Bis(benzoato-κO,O')(2,9-dimethyl-1,10-phenanthroline-κN,N')cobalt(II).

In the title compound, [Co(C(7)H(5)O(2))(2)(C(14)H(12)N(2))], the Co(II) ion is located on a twofold rotation axis and is chelated by a 2,9-dimethyl-1,10-phenanthroline (dmphen) ligand and two benzoate anions in a distorted octa-hedral geometry. The crystal packing is stabilized by π-π inter-actions between parallel dmphen ligands of neighbouring mol-ecules, with a face-to-face distance of 3.411 (2) Å.

Related literature

For background information on cobalt coordination chemistry, see: Wang et al. (1996 ▶); Wall et al. (1999 ▶); Naing et al. (1995 ▶). For related structures, see: Wu et al. (2003 ▶); Su et al. (2005 ▶); Ding et al. (2006 ▶); Ren et al. (2007 ▶); Zhong et al. (2006 ▶); Li et al. (2007 ▶).

Experimental

Crystal data

[Co(C7H5O2)2(C14H12N2)]

M = 509.41

Monoclinic,

a = 17.632 (3) Å

b = 14.410 (2) Å

c = 9.5282 (15) Å

β = 90.796 (2)°

V = 2420.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.75 mm−1

T = 293 (2) K

0.30 × 0.22 × 0.22 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.805, T max = 0.856

8882 measured reflections

2253 independent reflections

1840 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.111

S = 1.06

2253 reflections

180 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.37 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068080/xu2376sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068080/xu2376Isup2.hkl

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

[Co(C7H5O2)2(C14H12N2)]	F000 = 1052
Mr = 509.41	Dx = 1.398 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2433 reflections
a = 17.632 (3) Å	θ = 2.3–22.5º
b = 14.410 (2) Å	µ = 0.75 mm−1
c = 9.5282 (15) Å	T = 293 (2) K
β = 90.796 (2)º	Block, brown
V = 2420.6 (7) Å3	0.30 × 0.22 × 0.22 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2253 independent reflections
Radiation source: fine-focus sealed tube	1840 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
T = 293(2) K	θmax = 25.5º
φ and ω scans	θmin = 2.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −21→21
Tmin = 0.805, Tmax = 0.856	k = −17→17
8882 measured reflections	l = −11→11

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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0507P)2 + 2.0726P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2253 reflections	Δρmax = 0.49 e Å−3
180 parameters	Δρmin = −0.37 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	Occ. (<1)
Co1	0.5000	0.76395 (3)	0.7500	0.0542 (2)
C1	0.63842 (19)	0.7820 (2)	0.9976 (4)	0.0839 (10)
H1A	0.5975	0.7472	1.0373	0.126*
H1B	0.6776	0.7906	1.0673	0.126*
H1C	0.6585	0.7488	0.9191	0.126*
C2	0.60968 (14)	0.8746 (2)	0.9496 (3)	0.0593 (7)
C3	0.63991 (16)	0.9577 (2)	1.0038 (3)	0.0678 (8)
H3	0.6782	0.9552	1.0719	0.081*
C4	0.61443 (17)	1.0410 (2)	0.9589 (3)	0.0651 (8)
H4	0.6345	1.0953	0.9966	0.078*
C5	0.55731 (15)	1.04513 (18)	0.8547 (3)	0.0560 (6)
C6	0.52910 (13)	0.96006 (17)	0.8040 (2)	0.0471 (6)
C7	0.52756 (18)	1.1299 (2)	0.8001 (3)	0.0693 (8)
H7	0.5463	1.1861	0.8338	0.083*
C8	0.57021 (17)	0.68233 (18)	0.5604 (3)	0.0602 (7)
C9	0.6070 (2)	0.6373 (2)	0.4415 (3)	0.054 (4)	0.452 (14)
C10	0.68276 (16)	0.6552 (3)	0.4177 (4)	0.066 (3)	0.452 (14)
H10	0.7095	0.6954	0.4766	0.079*	0.452 (14)
C11	0.71880 (15)	0.6135 (3)	0.3065 (4)	0.078 (6)	0.452 (14)
H11	0.7698	0.6255	0.2905	0.094*	0.452 (14)
C12	0.6791 (3)	0.5537 (4)	0.2190 (5)	0.096 (4)	0.452 (14)
H12	0.7034	0.5256	0.1441	0.115*	0.452 (14)
C13	0.6034 (3)	0.5358 (6)	0.2427 (7)	0.111 (4)	0.452 (14)
H13	0.5767	0.4956	0.1838	0.133*	0.452 (14)
C14	0.5674 (3)	0.5776 (6)	0.3540 (6)	0.084 (3)	0.452 (14)
H14	0.5164	0.5655	0.3700	0.100*	0.452 (14)
C9'	0.6177 (2)	0.63122 (19)	0.4495 (3)	0.056 (3)	0.548 (14)
C10'	0.68099 (17)	0.6701 (2)	0.3936 (5)	0.064 (3)	0.548 (14)
H10'	0.6970	0.7284	0.4236	0.077*	0.548 (14)
C11'	0.72124 (15)	0.6236 (2)	0.2934 (4)	0.083 (5)	0.548 (14)
H11'	0.7643	0.6505	0.2553	0.100*	0.548 (14)
C12'	0.6981 (3)	0.5377 (2)	0.2495 (5)	0.084 (3)	0.548 (14)
H12'	0.7257	0.5059	0.1823	0.101*	0.548 (14)
C13'	0.6347 (5)	0.4987 (3)	0.3043 (9)	0.090 (3)	0.548 (14)
H13'	0.6185	0.4407	0.2734	0.108*	0.548 (14)
C14'	0.5949 (4)	0.5449 (3)	0.4048 (7)	0.072 (2)	0.548 (14)
H14'	0.5521	0.5177	0.4431	0.087*	0.548 (14)
N1	0.55395 (11)	0.87653 (14)	0.8526 (2)	0.0496 (5)
O1	0.60107 (14)	0.74637 (15)	0.6274 (3)	0.0847 (5)
O2	0.50361 (13)	0.65984 (16)	0.5879 (2)	0.0847 (5)

