Bis(2-methyl-benzoato-κO,O')(1,10'-phenanthroline-κN,N')copper(II).

In the title compound, [Cu(C(8)H(7)O(2))(2)(C(12)H(8)N(2))], the Cu(II) atom assumes a distorted octa-hedral coordination geometry, chelated by two N atoms from the 1,10'-phenanthroline ligand and four O atoms from two 2-methyl-benzoate anions. A significant Jahn-Teller distortion is observed with two axial Cu-O distances significantly longer than those in the equatorial CuO(2)N(2) plane. In the crystal, π-π stacking inter-actions, with centroid-centroid distances of 3.547 (3) or 3.728 (3) Å between the phenanthroline rings, form layers parallel to (011).

Related literature

For Jahn–Teller distortions in copper complexes, see: Yang & Vittal (2003 ▶); Su et al. (2005 ▶); Liu et al. (2010 ▶). For n class="Chemical">phenanthroline complexes, see: Wang et al. (1996 ▶); Wall et al. (1999 ▶); Naing et al. (1995 ▶). For related structures, see: Cano et al. (1997 ▶); Rodrigues et al. (1999 ▶) Xu & Xu (2004 ▶).

Experimental

Crystal data

[Cu(C8H7O2)2(n class="CellLine">C12H8N2)]

M = 514.02

Monoclinic,

a = 16.245 (3) Å

b = 10.136 (2) Å

c = 14.048 (3) Å

β = 99.15 (3)°

V = 2283.7 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.00 mm−1

T = 293 K

0.15 × 0.10 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.866, T max = 0.900

17441 measured reflections

4021 independent reflections

2509 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.150

S = 1.13

4021 reflections

319 parameters

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −1.04 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); 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/S1600536811018162/sj5144sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018162/sj5144Isup2.hkl

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

[Cu(C8H7O2)2(C12H8N2)]	F(000) = 1060
Mr = 514.02	Dx = 1.495 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 16.245 (3) Å	θ = 3.0–25.0°
b = 10.136 (2) Å	µ = 1.00 mm−1
c = 14.048 (3) Å	T = 293 K
β = 99.15 (3)°	Plate, blue
V = 2283.7 (8) Å3	0.15 × 0.10 × 0.10 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	4021 independent reflections
Radiation source: fine-focus sealed tube	2509 reflections with I > 2σ(I)
graphite	Rint = 0.063
ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −19→19
Tmin = 0.866, Tmax = 0.900	k = −12→12
17441 measured reflections	l = −16→16

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.150	w = 1/[σ2(Fo2) + (0.0447P)2 + 4.7675P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
4021 reflections	Δρmax = 0.74 e Å−3
319 parameters	Δρmin = −1.04 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0013 (5)

