(Croconato-κO,O')bis-(1,10-phenanthroline-κN,N')zinc(II).

In the title compound, [Zn(C(5)O(5))(C(12)H(8)N(2))(2)], the Zn atom is in a slightly distorted octa-hedral environment. The mol-ecule lies across a twofold rotation axis, around which two 1,10-phenanthroline ligands are arranged. There are short contacts between the 1,10-phenanthroline groups and the O atoms of the croconate ligand, which probably stabilize the crystal structure via weak C-H⋯O interactions.

Related literature

For related literature, see: Braga et al. (2002 ▶); Carranza et al. (2004 ▶); Castro et al. (1992 ▶, 2002 ▶); Chen et al. (2005 ▶, 2007 ▶, 2008 ▶); Faus et al. (1994 ▶); Maji et al. (2003 ▶); Seitz & Imming (1992 ▶); Sletten et al. (1998 ▶); Wang et al. (2002 ▶).

Experimental

Crystal data

[Zn(C5O5)(C12H8N2)2]

M = 565.83

Orthorhombic,

a = 12.2605 (4) Å

b = 11.0133 (3) Å

c = 17.2745 (5) Å

V = 2332.55 (12) Å3

Z = 4

Mo Kα radiation

μ = 1.11 mm−1

T = 293 (2) K

0.28 × 0.23 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (APEX2; Bruker, 2005 ▶) T min = 0.743, T max = 0.782 (expected range = 0.805–0.847)

9769 measured reflections

2627 independent reflections

2164 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.096

S = 1.28

2627 reflections

179 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033709/sg2254sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033709/sg2254Isup2.hkl

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

[Zn(C5O5)(C12H8N2)2]	F000 = 1152
Mr = 565.83	Dx = 1.611 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 3967 reflections
a = 12.2605 (4) Å	θ = 2.8–27.5º
b = 11.0133 (3) Å	µ = 1.11 mm−1
c = 17.2745 (5) Å	T = 293 (2) K
V = 2332.55 (12) Å3	Prism, yellow
Z = 4	0.28 × 0.23 × 0.15 mm

Bruker APEXII CCD area-detector diffractometer	2627 independent reflections
Radiation source: fine-focus sealed tube	2164 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.019
Detector resolution: 10.0 pixels mm-1	θmax = 27.6º
T = 295(2) K	θmin = 2.4º
φ and ω scans	h = −15→14
Absorption correction: multi-scan(APEX2; Bruker, 2005)	k = −14→13
Tmin = 0.743, Tmax = 0.782	l = −21→21
9769 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.029	w = 1/[σ2(Fo2) + (0.0414P)2 + 0.6435P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096	(Δ/σ)max < 0.001
S = 1.28	Δρmax = 0.29 e Å−3
2627 reflections	Δρmin = −0.32 e Å−3
179 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0037 (5)
Secondary atom site location: difference Fourier map

