
C7—C8—H8A	119.9	C22—C27—H27A	119.9
C8—C9—C10	119.2 (3)	C28ⁱⁱ—C28—C25	125.9 (5)
C8—C9—H9A	120.4	C28ⁱⁱ—C28—H28A	117.1
C10—C9—H9A	120.4	C25—C28—H28A	117.1
N2—C10—C9	122.9 (3)

O4—Co1—O2—C21	−157.9 (3)	C8—C7—C11—C12	−179.0 (3)
O1W—Co1—O2—C21	−70.7 (3)	C6—C7—C11—C12	−0.1 (4)
N2—Co1—O2—C21	88.0 (6)	C1—N1—C12—C4	−0.9 (4)
N1—Co1—O2—C21	115.8 (3)	Co1—N1—C12—C4	−177.4 (2)
O2W—Co1—O2—C21	16.1 (3)	C1—N1—C12—C11	178.4 (3)
O2—Co1—O4—C13	51.2 (2)	Co1—N1—C12—C11	1.9 (3)
O1W—Co1—O4—C13	−41.4 (2)	C3—C4—C12—N1	−0.4 (5)
N2—Co1—O4—C13	−138.3 (2)	C5—C4—C12—N1	178.9 (3)
N1—Co1—O4—C13	145.2 (2)	C3—C4—C12—C11	−179.7 (3)
O2W—Co1—O4—C13	14.5 (5)	C5—C4—C12—C11	−0.3 (5)
O2—Co1—N1—C1	6.0 (3)	N2—C11—C12—N1	1.0 (4)
O4—Co1—N1—C1	−77.8 (3)	C7—C11—C12—N1	−178.9 (3)
N2—Co1—N1—C1	−178.8 (3)	N2—C11—C12—C4	−179.7 (3)
O2W—Co1—N1—C1	94.5 (3)	C7—C11—C12—C4	0.4 (4)
O2—Co1—N1—C12	−177.9 (2)	Co1—O4—C13—O3	63.9 (3)
O4—Co1—N1—C12	98.3 (2)	Co1—O4—C13—C14	−114.4 (2)
N2—Co1—N1—C12	−2.8 (2)	O4—C13—C14—C15	−8.7 (4)
O2W—Co1—N1—C12	−89.5 (2)	O3—C13—C14—C15	172.8 (3)
O2—Co1—N2—C10	−150.0 (4)	O4—C13—C14—C19	168.4 (3)
O4—Co1—N2—C10	97.2 (3)	O3—C13—C14—C19	−10.0 (4)
O1W—Co1—N2—C10	8.5 (3)	C19—C14—C15—C16	0.8 (5)
N1—Co1—N2—C10	−178.5 (3)	C13—C14—C15—C16	178.1 (3)
O2W—Co1—N2—C10	−78.2 (3)	C14—C15—C16—C17	0.1 (7)
O2—Co1—N2—C11	31.8 (6)	C15—C16—C17—C18	−1.3 (6)
O4—Co1—N2—C11	−81.0 (2)	C15—C16—C17—C20	179.4 (4)
O1W—Co1—N2—C11	−169.68 (19)	C16—C17—C18—C19	1.6 (6)
N1—Co1—N2—C11	3.33 (19)	C20—C17—C18—C19	−179.1 (4)
O2W—Co1—N2—C11	103.58 (19)	C17—C18—C19—C14	−0.7 (6)
C12—N1—C1—C2	1.2 (5)	C15—C14—C19—C18	−0.5 (5)
Co1—N1—C1—C2	177.2 (3)	C13—C14—C19—C18	−177.7 (3)
N1—C1—C2—C3	−0.3 (6)	C16—C17—C20—C20ⁱ	−177.1 (6)
C1—C2—C3—C4	−1.1 (6)	C18—C17—C20—C20ⁱ	3.6 (9)
C2—C3—C4—C12	1.4 (6)	Co1—O2—C21—O1	3.4 (5)
C2—C3—C4—C5	−177.9 (4)	Co1—O2—C21—C22	−174.32 (19)
C3—C4—C5—C6	179.2 (4)	O1—C21—C22—C23	176.1 (3)
C12—C4—C5—C6	−0.1 (5)	O2—C21—C22—C23	−6.0 (4)
C4—C5—C6—C7	0.4 (6)	O1—C21—C22—C27	−6.3 (4)
C5—C6—C7—C8	178.5 (4)	O2—C21—C22—C27	171.6 (3)
C5—C6—C7—C11	−0.3 (5)	C27—C22—C23—C24	−0.7 (5)
C11—C7—C8—C9	−0.3 (5)	C21—C22—C23—C24	176.9 (3)
C6—C7—C8—C9	−179.0 (3)	C22—C23—C24—C25	−1.3 (6)
C7—C8—C9—C10	0.3 (5)	C23—C24—C25—C26	1.6 (6)
C11—N2—C10—C9	2.0 (4)	C23—C24—C25—C28	−178.1 (3)
Co1—N2—C10—C9	−176.2 (2)	C24—C25—C26—C27	0.0 (6)
C8—C9—C10—N2	−1.2 (5)	C28—C25—C26—C27	179.7 (4)
C10—N2—C11—C7	−1.9 (4)	C25—C26—C27—C22	−2.0 (6)
Co1—N2—C11—C7	176.5 (2)	C23—C22—C27—C26	2.3 (5)
C10—N2—C11—C12	178.1 (3)	C21—C22—C27—C26	−175.4 (3)
Co1—N2—C11—C12	−3.5 (3)	C26—C25—C28—C28ⁱⁱ	−14.3 (7)
C8—C7—C11—N2	1.1 (4)	C24—C25—C28—C28ⁱⁱ	165.4 (5)
C6—C7—C11—N2	180.0 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2Wⁱⁱⁱ	0.85 (1)	1.90 (1)	2.749 (3)	177 (4)
O1W—H1W2···O3	0.85 (3)	1.83 (3)	2.653 (3)	164 (3)
O2W—H2W1···O3^iv	0.85 (1)	1.83 (3)	2.679 (3)	172 (3)
O2W—H2W2···O1	0.86 (1)	1.72 (3)	2.564 (3)	169 (4)
O2W—H2W2···O2	0.86 (1)	2.51 (4)	2.925 (3)	111 (3)

