(5,5′-Dicarboxy­biphenyl-2,2′-dicarboxyl­ato-κ2O2,O2′)bis­(1,10-phenanthroline-κ2N,N′)cobalt(II) dihydrate

Chen, R.; Guo, F.; Meng, F.

doi:10.1107/S160053680801012X

(5,5′-Dicarboxybiphenyl-2,2′-dicarboxylato-κ²O²,O^2′)bis(1,10-phenanthroline-κ²N,N′)cobalt(II) dihydrate

In the title compound, [Co(C₁₆H₈O₈)(C₁₂H₈N₂)₂]·2H₂O, the Co atom located on a twofold rotation axis. It is six-coordinated by two O atoms from one 5,5′-dicarboxybiphenyl-2,2′-dicarboxylate anion and four N atoms from two 1,10-phenanthroline molecules in a distorted octahedral environment. The crystal packing is stabilized by O—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680801012X/bt2694sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680801012X/bt2694Isup2.hkl Contains datablock I

CCDC reference: 690812

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.048
wR factor = 0.111
Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.70 Ratio

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.06
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.12 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11    -   C12     ..       5.21 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.07

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

   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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Aromatic polycarboxylate ligands have been extensively employed in the preparation of metal-organic coordination complexes due to their ability to form networks and due to their interesting properties (Lehn, 1990; Che et al., 2006). We selected biphenyl-2,5,2',5'-tetracarboxylic acid (H₄BPTC) as a bridging ligand, 1,10-phenanthroline as a neutral ligand, and Co^II as a metal center, in order to generate a new compound, [Co(H₂BPTC)(Phen)₂]^.2H₂O, (I), which is reported here.

In compound (I), each Co^II atom is six-coordinated by two O atoms from one H₂BPTC anion and four N atoms from two 1,10-phenanthroline molecules in a distorted octahedral environment (Fig. 1). The bond lengths are all within the normal ranges (Zang et al., 2006). The crystal packing is stabilized by O—H···O hydrogen bonds between carboxylate groups and water molecules.

Related literature top

For related literature, see: Zang et al. (2006); Che et al. (2006); Lehn (1990).

Experimental top

A mixture of CoCl₂^.2H₂O (0.1 mmol), biphenyl-2,5,2',5'-tetracarboxylic acid (0.2 mmol), 1,10-phenanthroline (0.2 mmol) and H₂O(15 ml) in a 25 ml stainless steel reactor with a Teflon liner was heated from 298 to 443 K in 2 h and a constant temperature was maintained at 443 K for 72 h, after which the mixture was cooled to 298 K. Then, pink crystals of were obtained.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The structure of (I), showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Symmetry code: (i) -x, y, 0.5 - z.

(5,5'-Dicarboxybiphenyl-2,2'-dicarboxylato-κ²O²,O^2')bis(1,10- phenanthroline-κ²N,N')cobalt(II) dihydrate top

Crystal data top

[Co(C₁₆H₈O₈)(C₁₂H₈N₂)₂]·2H₂O	F(000) = 1612
M_r = 783.59	D_x = 1.484 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3447 reflections
a = 16.9272 (14) Å	θ = 2.0–26.0°
b = 9.4514 (8) Å	µ = 0.56 mm⁻¹
c = 22.0458 (19) Å	T = 293 K
β = 96.056 (1)°	Block, pink
V = 3507.3 (5) Å³	0.28 × 0.25 × 0.23 mm
Z = 4

Data collection top

Bruker APEX CCD area-detector diffractometer	3447 independent reflections
Radiation source: fine-focus sealed tube	2705 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −20→20
T_min = 0.852, T_max = 0.880	k = −11→10
9540 measured reflections	l = −27→22

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) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0514P)² + 0.7022P] where P = (F_o² + 2F_c²)/3
3447 reflections	(Δ/σ)_max < 0.001
255 parameters	Δρ_max = 0.43 e Å⁻³
2 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