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	1.14583 (16)	−0.08987 (18)	0.66696 (12)	0.0370 (4)
H1	1.1977	−0.0725	0.7047	0.044*
C2	1.17077 (19)	−0.1768 (2)	0.61125 (13)	0.0442 (5)
H2	1.2374	−0.2171	0.6123	0.053*
C3	1.09642 (18)	−0.20164 (18)	0.55543 (12)	0.0411 (5)
H3	1.1121	−0.2598	0.5180	0.049*
C4	0.99594 (16)	−0.14043 (18)	0.55356 (12)	0.0346 (4)
C5	0.97663 (15)	−0.05585 (16)	0.61341 (10)	0.0284 (4)
C6	0.91524 (18)	−0.15647 (19)	0.49514 (12)	0.0406 (5)
H6	0.9282	−0.2110	0.4551	0.049*
C7	0.82034 (19)	−0.09419 (19)	0.49667 (13)	0.0434 (5)
H7	0.7700	−0.1051	0.4570	0.052*
C8	0.79598 (16)	−0.01181 (19)	0.55831 (11)	0.0371 (4)
C9	0.87469 (15)	0.00774 (16)	0.61615 (11)	0.0305 (4)
C10	0.69824 (18)	0.0534 (2)	0.56380 (14)	0.0503 (6)
H10	0.6443	0.0438	0.5264	0.060*
C11	0.68264 (19)	0.1309 (2)	0.62399 (15)	0.0535 (6)
H11	0.6177	0.1740	0.6281	0.064*
C12	0.76426 (18)	0.1457 (2)	0.67964 (13)	0.0460 (5)
H12	0.7522	0.1985	0.7208	0.055*
C13	0.96697 (16)	0.35065 (18)	0.78378 (11)	0.0334 (4)
C14	0.94811 (17)	0.47521 (18)	0.80990 (13)	0.0409 (5)
C15	1.0000	0.5549 (3)	0.7500	0.0419 (7)
N1	1.05186 (12)	−0.03074 (13)	0.66885 (9)	0.0290 (3)
N2	0.85892 (13)	0.08653 (15)	0.67547 (9)	0.0352 (4)
O1	0.93325 (12)	0.25245 (13)	0.81491 (8)	0.0415 (3)
O2	0.89952 (16)	0.50881 (16)	0.86832 (11)	0.0659 (5)
O3	1.0000	0.6664 (2)	0.7500	0.0560 (7)
Zn1	1.0000	0.10546 (3)	0.7500	0.03197 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0350 (10)	0.0405 (11)	0.0355 (11)	0.0036 (8)	−0.0035 (8)	0.0000 (8)
C2	0.0441 (11)	0.0421 (11)	0.0465 (13)	0.0118 (9)	0.0055 (10)	−0.0014 (9)
C3	0.0551 (13)	0.0326 (10)	0.0356 (11)	0.0030 (9)	0.0093 (9)	−0.0061 (9)
C4	0.0457 (11)	0.0278 (8)	0.0302 (10)	−0.0086 (8)	0.0057 (8)	−0.0008 (8)
C5	0.0348 (9)	0.0270 (9)	0.0235 (9)	−0.0044 (7)	−0.0003 (7)	0.0029 (7)
C6	0.0579 (13)	0.0387 (11)	0.0253 (10)	−0.0166 (10)	−0.0015 (9)	−0.0029 (8)
C7	0.0504 (12)	0.0458 (12)	0.0340 (12)	−0.0204 (10)	−0.0078 (9)	0.0041 (9)
C8	0.0347 (9)	0.0427 (11)	0.0340 (11)	−0.0090 (8)	−0.0040 (8)	0.0107 (8)
C9	0.0325 (9)	0.0317 (9)	0.0275 (10)	−0.0034 (7)	0.0032 (7)	0.0062 (7)
C10	0.0369 (11)	0.0632 (15)	0.0507 (14)	−0.0041 (10)	−0.0093 (10)	0.0208 (12)
C11	0.0378 (11)	0.0656 (15)	0.0572 (15)	0.0163 (11)	0.0031 (10)	0.0239 (13)
C12	0.0486 (12)	0.0514 (13)	0.0380 (12)	0.0166 (10)	0.0035 (9)	0.0067 (10)
C13	0.0377 (9)	0.0342 (10)	0.0283 (10)	−0.0010 (8)	0.0009 (8)	−0.0019 (8)
C14	0.0403 (11)	0.0357 (10)	0.0468 (13)	0.0004 (9)	0.0011 (9)	−0.0078 (9)
C15	0.0364 (14)	0.0334 (15)	0.056 (2)	0.000	−0.0102 (13)	0.000
N1	0.0323 (8)	0.0298 (8)	0.0250 (8)	0.0014 (6)	0.0021 (6)	0.0004 (6)
N2	0.0361 (8)	0.0388 (9)	0.0307 (9)	0.0075 (7)	0.0039 (7)	0.0040 (7)
O1	0.0567 (9)	0.0360 (7)	0.0320 (8)	−0.0025 (6)	0.0138 (6)	0.0001 (6)
O2	0.0795 (12)	0.0528 (10)	0.0653 (12)	−0.0019 (9)	0.0307 (10)	−0.0207 (9)
O3	0.0662 (16)	0.0286 (11)	0.0731 (18)	0.000	−0.0109 (12)	0.000
Zn1	0.0409 (2)	0.03008 (19)	0.0249 (2)	0.000	0.00062 (12)	0.000

