Dibenzoatobis[3-(pyrrol-1-ylmeth-yl)pyridine]-zinc(II).

In the title compound, [Zn(C(7)H(5)O(2))(2)(C(10)H(10)N(2))(2)], the Zn(II) ion, located on a twofold axis, is coordinated by two N atoms from two 3-(pyrrol-1-ylmeth-yl)pyridine ligands and two O atoms from two benzoate ligands in a distorted tetra-hedral geometry. The pyridine and the pyrrole rings are nearly perpendicular to each other, making a dihedral angle of 84.83 (7)°.

Related literature

For examples of inter­actions between transition metal ions and biologically active mol­ecules, see: Daniele et al. (2008 ▶); Parkin (2004 ▶); Tshuva & Lippard (2004 ▶). For related structures, see: Lee et al. (2008 ▶); Park et al. (2008 ▶); Shin et al.(2009 ▶); Yu et al. (2008 ▶, 2009 ▶, 2010 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

[Zn(C7H5O2)2(C10H10N2)2]

M = 623.99

Monoclinic,

a = 14.4347 (14) Å

b = 9.4399 (9) Å

c = 11.1959 (11) Å

β = 102.896 (2)°

V = 1487.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.87 mm−1

T = 170 K

0.15 × 0.10 × 0.03 mm

Data collection

Bruker SMART CCD diffractometer

8090 measured reflections

2904 independent reflections

2204 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.071

S = 0.91

2904 reflections

195 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.51 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810028503/dn2587sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028503/dn2587Isup2.hkl

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

[Zn(C7H5O2)2(C10H10N2)2]	F(000) = 648
Mr = 623.99	Dx = 1.394 Mg m−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 2361 reflections
a = 14.4347 (14) Å	θ = 2.6–24.6°
b = 9.4399 (9) Å	µ = 0.87 mm−1
c = 11.1959 (11) Å	T = 170 K
β = 102.896 (2)°	Plate, colorless
V = 1487.1 (2) Å3	0.15 × 0.10 × 0.03 mm
Z = 2

Bruker SMART CCD diffractometer	2204 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.065
graphite	θmax = 26.0°, θmin = 2.2°
φ and ω scans	h = −9→17
8090 measured reflections	k = −11→11
2904 independent reflections	l = −13→13

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071	H-atom parameters constrained
S = 0.91	w = 1/[σ2(Fo2) + (0.0248P)2] where P = (Fo2 + 2Fc2)/3
2904 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.51 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
Zn1	0.5000	0.58373 (4)	0.7500	0.02372 (12)
O11	0.39278 (9)	0.51333 (15)	0.63040 (12)	0.0289 (4)
O12	0.36133 (10)	0.38352 (16)	0.78176 (13)	0.0376 (4)
C11	0.33872 (14)	0.4306 (2)	0.67596 (19)	0.0259 (5)
C12	0.24503 (14)	0.3958 (2)	0.59353 (18)	0.0241 (5)
C13	0.22904 (14)	0.4186 (2)	0.46787 (18)	0.0294 (5)
H13	0.2794	0.4511	0.4330	0.035*
C14	0.14056 (16)	0.3944 (2)	0.3935 (2)	0.0364 (6)
H14	0.1303	0.4094	0.3076	0.044*
C15	0.06679 (16)	0.3482 (2)	0.4441 (2)	0.0395 (6)
H15	0.0056	0.3330	0.3930	0.047*
C16	0.08190 (16)	0.3240 (3)	0.5688 (2)	0.0387 (6)
H16	0.0311	0.2924	0.6034	0.046*
C17	0.17063 (15)	0.3458 (2)	0.6428 (2)	0.0310 (5)
H17	0.1813	0.3266	0.7281	0.037*
N21	0.45103 (11)	0.72476 (17)	0.86239 (14)	0.0238 (4)
N22	0.22689 (12)	1.08801 (19)	0.91482 (16)	0.0316 (4)
C21	0.48598 (14)	0.7216 (2)	0.98335 (18)	0.0258 (5)
H21	0.5324	0.6523	1.0162	0.031*
C22	0.45709 (15)	0.8149 (2)	1.06183 (19)	0.0325 (5)
H22	0.4824	0.8088	1.1476	0.039*
C23	0.39112 (15)	0.9174 (2)	1.01497 (19)	0.0328 (5)
H23	0.3708	0.9829	1.0682	0.039*
C24	0.35458 (14)	0.9243 (2)	0.88950 (19)	0.0283 (5)
C25	0.38588 (14)	0.8249 (2)	0.81762 (18)	0.0258 (5)
H25	0.3602	0.8270	0.7318	0.031*
C26	0.28375 (16)	1.0365 (2)	0.8315 (2)	0.0380 (6)
H26A	0.3184	1.1171	0.8053	0.046*
H26B	0.2410	0.9966	0.7576	0.046*
C27	0.24005 (15)	1.2131 (2)	0.9763 (2)	0.0337 (5)
H27	0.2843	1.2847	0.9675	0.040*
C28	0.17895 (16)	1.2179 (3)	1.0527 (2)	0.0389 (6)
H28	0.1725	1.2932	1.1065	0.047*
C29	0.12722 (16)	1.0912 (3)	1.0374 (2)	0.0443 (6)
H29	0.0790	1.0649	1.0786	0.053*
C30	0.15875 (16)	1.0129 (3)	0.9527 (2)	0.0429 (6)
H30	0.1368	0.9212	0.9248	0.051*

