Bis(3,4-dimethoxy-benzoato-κO,O')(1,10-phenanthroline-κN,N')copper(II).

The asymmetric unit of the title compound, [Cu(C(9)H(9)O(4))(2)(C(12)H(8)N(2))], contains one half-mol-ecule, the complete mol-ecule being generated by a twofold rotation axis. The Cu(II) atom exhibits a six-coordinated distorted octa-hedral geometry with two N atoms from the phenanthroline ligand [Cu-N 2.007 (2) Å] and four O atoms from two 3,4-dimethoxy-benzoate ligands [Cu-O 1.950 (1) and 2.524 (1) Å]. The difference in Cu-O bond distances indicates a strong Jahn-Teller effect. In the crystal, C-H⋯π inter-actions result in chains of mol-ecules along the c axis.

Related literature

For metal–1,10-phenanthroline complexes with unusual features, see: Ma et al. (2004 ▶); Bi et al. (2004 ▶).

Experimental

Crystal data

[Cu(C9H9O4)2(C12H8N2)]

M = 606.07

Monoclinic,

a = 12.1639 (10) Å

b = 11.4296 (9) Å

c = 19.7470 (16) Å

β = 104.027 (1)°

V = 2663.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.88 mm−1

T = 273 K

0.23 × 0.21 × 0.19 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.824, T max = 0.851

6857 measured reflections

2351 independent reflections

2136 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.086

S = 1.01

2351 reflections

187 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.38 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052234/ez2194sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052234/ez2194Isup2.hkl

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

[Cu(C9H9O4)2(C12H8N2)]	F(000) = 1252
Mr = 606.07	Dx = 1.511 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.1639 (10) Å	Cell parameters from 4483 reflections
b = 11.4296 (9) Å	θ = 2.5–28.3°
c = 19.7470 (16) Å	µ = 0.88 mm−1
β = 104.027 (1)°	T = 273 K
V = 2663.5 (4) Å3	Block, blue
Z = 4	0.23 × 0.21 × 0.19 mm

Bruker SMART APEX diffractometer	2351 independent reflections
Radiation source: fine-focus sealed tube	2136 reflections with I > 2σ(I)
graphite	Rint = 0.059
φ and ω scans	θmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→14
Tmin = 0.824, Tmax = 0.851	k = −10→13
6857 measured reflections	l = −23→22

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.045P)2 + 1.2527P] where P = (Fo2 + 2Fc2)/3
2351 reflections	(Δ/σ)max = 0.001
187 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.37 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
Cu1	0.0000	0.96118 (3)	0.2500	0.03588 (14)
O1	0.00052 (11)	0.87873 (12)	0.36863 (7)	0.0437 (3)
O2	0.10961 (12)	0.84452 (12)	0.29637 (7)	0.0445 (3)
O5	0.11674 (13)	0.56453 (14)	0.55593 (8)	0.0539 (4)
O6	0.27611 (14)	0.44980 (13)	0.52542 (9)	0.0592 (4)
N1	−0.10829 (13)	1.09400 (15)	0.21869 (8)	0.0389 (4)
C1	0.07772 (15)	0.82281 (16)	0.35206 (9)	0.0364 (4)
C2	0.13570 (15)	0.72454 (16)	0.39696 (9)	0.0341 (4)
C3	0.09898 (15)	0.69411 (16)	0.45613 (10)	0.0365 (4)
H3	0.0407	0.7364	0.4676	0.044*
C4	0.14771 (16)	0.60242 (17)	0.49769 (10)	0.0385 (4)
C5	0.23698 (17)	0.53957 (16)	0.48098 (11)	0.0406 (5)
C6	0.27502 (16)	0.57054 (18)	0.42332 (11)	0.0418 (5)
H6	0.3349	0.5300	0.4126	0.050*
C7	0.22402 (16)	0.66243 (17)	0.38092 (10)	0.0389 (4)
H7	0.2493	0.6823	0.3416	0.047*
C8	0.0266 (2)	0.6253 (2)	0.57448 (12)	0.0583 (6)
H8A	0.0494	0.7045	0.5868	0.087*
H8B	0.0079	0.5872	0.6135	0.087*
H8C	−0.0385	0.6255	0.5356	0.087*
C9	0.3730 (2)	0.3888 (3)	0.51835 (16)	0.0801 (9)
H9A	0.3578	0.3514	0.4735	0.120*
H9B	0.3926	0.3307	0.5544	0.120*
H9C	0.4349	0.4426	0.5223	0.120*
C19	−0.21817 (17)	1.0896 (2)	0.18725 (11)	0.0482 (5)
H19	−0.2525	1.0172	0.1756	0.058*
C20	−0.28296 (19)	1.1910 (2)	0.17132 (12)	0.0588 (6)
H20	−0.3597	1.1854	0.1497	0.071*
C21	−0.23515 (19)	1.2974 (2)	0.18712 (11)	0.0547 (6)
H21	−0.2793	1.3646	0.1774	0.066*
C22	−0.11811 (18)	1.30632 (18)	0.21845 (10)	0.0454 (5)
C23	−0.05979 (16)	1.20062 (17)	0.23347 (9)	0.0375 (4)
C29	−0.0562 (2)	1.41293 (19)	0.23526 (11)	0.0541 (6)
H29	−0.0942	1.4839	0.2257	0.065*