	U11	U22	U33	U12	U13	U23
Co1	0.0625 (3)	0.0494 (3)	0.0509 (3)	0.000	0.0041 (2)	0.000
C1	0.076 (2)	0.098 (3)	0.077 (2)	0.0292 (18)	−0.0178 (17)	0.0002 (18)
C2	0.0486 (14)	0.0791 (19)	0.0502 (15)	0.0093 (13)	0.0026 (11)	−0.0044 (13)
C3	0.0521 (16)	0.098 (2)	0.0530 (16)	−0.0035 (15)	−0.0033 (12)	−0.0160 (15)
C4	0.0679 (18)	0.075 (2)	0.0522 (16)	−0.0159 (15)	0.0081 (13)	−0.0161 (14)
C5	0.0638 (16)	0.0613 (16)	0.0433 (13)	−0.0074 (12)	0.0138 (12)	−0.0070 (11)
C6	0.0506 (14)	0.0547 (14)	0.0363 (12)	0.0007 (11)	0.0101 (10)	−0.0017 (10)
C7	0.099 (2)	0.0540 (16)	0.0549 (17)	−0.0078 (14)	0.0167 (14)	−0.0058 (12)
C8	0.0749 (18)	0.0479 (15)	0.0579 (16)	−0.0033 (13)	0.0010 (14)	0.0031 (12)
C9	0.059 (5)	0.049 (7)	0.055 (7)	0.002 (5)	0.015 (5)	0.007 (5)
C10	0.066 (8)	0.075 (6)	0.056 (5)	−0.008 (5)	−0.008 (5)	−0.001 (4)
C11	0.051 (9)	0.105 (12)	0.079 (10)	0.001 (8)	0.001 (7)	0.006 (10)
C12	0.096 (7)	0.120 (9)	0.072 (6)	0.012 (6)	0.010 (5)	−0.035 (5)
C13	0.103 (7)	0.129 (9)	0.103 (7)	−0.024 (7)	0.017 (6)	−0.059 (7)
C14	0.074 (5)	0.089 (6)	0.088 (6)	−0.014 (5)	0.013 (5)	−0.034 (5)
C9'	0.062 (5)	0.058 (6)	0.047 (6)	−0.003 (4)	−0.004 (4)	−0.006 (4)
C10'	0.062 (6)	0.059 (4)	0.073 (4)	0.000 (4)	0.004 (4)	0.009 (4)
C11'	0.071 (9)	0.099 (9)	0.080 (9)	0.007 (7)	0.028 (7)	0.012 (8)
C12'	0.076 (4)	0.110 (6)	0.067 (4)	0.015 (5)	0.016 (4)	−0.010 (5)
C13'	0.097 (6)	0.086 (5)	0.086 (5)	−0.018 (4)	0.010 (4)	−0.039 (4)
C14'	0.068 (4)	0.073 (4)	0.077 (4)	−0.020 (3)	0.016 (4)	−0.014 (3)
N1	0.0488 (12)	0.0589 (13)	0.0412 (11)	0.0050 (9)	0.0029 (9)	−0.0033 (9)
O1	0.0876 (11)	0.0800 (11)	0.0870 (11)	−0.0088 (8)	0.0221 (9)	−0.0209 (8)
O2	0.0876 (11)	0.0800 (11)	0.0870 (11)	−0.0088 (8)	0.0221 (9)	−0.0209 (8)