	U11	U22	U33	U12	U13	U23
Zn1	0.0232 (2)	0.0247 (2)	0.0228 (2)	0.000	0.00434 (14)	0.000
O11	0.0247 (8)	0.0311 (9)	0.0300 (8)	−0.0069 (7)	0.0045 (7)	−0.0004 (7)
O12	0.0319 (9)	0.0500 (11)	0.0286 (9)	−0.0016 (7)	0.0017 (7)	0.0079 (7)
C11	0.0262 (12)	0.0236 (12)	0.0279 (12)	0.0047 (10)	0.0060 (9)	−0.0044 (10)
C12	0.0244 (11)	0.0186 (11)	0.0291 (12)	0.0026 (9)	0.0053 (9)	−0.0004 (9)
C13	0.0300 (12)	0.0264 (12)	0.0319 (12)	−0.0026 (10)	0.0073 (10)	−0.0006 (10)
C14	0.0398 (14)	0.0333 (14)	0.0307 (13)	−0.0035 (11)	−0.0039 (11)	0.0008 (10)
C15	0.0244 (13)	0.0347 (14)	0.0524 (16)	−0.0013 (11)	−0.0066 (11)	−0.0031 (12)
C16	0.0274 (13)	0.0373 (14)	0.0528 (16)	−0.0030 (11)	0.0121 (12)	−0.0014 (12)
C17	0.0303 (13)	0.0293 (12)	0.0337 (13)	0.0007 (10)	0.0078 (10)	0.0015 (10)
N21	0.0230 (10)	0.0257 (10)	0.0228 (9)	−0.0016 (7)	0.0054 (7)	0.0014 (8)
N22	0.0309 (10)	0.0248 (10)	0.0403 (11)	0.0040 (9)	0.0104 (8)	0.0000 (9)
C21	0.0243 (12)	0.0289 (12)	0.0240 (12)	0.0007 (9)	0.0051 (9)	0.0047 (10)
C22	0.0374 (14)	0.0400 (14)	0.0196 (11)	−0.0015 (11)	0.0052 (10)	0.0004 (10)
C23	0.0416 (14)	0.0297 (12)	0.0290 (12)	0.0012 (11)	0.0121 (10)	−0.0053 (11)
C24	0.0312 (12)	0.0252 (12)	0.0296 (12)	0.0010 (10)	0.0094 (10)	0.0008 (10)
C25	0.0266 (12)	0.0290 (12)	0.0209 (11)	0.0006 (10)	0.0038 (9)	0.0017 (10)
C26	0.0456 (15)	0.0331 (14)	0.0367 (14)	0.0114 (11)	0.0122 (12)	0.0002 (11)
C27	0.0319 (13)	0.0268 (13)	0.0417 (14)	0.0008 (10)	0.0070 (11)	−0.0017 (11)
C28	0.0350 (15)	0.0418 (15)	0.0410 (14)	0.0066 (11)	0.0107 (12)	−0.0063 (12)
C29	0.0298 (13)	0.0471 (16)	0.0604 (17)	0.0038 (12)	0.0197 (12)	0.0083 (14)
C30	0.0353 (15)	0.0275 (14)	0.0649 (18)	−0.0029 (11)	0.0093 (13)	−0.0004 (12)