[Co(C₁₆H₈O₈)(C₁₂H₈N₂)₂]·2H₂O	V = 3507.3 (5) Å³
M_r = 783.59	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 16.9272 (14) Å	µ = 0.56 mm⁻¹
b = 9.4514 (8) Å	T = 293 K
c = 22.0458 (19) Å	0.28 × 0.25 × 0.23 mm
β = 96.056 (1)°

Data collection top

Bruker APEX CCD area-detector diffractometer	3447 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	2705 reflections with I > 2σ(I)
T_min = 0.852, T_max = 0.880	R_int = 0.039
9540 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	2 restraints
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.43 e Å⁻³
3447 reflections	Δρ_min = −0.21 e Å⁻³
255 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
C1	0.02180 (12)	0.3926 (2)	0.17029 (10)	0.0195 (5)
C2	−0.01759 (12)	0.4503 (2)	0.21744 (10)	0.0176 (5)
C3	−0.08951 (13)	0.5192 (2)	0.20193 (10)	0.0210 (5)
H3	−0.1170	0.5561	0.2327	0.025*
C4	−0.12130 (13)	0.5340 (3)	0.14147 (11)	0.0240 (5)
C5	−0.07984 (13)	0.4819 (3)	0.09534 (11)	0.0281 (6)
H5	−0.0999	0.4935	0.0547	0.034*
C6	−0.00843 (13)	0.4127 (3)	0.11002 (11)	0.0265 (6)
H6	0.0197	0.3791	0.0790	0.032*
C7	0.09258 (13)	0.2983 (2)	0.18419 (11)	0.0227 (5)
C8	−0.19930 (14)	0.6078 (3)	0.12529 (11)	0.0305 (6)
C9	0.12655 (16)	0.1382 (3)	0.36037 (13)	0.0419 (7)
H9	0.1462	0.2070	0.3358	0.050*
C10	0.16476 (18)	0.1183 (4)	0.41931 (15)	0.0551 (9)
H10	0.2081	0.1740	0.4335	0.066*
C11	0.13745 (19)	0.0158 (4)	0.45565 (15)	0.0579 (10)
H11	0.1632	−0.0008	0.4944	0.069*
C12	0.07085 (19)	−0.0637 (3)	0.43443 (14)	0.0463 (8)
C13	0.03635 (17)	−0.0368 (3)	0.37519 (13)	0.0369 (7)
C14	−0.03385 (18)	−0.1126 (3)	0.35129 (13)	0.0393 (7)
C15	−0.0675 (2)	−0.2122 (3)	0.38854 (15)	0.0500 (8)
C16	−0.0295 (3)	−0.2393 (4)	0.44813 (17)	0.0651 (11)
H16	−0.0508	−0.3072	0.4723	0.078*
C17	0.0364 (2)	−0.1692 (4)	0.47042 (16)	0.0637 (10)
H17	0.0598	−0.1893	0.5095	0.076*
C18	−0.1378 (2)	−0.2783 (3)	0.36436 (17)	0.0612 (10)
H18	−0.1619	−0.3455	0.3871	0.073*
C19	−0.1707 (2)	−0.2438 (3)	0.30749 (17)	0.0573 (10)
H19	−0.2184	−0.2849	0.2915	0.069*
C20	−0.13227 (18)	−0.1458 (3)	0.27306 (15)	0.0472 (8)
H20	−0.1551	−0.1239	0.2339	0.057*
N1	0.06377 (12)	0.0635 (2)	0.33797 (10)	0.0342 (5)
N2	−0.06511 (14)	−0.0830 (2)	0.29367 (11)	0.0369 (6)
O1	0.09051 (9)	0.20921 (16)	0.22641 (7)	0.0257 (4)
O2	0.14953 (10)	0.3116 (2)	0.15270 (8)	0.0443 (5)
O1W	0.16597 (12)	0.4484 (2)	0.04153 (9)	0.0432 (5)