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
Cu	−0.33221 (4)	0.96309 (7)	−0.17022 (4)	0.0480 (2)
O1	−0.2996 (2)	1.1433 (4)	−0.1871 (3)	0.0703 (12)
O2	−0.2404 (2)	1.1033 (4)	−0.0382 (3)	0.0606 (10)
O3	−0.2325 (2)	0.8925 (4)	−0.2077 (3)	0.0635 (11)
O4	−0.3140 (2)	0.8977 (4)	−0.3495 (3)	0.0609 (10)
N1	−0.3735 (2)	0.7809 (4)	−0.1419 (3)	0.0450 (10)
N2	−0.4462 (2)	1.0137 (4)	−0.1442 (3)	0.0423 (9)
C1	−0.3348 (4)	0.6641 (6)	−0.1404 (4)	0.0584 (15)
H1	−0.2794	0.6613	−0.1496	0.070*
C2	−0.3756 (5)	0.5461 (6)	−0.1255 (4)	0.0698 (17)
H2	−0.3471	0.4665	−0.1251	0.084*
C3	−0.4558 (4)	0.5468 (6)	−0.1115 (4)	0.0607 (15)
H3	−0.4825	0.4678	−0.1024	0.073*
C4	−0.4990 (3)	0.6670 (5)	−0.1108 (3)	0.0478 (13)
C5	−0.5834 (3)	0.6805 (6)	−0.0943 (4)	0.0587 (15)
H5	−0.6141	0.6053	−0.0854	0.070*
C6	−0.6191 (3)	0.7998 (7)	−0.0914 (4)	0.0588 (15)
H6	−0.6734	0.8055	−0.0785	0.071*
C7	−0.5753 (3)	0.9185 (6)	−0.1076 (3)	0.0482 (13)
C8	−0.6084 (4)	1.0457 (6)	−0.1077 (4)	0.0606 (16)
H8	−0.6627	1.0579	−0.0962	0.073*
C9	−0.5615 (4)	1.1519 (6)	−0.1244 (4)	0.0623 (16)
H9	−0.5833	1.2366	−0.1235	0.075*
C10	−0.4806 (4)	1.1328 (5)	−0.1431 (4)	0.0565 (14)
H10	−0.4494	1.2061	−0.1552	0.068*
C11	−0.4933 (3)	0.9076 (5)	−0.1268 (3)	0.0395 (11)
C12	−0.4540 (3)	0.7812 (5)	−0.1262 (3)	0.0406 (11)
C13	−0.2490 (3)	1.1732 (5)	−0.1108 (4)	0.0476 (12)
C14	−0.2009 (3)	1.3008 (5)	−0.1152 (3)	0.0416 (11)
C15	−0.2043 (3)	1.3578 (5)	−0.2067 (4)	0.0509 (13)
H15	−0.2348	1.3161	−0.2599	0.061*
C16	−0.1637 (3)	1.4737 (6)	−0.2196 (4)	0.0619 (15)
H16	−0.1660	1.5092	−0.2811	0.074*
C17	−0.1197 (4)	1.5370 (6)	−0.1411 (5)	0.0667 (16)
H17	−0.0928	1.6163	−0.1490	0.080*
C18	−0.1157 (3)	1.4830 (6)	−0.0517 (5)	0.0604 (15)
H18	−0.0859	1.5272	0.0008	0.072*
C19	−0.1545 (3)	1.3636 (5)	−0.0356 (4)	0.0496 (13)
C20	−0.1458 (4)	1.3130 (7)	0.0666 (4)	0.080 (2)
H20A	−0.1327	1.2206	0.0676	0.120*
H20B	−0.1973	1.3262	0.0907	0.120*
H20C	−0.1019	1.3600	0.1063	0.120*
C21	−0.2458 (3)	0.8741 (5)	−0.2988 (4)	0.0494 (13)
C22	−0.1747 (3)	0.8162 (5)	−0.3429 (3)	0.0425 (11)
C23	−0.1959 (3)	0.7396 (5)	−0.4251 (3)	0.0531 (14)
H23	−0.2517	0.7325	−0.4527	0.064*
C24	−0.1363 (4)	0.6736 (6)	−0.4669 (4)	0.0615 (15)
H24	−0.1517	0.6217	−0.5214	0.074*
C25	−0.0538 (4)	0.6861 (6)	−0.4265 (4)	0.0612 (15)
H25	−0.0130	0.6410	−0.4528	0.073*
C26	−0.0319 (3)	0.7651 (6)	−0.3470 (4)	0.0555 (14)
H26	0.0243	0.7750	−0.3220	0.067*
C27	−0.0903 (3)	0.8306 (5)	−0.3028 (3)	0.0430 (12)
C28	−0.0598 (3)	0.9171 (6)	−0.2164 (4)	0.0629 (16)
H18A	−0.0909	0.9981	−0.2215	0.094*
H28B	−0.0017	0.9361	−0.2144	0.094*
H28C	−0.0676	0.8720	−0.1584	0.094*