Co1—N1	2.114 (2)	C8—C9	1.465 (4)
Co1—N1i	2.114 (2)	C8—C9'	1.544 (4)
Co1—O1	2.159 (2)	C9—C10	1.3816 (16)
Co1—O1i	2.159 (2)	C9—C14	1.3816 (16)
Co1—O2i	2.154 (2)	C10—C11	1.3815 (16)
Co1—O2	2.154 (2)	C10—H10	0.9300
Co1—C8i	2.498 (3)	C11—C12	1.3816 (16)
C1—C2	1.497 (4)	C11—H11	0.9300
C1—H1A	0.9600	C12—C13	1.3816 (16)
C1—H1B	0.9600	C12—H12	0.9300
C1—H1C	0.9600	C13—C14	1.3816 (16)
C2—N1	1.339 (3)	C13—H13	0.9300
C2—C3	1.406 (4)	C14—H14	0.9300
C3—C4	1.349 (4)	C9'—C10'	1.3643 (16)
C3—H3	0.9300	C9'—C14'	1.3726 (16)
C4—C5	1.406 (4)	C10'—C11'	1.3726 (16)
C4—H4	0.9300	C10'—H10'	0.9300
C5—C6	1.406 (3)	C11'—C12'	1.3660 (16)
C5—C7	1.425 (4)	C11'—H11'	0.9300
C6—N1	1.360 (3)	C12'—C13'	1.3619 (15)
C6—C6i	1.444 (5)	C12'—H12'	0.9300
C7—C7i	1.353 (6)	C13'—C14'	1.3685 (16)
C7—H7	0.9300	C13'—H13'	0.9300
C8—O1	1.243 (3)	C14'—H14'	0.9300
C8—O2	1.249 (3)
N1—Co1—N1i	79.73 (11)	O1—C8—C9	122.0 (3)
N1—Co1—O2i	102.73 (9)	O2—C8—C9	118.4 (3)
N1i—Co1—O2i	148.05 (8)	O1—C8—C9'	117.9 (3)
N1—Co1—O2	148.05 (8)	O2—C8—C9'	122.7 (3)
N1i—Co1—O2	102.73 (9)	C10—C9—C14	120.0
O2i—Co1—O2	91.74 (13)	C10—C9—C8	118.9 (2)
N1—Co1—O1	88.33 (8)	C14—C9—C8	121.1 (2)
N1i—Co1—O1	102.08 (9)	C11—C10—C9	120.0
O2i—Co1—O1	109.81 (9)	C11—C10—H10	120.0
O2—Co1—O1	59.85 (8)	C9—C10—H10	120.0
N1—Co1—O1i	102.08 (9)	C10—C11—C12	120.0
N1i—Co1—O1i	88.33 (8)	C10—C11—H11	120.0
O2i—Co1—O1i	59.85 (8)	C12—C11—H11	120.0
O2—Co1—O1i	109.81 (9)	C11—C12—C13	120.0
O1—Co1—O1i	166.53 (12)	C11—C12—H12	120.0
N1—Co1—C8i	104.54 (8)	C13—C12—H12	120.0
N1i—Co1—C8i	118.14 (8)	C12—C13—C14	120.0
O2i—Co1—C8i	30.01 (8)	C12—C13—H13	120.0
O2—Co1—C8i	102.14 (9)	C14—C13—H13	120.0
O1—Co1—C8i	139.20 (10)	C9—C14—C13	120.0
O1i—Co1—C8i	29.84 (8)	C9—C14—H14	120.0
C2—C1—H1A	109.5	C13—C14—H14	120.0
C2—C1—H1B	109.5	C10'—C9'—C14'	119.2
H1A—C1—H1B	109.5	C10'—C9'—C8	121.72 (19)
C2—C1—H1C	109.5	C14'—C9'—C8	119.06 (19)
H1A—C1—H1C	109.5	C9'—C10'—C11'	120.3
H1B—C1—H1C	109.5	C9'—C10'—H10'	119.8
N1—C2—C3	120.4 (3)	C11'—C10'—H10'	119.8
N1—C2—C1	118.1 (3)	C12'—C11'—C10'	120.0
C3—C2—C1	121.4 (3)	C12'—C11'—H11'	120.0
C4—C3—C2	121.2 (3)	C10'—C11'—H11'	120.0
C4—C3—H3	119.4	C13'—C12'—C11'	120.0
C2—C3—H3	119.4	C13'—C12'—H12'	120.0
C3—C4—C5	119.6 (3)	C11'—C12'—H12'	120.0
C3—C4—H4	120.2	C12'—C13'—C14'	119.9
C5—C4—H4	120.2	C12'—C13'—H13'	120.0