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

Experimental details

Crystal data
Chemical formula	[Co(C₁₆H₁₀O₄)(C₁₂H₈N₂)H₂O)₂]
M_r	541.41
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.5345 (15), 9.2112 (18), 18.524 (4)
α, β, γ (°)	88.12 (3), 84.29 (3), 76.38 (3)
V (Å³)	1243.2 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.74
Crystal size (mm)	0.36 × 0.24 × 0.12

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.811, 0.917
No. of measured, independent and observed [I > 2σ(I)] reflections	11895, 5509, 4338
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.142, 1.01
No. of reflections	5509
No. of parameters	346
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.48

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), publCIF (Westrip 2007).

Selected geometric parameters (Å, º) top

Co1—O2	2.069 (2)	Co1—N2	2.131 (2)
Co1—O4	2.105 (2)	Co1—N1	2.132 (3)
Co1—O1W	2.109 (2)	Co1—O2W	2.145 (2)

O2—Co1—O4	84.05 (8)	O1W—Co1—N1	171.27 (10)
O2—Co1—O1W	92.31 (10)	N2—Co1—N1	77.39 (10)
O4—Co1—O1W	87.44 (9)	O2—Co1—O2W	87.87 (8)
O2—Co1—N2	169.76 (9)	O4—Co1—O2W	169.94 (8)
O4—Co1—N2	100.04 (9)	O1W—Co1—O2W	86.90 (9)
O1W—Co1—N2	97.24 (10)	N2—Co1—O2W	88.93 (9)
O2—Co1—N1	93.57 (10)	N1—Co1—O2W	99.76 (9)
O4—Co1—N1	86.75 (9)