C1—N1	1.324 (2)	C10—H10	0.9300
C1—C2	1.391 (3)	C11—C12	1.397 (3)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.355 (3)	C12—N2	1.333 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.405 (3)	C13—O1	1.277 (2)
C3—H3	0.9300	C13—C13i	1.420 (4)
C4—C5	1.412 (3)	C13—C14	1.462 (3)
C4—C6	1.424 (3)	C14—O2	1.229 (3)
C5—N1	1.358 (2)	C14—C15	1.498 (3)
C5—C9	1.433 (3)	C15—O3	1.229 (4)
C6—C7	1.351 (3)	C15—C14i	1.498 (3)
C6—H6	0.9300	N1—Zn1	2.1493 (15)
C7—C8	1.430 (3)	N2—Zn1	2.1664 (17)
C7—H7	0.9300	O1—Zn1	2.1325 (14)
C8—C10	1.400 (3)	Zn1—O1i	2.1325 (14)
C8—C9	1.406 (3)	Zn1—N1i	2.1493 (15)
C9—N2	1.357 (2)	Zn1—N2i	2.1664 (17)
C10—C11	1.359 (4)
N1—C1—C2	123.14 (19)	N2—C12—H12	119.0
N1—C1—H1	118.4	C11—C12—H12	119.0
C2—C1—H1	118.4	O1—C13—C13i	122.05 (11)
C3—C2—C1	118.91 (19)	O1—C13—C14	127.84 (18)
C3—C2—H2	120.5	C13i—C13—C14	110.10 (12)
C1—C2—H2	120.5	O2—C14—C13	127.8 (2)
C2—C3—C4	120.63 (19)	O2—C14—C15	126.6 (2)
C2—C3—H3	119.7	C13—C14—C15	105.61 (19)
C4—C3—H3	119.7	O3—C15—C14i	125.84 (13)
C3—C4—C5	116.54 (18)	O3—C15—C14	125.84 (13)
C3—C4—C6	124.48 (19)	C14i—C15—C14	108.3 (3)
C5—C4—C6	118.96 (18)	C1—N1—C5	118.26 (17)
N1—C5—C4	122.48 (17)	C1—N1—Zn1	128.09 (13)
N1—C5—C9	118.00 (17)	C5—N1—Zn1	113.65 (12)
C4—C5—C9	119.52 (17)	C12—N2—C9	118.54 (18)
C7—C6—C4	121.43 (19)	C12—N2—Zn1	128.01 (15)
C7—C6—H6	119.3	C9—N2—Zn1	113.37 (12)
C4—C6—H6	119.3	C13—O1—Zn1	107.30 (12)
C6—C7—C8	121.09 (19)	O1—Zn1—O1i	81.23 (7)
C6—C7—H7	119.5	O1—Zn1—N1	170.49 (6)
C8—C7—H7	119.5	O1i—Zn1—N1	94.20 (5)
C10—C8—C9	117.4 (2)	O1—Zn1—N1i	94.20 (5)
C10—C8—C7	123.7 (2)	O1i—Zn1—N1i	170.49 (6)
C9—C8—C7	118.88 (19)	N1—Zn1—N1i	91.48 (8)
N2—C9—C8	122.48 (18)	O1—Zn1—N2	94.54 (6)
N2—C9—C5	117.50 (17)	O1i—Zn1—N2	93.84 (6)
C8—C9—C5	120.02 (18)	N1—Zn1—N2	77.37 (6)
C11—C10—C8	119.6 (2)	N1i—Zn1—N2	94.83 (6)
C11—C10—H10	120.2	O1—Zn1—N2i	93.84 (6)
C8—C10—H10	120.2	O1i—Zn1—N2i	94.54 (6)
C10—C11—C12	119.9 (2)	N1—Zn1—N2i	94.83 (6)
C10—C11—H11	120.0	N1i—Zn1—N2i	77.37 (6)
C12—C11—H11	120.0	N2—Zn1—N2i	168.95 (9)
N2—C12—C11	121.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ii	0.93	2.47	3.295 (2)	149
C11—H11···O3iii	0.93	2.55	3.147 (2)	122

Table 1

Selected bond lengths (Å)

N1—Zn1	2.1493 (15)
N2—Zn1	2.1664 (17)
O1—Zn1	2.1325 (14)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.47	3.295 (2)	149
C11—H11⋯O3ii	0.93	2.55	3.147 (2)	122

Symmetry codes: (i) ; (ii) .