	U11	U22	U33	U12	U13	U23
Cu	0.0409 (4)	0.0540 (4)	0.0480 (4)	−0.0059 (3)	0.0037 (3)	0.0006 (3)
O1	0.067 (2)	0.074 (3)	0.063 (2)	−0.024 (2)	−0.011 (2)	0.009 (2)
O2	0.075 (3)	0.049 (2)	0.057 (2)	−0.006 (2)	0.0108 (19)	0.0059 (19)
O3	0.049 (2)	0.094 (3)	0.048 (2)	−0.005 (2)	0.0121 (17)	0.000 (2)
O4	0.045 (2)	0.060 (2)	0.074 (3)	−0.0035 (18)	−0.0034 (18)	0.005 (2)
N1	0.040 (2)	0.053 (3)	0.041 (2)	0.010 (2)	0.0046 (17)	−0.003 (2)
N2	0.051 (2)	0.035 (2)	0.039 (2)	0.0028 (19)	0.0003 (18)	0.0003 (18)
C1	0.059 (3)	0.059 (4)	0.056 (3)	0.022 (3)	0.005 (3)	−0.002 (3)
C2	0.105 (5)	0.041 (3)	0.065 (4)	0.018 (4)	0.019 (4)	0.004 (3)
C3	0.091 (5)	0.044 (3)	0.050 (3)	−0.007 (3)	0.019 (3)	−0.001 (3)
C4	0.056 (3)	0.047 (3)	0.039 (3)	−0.009 (3)	0.001 (2)	−0.003 (2)
C5	0.054 (3)	0.075 (4)	0.047 (3)	−0.027 (3)	0.005 (3)	−0.001 (3)
C6	0.041 (3)	0.084 (5)	0.050 (3)	−0.007 (3)	0.004 (2)	−0.007 (3)
C7	0.040 (3)	0.062 (4)	0.039 (3)	0.006 (3)	−0.002 (2)	−0.005 (2)
C8	0.050 (3)	0.078 (4)	0.050 (3)	0.025 (3)	−0.002 (2)	−0.009 (3)
C9	0.070 (4)	0.059 (4)	0.053 (3)	0.031 (3)	−0.004 (3)	−0.009 (3)
C10	0.081 (4)	0.040 (3)	0.044 (3)	0.006 (3)	−0.004 (3)	0.003 (2)
C11	0.039 (3)	0.044 (3)	0.033 (2)	0.002 (2)	−0.003 (2)	−0.002 (2)
C12	0.041 (3)	0.042 (3)	0.035 (2)	0.005 (2)	−0.003 (2)	−0.005 (2)
C13	0.041 (3)	0.042 (3)	0.061 (3)	0.001 (2)	0.013 (3)	0.000 (3)
C14	0.036 (2)	0.039 (3)	0.050 (3)	0.000 (2)	0.007 (2)	−0.001 (2)
C15	0.043 (3)	0.054 (3)	0.056 (3)	−0.003 (2)	0.006 (2)	0.005 (3)
C16	0.057 (3)	0.061 (4)	0.071 (4)	0.003 (3)	0.021 (3)	0.021 (3)
C17	0.060 (4)	0.047 (3)	0.096 (5)	−0.006 (3)	0.023 (3)	0.000 (4)
C18	0.049 (3)	0.053 (4)	0.079 (4)	−0.007 (3)	0.008 (3)	−0.018 (3)
C19	0.046 (3)	0.053 (3)	0.051 (3)	−0.005 (3)	0.011 (2)	−0.006 (3)
C20	0.086 (5)	0.098 (5)	0.053 (4)	−0.023 (4)	0.002 (3)	−0.003 (3)
C21	0.039 (3)	0.053 (3)	0.057 (3)	−0.013 (2)	0.007 (2)	0.006 (3)
C22	0.044 (3)	0.042 (3)	0.043 (3)	−0.005 (2)	0.009 (2)	0.007 (2)
C23	0.058 (3)	0.056 (3)	0.043 (3)	−0.015 (3)	0.002 (2)	0.003 (3)
C24	0.088 (4)	0.050 (3)	0.049 (3)	−0.014 (3)	0.017 (3)	−0.007 (3)
C25	0.070 (4)	0.054 (4)	0.063 (4)	0.006 (3)	0.022 (3)	0.000 (3)
C26	0.051 (3)	0.062 (4)	0.053 (3)	−0.001 (3)	0.007 (3)	0.002 (3)
C27	0.042 (3)	0.041 (3)	0.045 (3)	−0.002 (2)	0.007 (2)	0.005 (2)
C28	0.048 (3)	0.079 (4)	0.061 (3)	−0.014 (3)	0.003 (3)	−0.013 (3)

