(5,5'-Dicarboxy-biphenyl-2,2'-dicarboxyl-ato-κO,O)bis-(1,10-phenanthroline-κN,N')cobalt(II) dihydrate.

In the title compound, [Co(C(16)H(8)O(8))(C(12)H(8)N(2))(2)]·2H(2)O, the Co atom located on a twofold rotation axis. It is six-coordinated by two O atoms from one 5,5'-dicarboxy-biphenyl-2,2'-dicarboxyl-ate anion and four N atoms from two 1,10-phenanthroline mol-ecules in a distorted octa-hedral environment. The crystal packing is stabilized by O-H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

[Co(C16H8O8)(C12H8N2)2]·2H2O

M = 783.59

Monoclinic,

a = 16.9272 (14) Å

b = 9.4514 (8) Å

c = 22.0458 (19) Å

β = 96.056 (1)°

V = 3507.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.56 mm−1

T = 293 (2) K

0.28 × 0.25 × 0.23 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.852, T max = 0.880

9540 measured reflections

3447 independent reflections

2705 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.111

S = 1.05

3447 reflections

255 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.21 e Å−3

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801012X/bt2694sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801012X/bt2694Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Co(C16H8O8)(C12H8N2)2]·2H2O	F000 = 1612
Mr = 783.59	Dx = 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 = 2.0–26.0º
b = 9.4514 (8) Å	µ = 0.56 mm−1
c = 22.0458 (19) Å	T = 293 (2) K
β = 96.0560 (10)º	Block, pink
V = 3507.3 (5) Å3	0.28 × 0.25 × 0.23 mm
Z = 4

Bruker APEX CCD area-detector diffractometer	3447 independent reflections
Radiation source: fine-focus sealed tube	2705 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.039
T = 293(2) K	θmax = 26.0º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 1998)	h = −20→20
Tmin = 0.852, Tmax = 0.880	k = −11→10
9540 measured reflections	l = −27→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0514P)2 + 0.7022P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3447 reflections	Δρmax = 0.43 e Å−3
255 parameters	Δρmin = −0.21 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
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*

	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

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)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O2	0.890 (10)	1.929 (11)	2.811 (3)	171 (3)
O4—H4···O2ii	0.82	1.74	2.535 (2)	163
O1W—H1B···O3iii	0.889 (10)	2.177 (19)	2.934 (3)	143 (2)

Table 1

Selected bond lengths (Å)

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

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O2	0.890 (10)	1.929 (11)	2.811 (3)	171 (3)
O4—H4⋯O2i	0.82	1.74	2.535 (2)	163
O1W—H1B⋯O3ii	0.889 (10)	2.177 (19)	2.934 (3)	143 (2)

Symmetry codes: (i) ; (ii) .