O3	−0.22748 (11)	0.6294 (2)	0.07347 (8)	0.0507 (6)
O4	−0.23287 (10)	0.6461 (2)	0.17334 (8)	0.0475 (6)
H4	−0.2751	0.6858	0.1626	0.071*
Co1	0.0000	0.07672 (5)	0.2500	0.02804 (17)
H1A	0.1647 (16)	0.398 (3)	0.0755 (8)	0.042*
H1B	0.1857 (15)	0.388 (2)	0.0163 (10)	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0143 (10)	0.0227 (13)	0.0218 (12)	0.0028 (9)	0.0030 (9)	0.0004 (10)
C2	0.0153 (11)	0.0177 (12)	0.0199 (12)	−0.0020 (9)	0.0029 (9)	0.0005 (9)
C3	0.0181 (11)	0.0248 (13)	0.0203 (13)	0.0026 (9)	0.0033 (10)	−0.0037 (10)
C4	0.0193 (12)	0.0288 (14)	0.0238 (13)	0.0063 (10)	0.0016 (10)	0.0001 (10)
C5	0.0236 (12)	0.0418 (16)	0.0180 (13)	0.0087 (11)	−0.0021 (10)	0.0010 (11)
C6	0.0245 (12)	0.0360 (15)	0.0196 (13)	0.0085 (11)	0.0058 (10)	−0.0030 (11)
C7	0.0198 (12)	0.0260 (13)	0.0222 (13)	0.0052 (10)	0.0019 (10)	−0.0028 (10)
C8	0.0227 (12)	0.0443 (17)	0.0242 (14)	0.0110 (11)	0.0020 (11)	0.0005 (12)
C9	0.0319 (15)	0.0500 (18)	0.0444 (18)	0.0084 (14)	0.0072 (13)	0.0125 (14)
C10	0.0368 (16)	0.079 (3)	0.048 (2)	0.0138 (16)	−0.0001 (15)	0.0097 (18)
C11	0.051 (2)	0.081 (3)	0.0416 (19)	0.0279 (19)	0.0070 (16)	0.0244 (18)
C12	0.0533 (19)	0.0457 (19)	0.0425 (18)	0.0193 (15)	0.0168 (15)	0.0117 (15)
C13	0.0483 (17)	0.0286 (15)	0.0371 (17)	0.0160 (13)	0.0195 (14)	0.0069 (12)
C14	0.0587 (19)	0.0238 (15)	0.0404 (17)	0.0087 (13)	0.0283 (15)	0.0025 (12)
C15	0.079 (2)	0.0265 (16)	0.051 (2)	0.0043 (16)	0.0385 (18)	0.0022 (14)
C16	0.106 (3)	0.038 (2)	0.060 (2)	0.007 (2)	0.048 (2)	0.0151 (17)
C17	0.092 (3)	0.055 (2)	0.049 (2)	0.026 (2)	0.029 (2)	0.0256 (18)
C18	0.094 (3)	0.0323 (18)	0.067 (3)	−0.0128 (18)	0.056 (2)	−0.0067 (16)
C19	0.074 (2)	0.0376 (18)	0.068 (2)	−0.0217 (17)	0.043 (2)	−0.0196 (17)
C20	0.060 (2)	0.0317 (16)	0.054 (2)	−0.0110 (15)	0.0279 (16)	−0.0119 (14)
N1	0.0352 (12)	0.0323 (13)	0.0367 (13)	0.0091 (10)	0.0119 (10)	0.0061 (10)
N2	0.0485 (14)	0.0236 (12)	0.0426 (14)	−0.0036 (11)	0.0238 (12)	−0.0048 (10)
O1	0.0231 (9)	0.0249 (9)	0.0294 (10)	0.0044 (7)	0.0038 (7)	0.0069 (8)
O2	0.0297 (10)	0.0664 (14)	0.0402 (12)	0.0286 (9)	0.0196 (9)	0.0277 (10)
O1W	0.0472 (12)	0.0570 (14)	0.0262 (11)	0.0127 (10)	0.0079 (9)	0.0085 (9)
O3	0.0378 (11)	0.0889 (17)	0.0242 (11)	0.0349 (11)	−0.0027 (9)	0.0028 (10)
O4	0.0356 (11)	0.0810 (15)	0.0264 (10)	0.0384 (10)	0.0057 (9)	0.0074 (10)
Co1	0.0308 (3)	0.0225 (3)	0.0323 (3)	0.000	0.0103 (2)	0.000

