catena-Poly[[(2,9-dimethyl-1,10-phenanthroline-κN,N')cobalt(II)]-μ-malonato-κO,O:O,O].

In the title compound, [Co(C(3)H(2)O(4))(C(14)H(12)N(2))](n), the Co(II) ion is in a distorted octa-hedral coordination being chelated by a 2,9-dimethyl-1,10-phenanthroline mol-ecule (dmphen) and two carboxyl-ate groups of two malonate ligands The malonate ligand acts in a bridging mode, forming coordination chains along [100]. π-π stacking inter-actions between dmphen ligands [inter-planar distances = 3.414 (4) and 3.447 (4) Å] organize the coordination polymers into supra-molecular double chains.

Related literature

For coordination polymers with dicarboxyl­ate ligands, see: Rao et al. (2004 ▶); Zheng et al. (2004 ▶).

Experimental

Crystal data

[Co(C3H2O4)(C14H12N2)]

M = 369.23

Triclinic,

a = 6.8767 (14) Å

b = 9.5293 (19) Å

c = 11.149 (2) Å

α = 86.83 (3)°

β = 89.53 (3)°

γ = 89.52 (3)°

V = 729.4 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.20 mm−1

T = 295 K

0.33 × 0.11 × 0.07 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.653, T max = 0.782

7245 measured reflections

3309 independent reflections

2590 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.127

S = 1.06

3309 reflections

222 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.40 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038043/gk2299sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038043/gk2299Isup2.hkl

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

[Co(C3H2O4)(C14H12N2)]	Z = 2
Mr = 369.23	F(000) = 378
Triclinic, P1	Dx = 1.681 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8767 (14) Å	Cell parameters from 5667 reflections
b = 9.5293 (19) Å	θ = 3.5–27.5°
c = 11.149 (2) Å	µ = 1.20 mm−1
α = 86.83 (3)°	T = 295 K
β = 89.53 (3)°	Plate, red
γ = 89.52 (3)°	0.33 × 0.11 × 0.07 mm
V = 729.4 (2) Å3

Rigaku R-AXIS RAPID diffractometer	3309 independent reflections
Radiation source: fine-focus sealed tube	2590 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 0 pixels mm-1	θmax = 27.5°, θmin = 3.5°
ω scans	h = −8→8
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −12→12
Tmin = 0.653, Tmax = 0.782	l = −14→14
7245 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0568P)2 + 0.8449P] where P = (Fo2 + 2Fc2)/3
3309 reflections	(Δ/σ)max = 0.015
222 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

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
Co1	0.23932 (7)	0.27775 (5)	0.73432 (4)	0.03063 (16)
N1	0.2539 (4)	0.0677 (3)	0.6805 (2)	0.0283 (6)
N2	0.2379 (4)	0.1661 (3)	0.9024 (2)	0.0264 (5)
C1	0.2526 (5)	0.0223 (4)	0.5691 (3)	0.0346 (7)
C2	0.2653 (5)	−0.1224 (4)	0.5494 (4)	0.0435 (9)
H2A	0.2659	−0.1521	0.4713	0.052*
C3	0.2765 (5)	−0.2181 (4)	0.6433 (4)	0.0439 (9)
H3A	0.2860	−0.3133	0.6297	0.053*
C4	0.2737 (5)	−0.1737 (3)	0.7614 (3)	0.0347 (7)
C5	0.2824 (5)	−0.2671 (4)	0.8659 (4)	0.0437 (9)
H5A	0.2923	−0.3633	0.8571	0.052*
C6	0.2766 (5)	−0.2182 (4)	0.9773 (4)	0.0413 (9)
H6A	0.2831	−0.2812	1.0439	0.050*
C7	0.2604 (5)	−0.0702 (3)	0.9941 (3)	0.0322 (7)
C8	0.2485 (5)	−0.0137 (4)	1.1072 (3)	0.0396 (8)
H8A	0.2515	−0.0724	1.1766	0.048*
C9	0.2326 (5)	0.1280 (4)	1.1146 (3)	0.0382 (8)
H9A	0.2249	0.1660	1.1896	0.046*
C10	0.2276 (5)	0.2173 (3)	1.0107 (3)	0.0312 (7)
C11	0.2530 (4)	0.0242 (3)	0.8937 (3)	0.0266 (6)
C12	0.2620 (4)	−0.0274 (3)	0.7747 (3)	0.0281 (7)
C13	0.2325 (6)	0.1281 (5)	0.4669 (3)	0.0461 (9)
H13A	0.1190	0.1850	0.4789	0.069*
H13B	0.2202	0.0809	0.3935	0.069*
H13C	0.3455	0.1867	0.4623	0.069*
C14	0.2121 (6)	0.3725 (4)	1.0190 (3)	0.0424 (9)
H14A	0.3391	0.4104	1.0304	0.064*
H14B	0.1298	0.3933	1.0858	0.064*
H14C	0.1574	0.4137	0.9462	0.064*
O1	0.4924 (4)	0.3945 (4)	0.7882 (3)	0.0622 (9)
O2	0.4560 (5)	0.3466 (4)	0.6052 (3)	0.0675 (9)
O3	0.9214 (4)	0.2696 (3)	0.6983 (3)	0.0646 (9)
O4	1.0687 (5)	0.4640 (4)	0.7095 (5)	0.0950 (15)
C15	0.5528 (5)	0.4017 (3)	0.6837 (3)	0.0331 (7)
C16	0.7380 (5)	0.4791 (4)	0.6502 (3)	0.0360 (8)
H16A	0.7421	0.4975	0.5638	0.043*
H16C	0.7359	0.5691	0.6869	0.043*
C17	0.9200 (5)	0.3999 (4)	0.6886 (3)	0.0343 (7)