Zn1—O11i	1.9248 (13)	N22—C27	1.359 (3)
Zn1—O11	1.9248 (13)	N22—C26	1.457 (3)
Zn1—N21i	2.0621 (16)	C21—C22	1.373 (3)
Zn1—N21	2.0621 (16)	C21—H21	0.9500
O11—C11	1.287 (2)	C22—C23	1.377 (3)
O12—C11	1.239 (2)	C22—H22	0.9500
C11—C12	1.494 (3)	C23—C24	1.387 (3)
C12—C13	1.391 (3)	C23—H23	0.9500
C12—C17	1.395 (3)	C24—C25	1.376 (3)
C13—C14	1.379 (3)	C24—C26	1.514 (3)
C13—H13	0.9500	C25—H25	0.9500
C14—C15	1.383 (3)	C26—H26A	0.9900
C14—H14	0.9500	C26—H26B	0.9900
C15—C16	1.384 (3)	C27—C28	1.359 (3)
C15—H15	0.9500	C27—H27	0.9500
C16—C17	1.377 (3)	C28—C29	1.400 (3)
C16—H16	0.9500	C28—H28	0.9500
C17—H17	0.9500	C29—C30	1.359 (3)
N21—C21	1.336 (2)	C29—H29	0.9500
N21—C25	1.349 (2)	C30—H30	0.9500
N22—C30	1.355 (3)
O11i—Zn1—O11	139.60 (9)	N21—C21—C22	122.29 (19)
O11i—Zn1—N21i	108.40 (6)	N21—C21—H21	118.9
O11—Zn1—N21i	97.49 (6)	C22—C21—H21	118.9
O11i—Zn1—N21	97.48 (6)	C21—C22—C23	119.3 (2)
O11—Zn1—N21	108.39 (6)	C21—C22—H22	120.3
N21i—Zn1—N21	99.58 (9)	C23—C22—H22	120.3
C11—O11—Zn1	113.47 (13)	C22—C23—C24	119.6 (2)
O12—C11—O11	122.87 (19)	C22—C23—H23	120.2
O12—C11—C12	121.42 (19)	C24—C23—H23	120.2
O11—C11—C12	115.70 (18)	C25—C24—C23	117.37 (19)
C13—C12—C17	118.95 (19)	C25—C24—C26	120.30 (18)
C13—C12—C11	120.95 (18)	C23—C24—C26	122.32 (19)
C17—C12—C11	120.04 (18)	N21—C25—C24	123.58 (18)
C14—C13—C12	120.5 (2)	N21—C25—H25	118.2
C14—C13—H13	119.8	C24—C25—H25	118.2
C12—C13—H13	119.8	N22—C26—C24	112.46 (17)
C13—C14—C15	119.9 (2)	N22—C26—H26A	109.1
C13—C14—H14	120.0	C24—C26—H26A	109.1
C15—C14—H14	120.0	N22—C26—H26B	109.1
C14—C15—C16	120.2 (2)	C24—C26—H26B	109.1
C14—C15—H15	119.9	H26A—C26—H26B	107.8
C16—C15—H15	119.9	N22—C27—C28	108.1 (2)
C17—C16—C15	119.9 (2)	N22—C27—H27	125.9
C17—C16—H16	120.0	C28—C27—H27	125.9
C15—C16—H16	120.0	C27—C28—C29	107.3 (2)
C16—C17—C12	120.5 (2)	C27—C28—H28	126.3
C16—C17—H17	119.8	C29—C28—H28	126.3
C12—C17—H17	119.8	C30—C29—C28	107.3 (2)
C21—N21—C25	117.83 (17)	C30—C29—H29	126.3
C21—N21—Zn1	120.05 (14)	C28—C29—H29	126.3
C25—N21—Zn1	122.09 (13)	N22—C30—C29	108.3 (2)
C30—N22—C27	108.97 (18)	N22—C30—H30	125.9
C30—N22—C26	125.30 (19)	C29—C30—H30	125.9
C27—N22—C26	125.43 (19)
O11i—Zn1—O11—C11	56.95 (13)	N21i—Zn1—N21—C25	56.41 (14)
N21i—Zn1—O11—C11	−172.84 (13)	C25—N21—C21—C22	0.7 (3)
N21—Zn1—O11—C11	−70.10 (14)	Zn1—N21—C21—C22	178.71 (15)
Zn1—O11—C11—O12	−10.7 (3)	N21—C21—C22—C23	−1.2 (3)
Zn1—O11—C11—C12	168.33 (12)	C21—C22—C23—C24	0.3 (3)
O12—C11—C12—C13	−164.0 (2)	C22—C23—C24—C25	1.0 (3)
O11—C11—C12—C13	17.0 (3)	C22—C23—C24—C26	−178.4 (2)
O12—C11—C12—C17	18.9 (3)	C21—N21—C25—C24	0.8 (3)
O11—C11—C12—C17	−160.13 (18)	Zn1—N21—C25—C24	−177.24 (15)
C17—C12—C13—C14	1.1 (3)	C23—C24—C25—N21	−1.6 (3)
C11—C12—C13—C14	−176.02 (19)	C26—C24—C25—N21	177.83 (19)
C12—C13—C14—C15	0.5 (3)	C30—N22—C26—C24	−70.4 (3)
C13—C14—C15—C16	−1.1 (3)	C27—N22—C26—C24	102.6 (2)
C14—C15—C16—C17	−0.1 (4)	C25—C24—C26—N22	153.59 (19)
C15—C16—C17—C12	1.8 (3)	C23—C24—C26—N22	−27.0 (3)
C13—C12—C17—C16	−2.3 (3)	C30—N22—C27—C28	−0.7 (3)
C11—C12—C17—C16	174.9 (2)	C26—N22—C27—C28	−174.69 (19)
O11i—Zn1—N21—C21	−11.37 (15)	N22—C27—C28—C29	0.2 (3)
O11—Zn1—N21—C21	137.18 (14)	C27—C28—C29—C30	0.3 (3)
N21i—Zn1—N21—C21	−121.55 (16)	C27—N22—C30—C29	0.9 (3)
O11i—Zn1—N21—C25	166.58 (15)	C26—N22—C30—C29	174.90 (19)
O11—Zn1—N21—C25	−44.86 (16)	C28—C29—C30—N22	−0.8 (3)