Geometric parameters (Å, º) top

C1—C6	1.385 (3)	C13—N1	1.367 (3)
C1—C2	1.403 (3)	C13—C14	1.439 (4)
C1—C7	1.499 (3)	C14—N2	1.353 (4)
C2—C3	1.391 (3)	C14—C15	1.408 (4)
C2—C2ⁱ	1.495 (4)	C15—C18	1.399 (5)
C3—C4	1.391 (3)	C15—C16	1.424 (5)
C3—H3	0.9300	C16—C17	1.345 (5)
C4—C5	1.385 (3)	C16—H16	0.9300
C4—C8	1.503 (3)	C17—H17	0.9300
C5—C6	1.382 (3)	C18—C19	1.357 (5)
C5—H5	0.9300	C18—H18	0.9300
C6—H6	0.9300	C19—C20	1.401 (4)
C7—O2	1.252 (3)	C19—H19	0.9300
C7—O1	1.258 (3)	C20—N2	1.320 (4)
C8—O3	1.208 (3)	C20—H20	0.9300
C8—O4	1.305 (3)	N1—Co1	2.121 (2)
C9—N1	1.327 (3)	N2—Co1	2.155 (2)
C9—C10	1.402 (4)	O1—Co1	2.0865 (16)
C9—H9	0.9300	O1W—H1A	0.890 (10)
C10—C11	1.368 (4)	O1W—H1B	0.889 (10)
C10—H10	0.9300	O4—H4	0.8200
C11—C12	1.394 (5)	Co1—O1ⁱ	2.0865 (16)
C11—H11	0.9300	Co1—N1ⁱ	2.121 (2)
C12—C13	1.396 (4)	Co1—N2ⁱ	2.155 (2)
C12—C17	1.437 (4)