	U11	U22	U33	U12	U13	U23
Co1	0.0319 (2)	0.0274 (2)	0.0321 (3)	−0.00231 (17)	−0.00176 (17)	0.00297 (17)
N1	0.0266 (13)	0.0290 (13)	0.0292 (14)	−0.0007 (11)	0.0004 (11)	−0.0026 (11)
N2	0.0265 (13)	0.0237 (12)	0.0289 (14)	−0.0015 (10)	−0.0022 (10)	−0.0008 (10)
C1	0.0240 (15)	0.045 (2)	0.0350 (18)	−0.0042 (14)	0.0005 (13)	−0.0083 (15)
C2	0.040 (2)	0.052 (2)	0.040 (2)	−0.0062 (17)	0.0002 (16)	−0.0192 (18)
C3	0.0363 (19)	0.0362 (19)	0.061 (3)	−0.0042 (16)	−0.0004 (17)	−0.0184 (18)
C4	0.0284 (16)	0.0271 (16)	0.049 (2)	−0.0028 (13)	0.0011 (15)	−0.0025 (15)
C5	0.0397 (19)	0.0227 (16)	0.068 (3)	−0.0011 (15)	−0.0021 (18)	0.0024 (16)
C6	0.0390 (19)	0.0301 (18)	0.053 (2)	−0.0029 (15)	−0.0025 (17)	0.0164 (16)
C7	0.0245 (15)	0.0318 (17)	0.0393 (19)	−0.0044 (13)	−0.0043 (13)	0.0089 (14)
C8	0.0374 (18)	0.047 (2)	0.0331 (19)	−0.0060 (16)	−0.0018 (15)	0.0127 (16)
C9	0.0413 (19)	0.050 (2)	0.0238 (17)	−0.0036 (16)	−0.0022 (14)	−0.0013 (15)
C10	0.0293 (16)	0.0340 (17)	0.0303 (17)	−0.0014 (14)	−0.0010 (13)	−0.0011 (13)
C11	0.0210 (14)	0.0272 (15)	0.0314 (17)	−0.0034 (12)	−0.0024 (12)	0.0022 (12)
C12	0.0223 (14)	0.0261 (15)	0.0360 (18)	−0.0014 (12)	0.0002 (12)	−0.0006 (13)
C13	0.046 (2)	0.064 (3)	0.0282 (19)	−0.0095 (19)	−0.0032 (16)	−0.0023 (17)
C14	0.052 (2)	0.0385 (19)	0.037 (2)	0.0000 (17)	0.0006 (17)	−0.0080 (16)
O1	0.0481 (16)	0.097 (3)	0.0412 (17)	−0.0195 (17)	0.0000 (13)	0.0045 (16)
O2	0.063 (2)	0.083 (2)	0.059 (2)	−0.0335 (18)	0.0073 (16)	−0.0249 (18)
O3	0.0481 (17)	0.0449 (17)	0.101 (3)	0.0117 (14)	−0.0200 (17)	−0.0033 (17)
O4	0.0404 (17)	0.059 (2)	0.183 (5)	−0.0152 (16)	−0.040 (2)	0.027 (2)
C15	0.0266 (15)	0.0300 (16)	0.042 (2)	0.0048 (13)	−0.0038 (14)	0.0032 (14)
C16	0.0349 (17)	0.0307 (17)	0.042 (2)	−0.0006 (14)	−0.0031 (15)	0.0068 (14)
C17	0.0327 (17)	0.0369 (18)	0.0327 (18)	0.0018 (15)	−0.0001 (14)	0.0021 (14)