C4—C5—C6	116.9 (3)	C14'—C13'—H13'	120.0
C4—C5—C7	123.4 (3)	C13'—C14'—C9'	120.5
C6—C5—C7	119.7 (2)	C13'—C14'—H14'	119.8
N1—C6—C5	123.0 (2)	C9'—C14'—H14'	119.8
N1—C6—C6i	117.74 (13)	C2—N1—C6	118.9 (2)
C5—C6—C6i	119.30 (15)	C2—N1—Co1	128.61 (18)
C7i—C7—C5	120.99 (16)	C6—N1—Co1	112.39 (15)
C7i—C7—H7	119.5	C8—O1—Co1	90.36 (19)
C5—C7—H7	119.5	C8—O2—Co1	90.41 (17)
O1—C8—O2	119.4 (3)
N1—C2—C3—C4	−0.8 (4)	C3—C2—N1—C6	2.3 (4)
C1—C2—C3—C4	179.2 (3)	C1—C2—N1—C6	−177.6 (2)
C2—C3—C4—C5	−0.8 (4)	C3—C2—N1—Co1	178.41 (18)
C3—C4—C5—C6	0.8 (4)	C1—C2—N1—Co1	−1.5 (4)
C3—C4—C5—C7	−179.4 (3)	C5—C6—N1—C2	−2.4 (3)
C4—C5—C6—N1	0.9 (4)	C6i—C6—N1—C2	177.8 (2)
C7—C5—C6—N1	−179.0 (2)	C5—C6—N1—Co1	−179.10 (18)
C4—C5—C6—C6i	−179.4 (2)	C6i—C6—N1—Co1	1.2 (3)
C7—C5—C6—C6i	0.8 (4)	N1i—Co1—N1—C2	−176.7 (3)
C4—C5—C7—C7i	−179.9 (3)	O2i—Co1—N1—C2	35.9 (2)
C6—C5—C7—C7i	0.0 (5)	O2—Co1—N1—C2	−79.0 (3)
O1—C8—C9—C10	11.2 (5)	O1—Co1—N1—C2	−74.1 (2)
O2—C8—C9—C10	−174.2 (4)	O1i—Co1—N1—C2	97.3 (2)
C9'—C8—C9—C10	−49.13 (12)	C8i—Co1—N1—C2	66.7 (2)
O1—C8—C9—C14	−169.0 (5)	N1i—Co1—N1—C6	−0.41 (11)
O2—C8—C9—C14	5.7 (5)	O2i—Co1—N1—C6	−147.88 (16)
C9'—C8—C9—C14	130.70 (19)	O2—Co1—N1—C6	97.2 (2)
C14—C9—C10—C11	0.0	O1—Co1—N1—C6	102.19 (17)
C8—C9—C10—C11	179.8 (3)	O1i—Co1—N1—C6	−86.45 (17)
C9—C10—C11—C12	0.0	C8i—Co1—N1—C6	−117.03 (16)
C10—C11—C12—C13	0.0	O2—C8—O1—Co1	0.7 (3)
C11—C12—C13—C14	0.0	C9—C8—O1—Co1	175.3 (3)
C10—C9—C14—C13	0.0	C9'—C8—O1—Co1	−177.0 (2)
C8—C9—C14—C13	−179.8 (3)	N1—Co1—O1—C8	−177.35 (18)
C12—C13—C14—C9	0.0	N1i—Co1—O1—C8	−98.22 (18)
O1—C8—C9'—C10'	−20.3 (5)	O2i—Co1—O1—C8	79.71 (19)
O2—C8—C9'—C10'	162.1 (4)	O2—Co1—O1—C8	−0.39 (17)
C9—C8—C9'—C10'	103.27 (16)	O1i—Co1—O1—C8	41.69 (17)
O1—C8—C9'—C14'	160.6 (4)	C8i—Co1—O1—C8	72.1 (3)
O2—C8—C9'—C14'	−17.0 (5)	O1—C8—O2—Co1	−0.7 (3)
C9—C8—C9'—C14'	−75.85 (18)	C9—C8—O2—Co1	−175.5 (3)
C14'—C9'—C10'—C11'	0.3	C9'—C8—O2—Co1	176.9 (3)
C8—C9'—C10'—C11'	−178.9 (3)	N1—Co1—O2—C8	6.1 (3)
C9'—C10'—C11'—C12'	−0.3	N1i—Co1—O2—C8	97.09 (18)
C10'—C11'—C12'—C13'	0.6	O2i—Co1—O2—C8	−111.61 (19)
C11'—C12'—C13'—C14'	−1.0	O1—Co1—O2—C8	0.38 (17)
C12'—C13'—C14'—C9'	1.0	O1i—Co1—O2—C8	−170.06 (17)
C10'—C9'—C14'—C13'	−0.6	C8i—Co1—O2—C8	−140.01 (16)
C8—C9'—C14'—C13'	178.5 (3)

Table 1

Selected bond lengths (Å)

Co1—N1	2.114 (2)
Co1—O1	2.159 (2)
Co1—O2	2.154 (2)