	U11	U22	U33	U12	U13	U23
Cu1	0.0365 (2)	0.0395 (2)	0.0311 (2)	0.000	0.00731 (14)	0.000
O1	0.0448 (7)	0.0459 (8)	0.0407 (7)	0.0081 (6)	0.0110 (6)	0.0047 (6)
O2	0.0497 (8)	0.0496 (8)	0.0357 (7)	0.0074 (6)	0.0134 (6)	0.0075 (6)
O5	0.0605 (9)	0.0624 (9)	0.0452 (8)	0.0236 (7)	0.0253 (7)	0.0197 (7)
O6	0.0618 (10)	0.0582 (10)	0.0624 (10)	0.0301 (8)	0.0244 (8)	0.0214 (8)
N1	0.0365 (8)	0.0467 (9)	0.0323 (8)	0.0016 (7)	0.0060 (7)	−0.0015 (7)
C1	0.0377 (9)	0.0363 (10)	0.0330 (9)	−0.0037 (8)	0.0044 (8)	−0.0019 (8)
C2	0.0369 (9)	0.0339 (9)	0.0304 (9)	−0.0024 (8)	0.0062 (7)	−0.0038 (8)
C3	0.0359 (9)	0.0377 (10)	0.0362 (10)	0.0059 (8)	0.0093 (8)	−0.0022 (8)
C4	0.0400 (10)	0.0423 (11)	0.0345 (10)	0.0049 (8)	0.0115 (8)	0.0023 (8)
C5	0.0415 (10)	0.0381 (11)	0.0410 (11)	0.0074 (8)	0.0077 (9)	0.0009 (8)
C6	0.0391 (10)	0.0430 (10)	0.0449 (11)	0.0061 (8)	0.0133 (9)	−0.0075 (9)
C7	0.0426 (10)	0.0421 (10)	0.0336 (9)	−0.0013 (8)	0.0125 (8)	−0.0040 (8)
C8	0.0647 (14)	0.0700 (15)	0.0497 (12)	0.0195 (12)	0.0321 (11)	0.0105 (11)
C9	0.0833 (19)	0.0836 (19)	0.0792 (18)	0.0514 (16)	0.0313 (15)	0.0234 (15)
C19	0.0376 (10)	0.0640 (13)	0.0404 (11)	0.0020 (10)	0.0042 (9)	−0.0029 (10)
C20	0.0405 (11)	0.0834 (18)	0.0493 (13)	0.0151 (12)	0.0046 (10)	0.0050 (12)
C21	0.0580 (13)	0.0639 (15)	0.0431 (12)	0.0226 (12)	0.0139 (10)	0.0087 (11)
C22	0.0599 (12)	0.0508 (12)	0.0290 (9)	0.0124 (10)	0.0173 (9)	0.0053 (9)
C23	0.0435 (10)	0.0451 (11)	0.0255 (9)	0.0019 (8)	0.0116 (8)	0.0001 (8)
C29	0.0834 (15)	0.0426 (11)	0.0415 (12)	0.0092 (11)	0.0251 (11)	0.0036 (10)