Co1—O1	2.180 (3)	C7—C8	1.400 (5)
Co1—O2	2.145 (3)	C8—C9	1.361 (5)
Co1—O3i	2.229 (3)	C8—H8A	0.9300
Co1—O4i	2.126 (4)	C9—C10	1.399 (5)
Co1—N1	2.122 (3)	C9—H9A	0.9300
Co1—N2	2.103 (3)	C10—C14	1.489 (5)
Co1—C15	2.512 (4)	C11—C12	1.440 (5)
Co1—C17i	2.519 (3)	C13—H13A	0.9600
N1—C1	1.338 (4)	C13—H13B	0.9600
N1—C12	1.350 (4)	C13—H13C	0.9600
N2—C10	1.328 (4)	C14—H14A	0.9600
N2—C11	1.364 (4)	C14—H14B	0.9600
C1—C2	1.410 (5)	C14—H14C	0.9600
C1—C13	1.485 (5)	O1—C15	1.233 (4)
C2—C3	1.352 (6)	O2—C15	1.246 (5)
C2—H2A	0.9300	O3—C17	1.240 (4)
C3—C4	1.405 (5)	O3—Co1ii	2.229 (3)
C3—H3A	0.9300	O4—C17	1.226 (5)
C4—C12	1.411 (4)	O4—Co1ii	2.126 (4)
C4—C5	1.428 (5)	C15—C16	1.511 (5)
C5—C6	1.350 (6)	C16—C17	1.509 (5)
C5—H5A	0.9300	C16—H16A	0.9700
C6—C7	1.436 (5)	C16—H16C	0.9700
C6—H6A	0.9300	C17—Co1ii	2.519 (3)
C7—C11	1.398 (4)
N2—Co1—N1	79.24 (10)	C9—C8—H8A	120.3
N2—Co1—O4i	119.53 (16)	C7—C8—H8A	120.3
N1—Co1—O4i	140.97 (13)	C8—C9—C10	120.8 (3)
N2—Co1—O2	136.06 (13)	C8—C9—H9A	119.6
N1—Co1—O2	92.45 (12)	C10—C9—H9A	119.6
O4i—Co1—O2	93.90 (16)	N2—C10—C9	120.9 (3)
N2—Co1—O1	89.80 (11)	N2—C10—C14	118.4 (3)
N1—Co1—O1	123.50 (12)	C9—C10—C14	120.7 (3)
O4i—Co1—O1	92.30 (13)	N2—C11—C7	122.8 (3)
O2—Co1—O1	59.10 (12)	N2—C11—C12	117.3 (3)
N2—Co1—O3i	97.95 (12)	C7—C11—C12	119.9 (3)
N1—Co1—O3i	86.71 (11)	N1—C12—C4	123.0 (3)
O4i—Co1—O3i	58.47 (12)	N1—C12—C11	117.8 (3)
O2—Co1—O3i	124.82 (14)	C4—C12—C11	119.2 (3)
O1—Co1—O3i	149.76 (13)	C1—C13—H13A	109.5
C1—N1—C12	119.0 (3)	C1—C13—H13B	109.5
C1—N1—Co1	128.3 (2)	H13A—C13—H13B	109.5
C12—N1—Co1	112.6 (2)	C1—C13—H13C	109.5
C10—N2—C11	118.9 (3)	H13A—C13—H13C	109.5
C10—N2—Co1	128.1 (2)	H13B—C13—H13C	109.5
C11—N2—Co1	113.0 (2)	C10—C14—H14A	109.5
N1—C1—C2	120.9 (3)	C10—C14—H14B	109.5
N1—C1—C13	118.2 (3)	H14A—C14—H14B	109.5
C2—C1—C13	120.9 (3)	C10—C14—H14C	109.5
C3—C2—C1	120.4 (3)	H14A—C14—H14C	109.5
C3—C2—H2A	119.8	H14B—C14—H14C	109.5
C1—C2—H2A	119.8	C15—O1—Co1	90.4 (2)
C2—C3—C4	120.0 (3)	C15—O2—Co1	91.7 (2)
C2—C3—H3A	120.0	O1—C15—O2	118.8 (3)
C4—C3—H3A	120.0	O1—C15—C16	120.9 (3)
C3—C4—C12	116.7 (3)	O2—C15—C16	120.3 (3)
C3—C4—C5	123.9 (3)	O1—C15—Co1	60.2 (2)
C12—C4—C5	119.4 (3)	O2—C15—Co1	58.6 (2)
C6—C5—C4	121.2 (3)	C16—C15—Co1	178.2 (2)
C6—C5—H5A	119.4	C17—C16—C15	113.5 (3)
C4—C5—H5A	119.4	C17—C16—H16A	108.9
C5—C6—C7	120.8 (3)	C15—C16—H16A	108.9
C5—C6—H6A	119.6	C17—C16—H16C	108.9
C7—C6—H6A	119.6	C15—C16—H16C	108.9
C11—C7—C8	117.2 (3)	H16A—C16—H16C	107.7
C11—C7—C6	119.4 (3)	O4—C17—O3	119.4 (4)
C8—C7—C6	123.4 (3)	O4—C17—C16	120.1 (3)
C9—C8—C7	119.4 (3)	O3—C17—C16	120.5 (3)

Table 1

Selected bond lengths (Å)

Co1—O1	2.180 (3)
Co1—O2	2.145 (3)
Co1—O3i	2.229 (3)
Co1—O4i	2.126 (4)
Co1—N1	2.122 (3)
Co1—N2	2.103 (3)

Symmetry code: (i) .