Cu—O3	1.919 (4)	C11—C12	1.431 (6)
Cu—O1	1.927 (4)	C13—C14	1.518 (7)
Cu—N2	2.010 (4)	C14—C19	1.399 (7)
Cu—N1	2.025 (4)	C14—C15	1.402 (7)
O1—C13	1.279 (6)	C15—C16	1.374 (7)
O2—C13	1.230 (6)	C15—H15	0.9300
O3—C21	1.277 (6)	C16—C17	1.374 (8)
O4—C21	1.240 (6)	C16—H16	0.9300
N1—C1	1.339 (6)	C17—C18	1.362 (8)
N1—C12	1.361 (6)	C17—H17	0.9300
N2—C10	1.332 (6)	C18—C19	1.399 (7)
N2—C11	1.364 (6)	C18—H18	0.9300
C1—C2	1.399 (8)	C19—C20	1.510 (7)
C1—H1	0.9300	C20—H20A	0.9600
C2—C3	1.348 (8)	C20—H20B	0.9600
C2—H2	0.9300	C20—H20C	0.9600
C3—C4	1.406 (7)	C21—C22	1.515 (7)
C3—H3	0.9300	C22—C23	1.388 (7)
C4—C12	1.404 (7)	C22—C27	1.404 (6)
C4—C5	1.434 (7)	C23—C24	1.382 (8)
C5—C6	1.345 (8)	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.375 (8)
C6—C7	1.435 (8)	C24—H24	0.9300
C6—H6	0.9300	C25—C26	1.374 (7)
C7—C8	1.398 (7)	C25—H25	0.9300
C7—C11	1.404 (7)	C26—C27	1.383 (7)
C8—C9	1.360 (8)	C26—H26	0.9300
C8—H8	0.9300	C27—C28	1.516 (7)
C9—C10	1.393 (8)	C28—H18A	0.9600
C9—H9	0.9300	C28—H28B	0.9600
C10—H10	0.9300	C28—H28C	0.9600
O3—Cu—O1	93.39 (18)	O1—C13—C14	115.7 (5)
O3—Cu—N2	170.71 (16)	C19—C14—C15	118.9 (5)
O1—Cu—N2	93.45 (17)	C19—C14—C13	124.8 (4)
O3—Cu—N1	91.94 (17)	C15—C14—C13	116.3 (4)
O1—Cu—N1	173.96 (17)	C16—C15—C14	121.6 (5)
N2—Cu—N1	81.58 (15)	C16—C15—H15	119.2
C13—O1—Cu	105.9 (3)	C14—C15—H15	119.2
C21—O3—Cu	108.2 (3)	C15—C16—C17	119.5 (5)
C1—N1—C12	117.4 (5)	C15—C16—H16	120.3
C1—N1—Cu	129.8 (4)	C17—C16—H16	120.3
C12—N1—Cu	112.7 (3)	C18—C17—C16	119.7 (6)
C10—N2—C11	117.7 (4)	C18—C17—H17	120.2
C10—N2—Cu	129.3 (4)	C16—C17—H17	120.2
C11—N2—Cu	113.0 (3)	C17—C18—C19	122.7 (5)
N1—C1—C2	121.7 (5)	C17—C18—H18	118.7
N1—C1—H1	119.1	C19—C18—H18	118.7
C2—C1—H1	119.1	C14—C19—C18	117.6 (5)
C3—C2—C1	120.6 (6)	C14—C19—C20	124.2 (5)
C3—C2—H2	119.7	C18—C19—C20	118.1 (5)
C1—C2—H2	119.7	C19—C20—H20A	109.5
C2—C3—C4	120.0 (5)	C19—C20—H20B	109.5
C2—C3—H3	120.0	H20A—C20—H20B	109.5
C4—C3—H3	120.0	C19—C20—H20C	109.5
C12—C4—C3	116.2 (5)	H20A—C20—H20C	109.5
C12—C4—C5	118.7 (5)	H20B—C20—H20C	109.5
C3—C4—C5	125.1 (5)	O4—C21—O3	122.7 (5)
C6—C5—C4	121.3 (5)	O4—C21—C22	120.6 (5)
C6—C5—H5	119.4	O3—C21—C22	116.6 (4)
C4—C5—H5	119.4	C23—C22—C27	119.3 (5)
C5—C6—C7	121.4 (5)	C23—C22—C21	116.9 (4)
C5—C6—H6	119.3	C27—C22—C21	123.7 (4)
C7—C6—H6	119.3	C24—C23—C22	121.7 (5)
C8—C7—C11	116.7 (5)	C24—C23—H23	119.2
C8—C7—C6	124.9 (5)	C22—C23—H23	119.2
C11—C7—C6	118.4 (5)	C25—C24—C23	118.8 (5)
C9—C8—C7	120.3 (5)	C25—C24—H24	120.6
C9—C8—H8	119.9	C23—C24—H24	120.6
C7—C8—H8	119.9	C26—C25—C24	119.9 (5)
C8—C9—C10	119.6 (5)	C26—C25—H25	120.0
C8—C9—H9	120.2	C24—C25—H25	120.0
C10—C9—H9	120.2	C25—C26—C27	122.4 (5)
N2—C10—C9	122.5 (5)	C25—C26—H26	118.8
N2—C10—H10	118.7	C27—C26—H26	118.8
C9—C10—H10	118.7	C26—C27—C22	117.7 (5)
N2—C11—C7	123.2 (5)	C26—C27—C28	118.5 (4)
N2—C11—C12	116.4 (4)	C22—C27—C28	123.7 (4)
C7—C11—C12	120.3 (5)	C27—C28—H18A	109.5
N1—C12—C4	124.1 (4)	C27—C28—H28B	109.5
N1—C12—C11	116.1 (4)	H18A—C28—H28B	109.5
C4—C12—C11	119.8 (4)	C27—C28—H28C	109.5
O2—C13—O1	122.1 (5)	H18A—C28—H28C	109.5
O2—C13—C14	122.2 (5)	H28B—C28—H28C	109.5

Table 1

Selected bond lengths (Å)

Cu—O3	1.919 (4)
Cu—O1	1.927 (4)
Cu—N2	2.010 (4)
Cu—N1	2.025 (4)