C6—C1—C2	120.1 (2)	C18—C15—C14	117.2 (3)
C6—C1—C7	118.9 (2)	C18—C15—C16	123.7 (3)
C2—C1—C7	120.8 (2)	C14—C15—C16	119.2 (3)
C3—C2—C1	118.1 (2)	C17—C16—C15	121.7 (3)
C3—C2—C2ⁱ	119.1 (2)	C17—C16—H16	119.2
C1—C2—C2ⁱ	122.6 (2)	C15—C16—H16	119.2
C2—C3—C4	121.5 (2)	C16—C17—C12	120.7 (3)
C2—C3—H3	119.2	C16—C17—H17	119.7
C4—C3—H3	119.2	C12—C17—H17	119.7
C5—C4—C3	119.5 (2)	C19—C18—C15	119.6 (3)
C5—C4—C8	119.4 (2)	C19—C18—H18	120.2
C3—C4—C8	121.0 (2)	C15—C18—H18	120.2
C6—C5—C4	119.6 (2)	C18—C19—C20	119.4 (3)
C6—C5—H5	120.2	C18—C19—H19	120.3
C4—C5—H5	120.2	C20—C19—H19	120.3
C5—C6—C1	121.0 (2)	N2—C20—C19	122.9 (3)
C5—C6—H6	119.5	N2—C20—H20	118.5
C1—C6—H6	119.5	C19—C20—H20	118.5
O2—C7—O1	124.1 (2)	C9—N1—C13	117.1 (2)
O2—C7—C1	118.2 (2)	C9—N1—Co1	128.26 (19)
O1—C7—C1	117.7 (2)	C13—N1—Co1	114.67 (19)
O3—C8—O4	124.0 (2)	C20—N2—C14	117.9 (3)
O3—C8—C4	123.5 (2)	C20—N2—Co1	128.6 (2)
O4—C8—C4	112.5 (2)	C14—N2—Co1	113.37 (18)
N1—C9—C10	123.2 (3)	C7—O1—Co1	131.64 (15)
N1—C9—H9	118.4	H1A—O1W—H1B	103 (3)
C10—C9—H9	118.4	C8—O4—H4	109.5
C11—C10—C9	119.1 (3)	O1—Co1—O1ⁱ	106.24 (9)
C11—C10—H10	120.5	O1—Co1—N1ⁱ	97.10 (7)
C9—C10—H10	120.5	O1ⁱ—Co1—N1ⁱ	86.97 (7)
C10—C11—C12	119.8 (3)	O1—Co1—N1	86.97 (7)
C10—C11—H11	120.1	O1ⁱ—Co1—N1	97.10 (7)
C12—C11—H11	120.1	N1ⁱ—Co1—N1	173.25 (12)
C11—C12—C13	117.4 (3)	O1—Co1—N2	162.80 (8)
C11—C12—C17	123.4 (3)	O1ⁱ—Co1—N2	83.42 (7)
C13—C12—C17	119.2 (3)	N1ⁱ—Co1—N2	97.60 (9)
N1—C13—C12	123.5 (3)	N1—Co1—N2	77.60 (9)
N1—C13—C14	116.4 (3)	O1—Co1—N2ⁱ	83.42 (7)
C12—C13—C14	120.0 (3)	O1ⁱ—Co1—N2ⁱ	162.80 (8)
N2—C14—C15	122.9 (3)	N1ⁱ—Co1—N2ⁱ	77.60 (9)
N2—C14—C13	117.8 (2)	N1—Co1—N2ⁱ	97.60 (8)
C15—C14—C13	119.2 (3)	N2—Co1—N2ⁱ	91.07 (11)