Cu1—O2i	1.950 (1)	C6—C7	1.392 (3)
Cu1—O2	1.950 (1)	C6—H6	0.9300
Cu1—N1i	2.007 (2)	C7—H7	0.9300
Cu1—N1	2.007 (2)	C8—H8A	0.9600
Cu1—O1	2.524 (1)	C8—H8B	0.9600
O1—C1	1.244 (2)	C8—H8C	0.9600
O2—C1	1.276 (2)	C9—H9A	0.9600
O5—C4	1.365 (2)	C9—H9B	0.9600
O5—C8	1.419 (2)	C9—H9C	0.9600
O6—C5	1.359 (2)	C19—C20	1.394 (3)
O6—C9	1.406 (3)	C19—H19	0.9300
N1—C19	1.331 (2)	C20—C21	1.351 (3)
N1—C23	1.355 (2)	C20—H20	0.9300
C1—C2	1.497 (3)	C21—C22	1.412 (3)
C2—C7	1.387 (3)	C21—H21	0.9300
C2—C3	1.392 (3)	C22—C23	1.396 (3)
C3—C4	1.374 (3)	C22—C29	1.429 (3)
C3—H3	0.9300	C23—C23i	1.443 (4)
C4—C5	1.406 (3)	C29—C29i	1.350 (5)
C5—C6	1.375 (3)	C29—H29	0.9300
O2i—Cu1—O2	93.72 (9)	C7—C6—H6	119.9
O2i—Cu1—N1i	170.07 (6)	C2—C7—C6	120.39 (18)
O2—Cu1—N1i	92.84 (6)	C2—C7—H7	119.8
O2i—Cu1—N1	92.84 (6)	C6—C7—H7	119.8
O2—Cu1—N1	170.07 (6)	O5—C8—H8A	109.5
N1i—Cu1—N1	81.69 (9)	O5—C8—H8B	109.5
O2i—Cu1—O1	91.61 (5)	H8A—C8—H8B	109.5
O2—Cu1—O1	57.40 (5)	O5—C8—H8C	109.5
N1i—Cu1—O1	98.20 (5)	H8A—C8—H8C	109.5
N1—Cu1—O1	114.98 (5)	H8B—C8—H8C	109.5
C1—O1—Cu1	77.28 (11)	O6—C9—H9A	109.5
C1—O2—Cu1	102.80 (12)	O6—C9—H9B	109.5
C4—O5—C8	116.78 (15)	H9A—C9—H9B	109.5
C5—O6—C9	118.78 (19)	O6—C9—H9C	109.5
C19—N1—C23	118.06 (18)	H9A—C9—H9C	109.5
C19—N1—Cu1	128.66 (15)	H9B—C9—H9C	109.5
C23—N1—Cu1	113.28 (12)	N1—C19—C20	121.5 (2)
O1—C1—O2	122.24 (17)	N1—C19—H19	119.3
O1—C1—C2	120.47 (17)	C20—C19—H19	119.3
O2—C1—C2	117.28 (16)	C21—C20—C19	120.5 (2)
C7—C2—C3	119.18 (17)	C21—C20—H20	119.7
C7—C2—C1	121.90 (17)	C19—C20—H20	119.7
C3—C2—C1	118.91 (16)	C20—C21—C22	119.9 (2)
C4—C3—C2	120.81 (17)	C20—C21—H21	120.1
C4—C3—H3	119.6	C22—C21—H21	120.1
C2—C3—H3	119.6	C23—C22—C21	115.9 (2)
O5—C4—C3	125.33 (17)	C23—C22—C29	118.47 (19)
O5—C4—C5	114.98 (16)	C21—C22—C29	125.62 (19)
C3—C4—C5	119.69 (18)	N1—C23—C22	124.09 (17)
O6—C5—C6	126.41 (18)	N1—C23—C23i	115.86 (10)
O6—C5—C4	113.81 (18)	C22—C23—C23i	120.05 (12)
C6—C5—C4	119.77 (18)	C29i—C29—C22	121.46 (12)
C5—C6—C7	120.13 (18)	C29i—C29—H29	119.3
C5—C6—H6	119.9	C22—C29—H29	119.3

C1 is the centroid of the C22,C23,C29,C22',C23',C29' ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···Cg1	0.96	2.98	3.642 (3)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯Cg1	0.96	2.98	3.642 (3)	127

C1 is the centroid of the C22,C23,C29,C22′,C23′,C29′ ring.