C6—C1—C2—C3	4.1 (3)	C14—C15—C18—C19	−0.7 (4)
C7—C1—C2—C3	−170.5 (2)	C16—C15—C18—C19	178.7 (3)
C6—C1—C2—C2ⁱ	−171.09 (18)	C15—C18—C19—C20	2.1 (5)
C7—C1—C2—C2ⁱ	14.4 (3)	C18—C19—C20—N2	−0.8 (5)
C1—C2—C3—C4	−1.4 (3)	C10—C9—N1—C13	0.0 (4)
C2ⁱ—C2—C3—C4	173.90 (19)	C10—C9—N1—Co1	−178.9 (2)
C2—C3—C4—C5	−1.4 (4)	C12—C13—N1—C9	0.0 (4)
C2—C3—C4—C8	179.6 (2)	C14—C13—N1—C9	177.3 (2)
C3—C4—C5—C6	1.7 (4)	C12—C13—N1—Co1	179.0 (2)
C8—C4—C5—C6	−179.4 (2)	C14—C13—N1—Co1	−3.6 (3)
C4—C5—C6—C1	1.0 (4)	C19—C20—N2—C14	−1.9 (4)
C2—C1—C6—C5	−3.9 (4)	C19—C20—N2—Co1	−176.8 (2)
C7—C1—C6—C5	170.7 (2)	C15—C14—N2—C20	3.4 (4)
C6—C1—C7—O2	45.0 (3)	C13—C14—N2—C20	−175.8 (2)
C2—C1—C7—O2	−140.4 (2)	C15—C14—N2—Co1	179.0 (2)
C6—C1—C7—O1	−134.1 (2)	C13—C14—N2—Co1	−0.1 (3)
C2—C1—C7—O1	40.5 (3)	O2—C7—O1—Co1	−137.2 (2)
C5—C4—C8—O3	−2.7 (4)	C1—C7—O1—Co1	41.8 (3)
C3—C4—C8—O3	176.3 (3)	C7—O1—Co1—O1ⁱ	−63.12 (19)
C5—C4—C8—O4	177.5 (2)	C7—O1—Co1—N1ⁱ	25.8 (2)
C3—C4—C8—O4	−3.6 (3)	C7—O1—Co1—N1	−159.6 (2)
N1—C9—C10—C11	1.1 (5)	C7—O1—Co1—N2	174.4 (2)
C9—C10—C11—C12	−2.1 (5)	C7—O1—Co1—N2ⁱ	102.3 (2)
C10—C11—C12—C13	2.0 (4)	C9—N1—Co1—O1	9.2 (2)
C10—C11—C12—C17	−177.4 (3)	C13—N1—Co1—O1	−169.69 (17)
C11—C12—C13—N1	−0.9 (4)	C9—N1—Co1—O1ⁱ	−96.8 (2)
C17—C12—C13—N1	178.5 (3)	C13—N1—Co1—O1ⁱ	84.31 (17)
C11—C12—C13—C14	−178.3 (2)	C9—N1—Co1—N2	−178.4 (2)
C17—C12—C13—C14	1.2 (4)	C13—N1—Co1—N2	2.68 (17)
N1—C13—C14—N2	2.5 (3)	C9—N1—Co1—N2ⁱ	92.2 (2)
C12—C13—C14—N2	180.0 (2)	C13—N1—Co1—N2ⁱ	−86.74 (17)
N1—C13—C14—C15	−176.7 (2)	C20—N2—Co1—O1	−159.6 (2)
C12—C13—C14—C15	0.8 (4)	C14—N2—Co1—O1	25.3 (3)
N2—C14—C15—C18	−2.1 (4)	C20—N2—Co1—O1ⁱ	75.0 (2)
C13—C14—C15—C18	177.0 (2)	C14—N2—Co1—O1ⁱ	−100.13 (17)
N2—C14—C15—C16	178.4 (3)	C20—N2—Co1—N1ⁱ	−11.1 (2)
C13—C14—C15—C16	−2.4 (4)	C14—N2—Co1—N1ⁱ	173.83 (17)
C18—C15—C16—C17	−177.4 (3)	C20—N2—Co1—N1	173.8 (2)
C14—C15—C16—C17	2.1 (5)	C14—N2—Co1—N1	−1.35 (17)
C15—C16—C17—C12	0.0 (5)	C20—N2—Co1—N2ⁱ	−88.7 (2)
C11—C12—C17—C16	177.8 (3)	C14—N2—Co1—N2ⁱ	96.20 (19)
C13—C12—C17—C16	−1.6 (5)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O2	0.89 (1)	1.93 (1)	2.811 (3)	171 (3)
O4—H4···O2ⁱⁱ	0.82	1.74	2.535 (2)	163
O1W—H1B···O3ⁱⁱⁱ	0.89 (1)	2.18 (2)	2.934 (3)	143 (2)

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

Experimental details

Crystal data
Chemical formula	[Co(C₁₆H₈O₈)(C₁₂H₈N₂)₂]·2H₂O
M_r	783.59
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	16.9272 (14), 9.4514 (8), 22.0458 (19)
β (°)	96.056 (1)
V (Å³)	3507.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.56
Crystal size (mm)	0.28 × 0.25 × 0.23

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.852, 0.880
No. of measured, independent and observed [I > 2σ(I)] reflections	9540, 3447, 2705
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.111, 1.05
No. of reflections	3447
No. of parameters	255
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.21

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

N1—Co1	2.121 (2)	Co1—O1ⁱ	2.0865 (16)
N2—Co1	2.155 (2)	Co1—N1ⁱ	2.121 (2)
O1—Co1	2.0865 (16)	Co1—N2ⁱ	2.155 (2)