Bis{2-[(1H-pyrrol-2-yl)methyl-imino-meth-yl]phenolato-κN,O}zinc(II).

In the title compound, [Zn(C(12)H(11)N(2)O)(2)], the Zn(II) atom, lying on an inversion center, is coordinated by two O atoms and two N atoms from two salicylal Schiff base ligands in a distorted square-planar geometry. A three-dimensional network is formed by inter-molecular C-H⋯N hydrogen bonds and C-H⋯π contacts.

Related literature

For general background to Schiff base complexes, see: Qiu et al. (2006 ▶); Shi et al. (2007 ▶); Xiao et al. (2007a ▶,b ▶, 2008 ▶); You et al. (2006 ▶). For related structures, see: Qiu et al. (2004 ▶); You et al. (2004 ▶).

Experimental

Crystal data

[Zn(C12H11N2O)2]

M = 463.83

Triclinic,

a = 5.3443 (4) Å

b = 9.8669 (8) Å

c = 10.1392 (8) Å

α = 104.108 (1)°

β = 95.830 (1)°

γ = 100.126 (1)°

V = 504.58 (7) Å3

Z = 1

Mo Kα radiation

μ = 1.25 mm−1

T = 200 K

0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.706, T max = 0.789

6063 measured reflections

2455 independent reflections

2432 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.144

S = 1.11

2455 reflections

142 parameters

H-atom parameters constrained

Δρmax = 1.07 e Å−3

Δρmin = −0.73 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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/S1600536809034217/hy2222sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034217/hy2222Isup2.hkl

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

[Zn(C12H11N2O)2]	Z = 1
Mr = 463.83	F(000) = 240
Triclinic, P1	Dx = 1.526 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3443 (4) Å	Cell parameters from 2361 reflections
b = 9.8669 (8) Å	θ = 2.7–26.6°
c = 10.1392 (8) Å	µ = 1.25 mm−1
α = 104.108 (1)°	T = 200 K
β = 95.830 (1)°	Block, colorless
γ = 100.126 (1)°	0.30 × 0.30 × 0.20 mm
V = 504.58 (7) Å3

Bruker SMART APEX CCD diffractometer	2455 independent reflections
Radiation source: fine-focus sealed tube	2432 reflections with I > 2σ(I)
graphite	Rint = 0.047
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.706, Tmax = 0.789	k = −13→13
6063 measured 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0948P)2 + 0.2435P] where P = (Fo2 + 2Fc2)/3
2455 reflections	(Δ/σ)max < 0.001
142 parameters	Δρmax = 1.07 e Å−3
0 restraints	Δρmin = −0.73 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.8616 (5)	0.9132 (3)	0.3153 (2)	0.0297 (5)
C2	0.7761 (5)	0.7658 (3)	0.3046 (2)	0.0306 (5)
C3	0.8882 (6)	0.6636 (3)	0.2175 (3)	0.0379 (6)
H3	0.8295	0.5648	0.2088	0.045*
C4	1.0792 (6)	0.7055 (3)	0.1461 (3)	0.0392 (6)
H4	1.1518	0.6367	0.0880	0.047*
C5	1.1647 (6)	0.8508 (4)	0.1602 (3)	0.0403 (6)
H5	1.2984	0.8804	0.1120	0.048*
C6	1.0611 (5)	0.9518 (3)	0.2417 (3)	0.0363 (5)
H6	1.1246	1.0500	0.2491	0.044*
C7	0.5899 (5)	0.7143 (3)	0.3816 (3)	0.0320 (5)
H7	0.5492	0.6139	0.3688	0.038*
C8	0.2983 (5)	0.7075 (3)	0.5401 (3)	0.0331 (5)
H8A	0.1403	0.7464	0.5483	0.040*
H8B	0.2478	0.6061	0.4866	0.040*
C9	0.4297 (5)	0.7175 (3)	0.6791 (3)	0.0290 (5)
C10	0.3985 (5)	0.7807 (4)	0.8078 (3)	0.0398 (6)
H10	0.2724	0.8349	0.8336	0.048*
C11	0.5913 (6)	0.7507 (4)	0.8987 (3)	0.0447 (7)
H11	0.6185	0.7811	0.9964	0.054*
C12	0.7259 (6)	0.6713 (3)	0.8190 (3)	0.0405 (6)
H12	0.8665	0.6354	0.8519	0.049*
N1	0.4708 (4)	0.7890 (2)	0.4666 (2)	0.0297 (4)
N2	0.6319 (4)	0.6496 (2)	0.6837 (2)	0.0291 (4)
H2A	0.6901	0.6011	0.6127	0.035*
O1	0.7656 (4)	1.0126 (2)	0.3902 (2)	0.0346 (4)
Zn1	0.5000	1.0000	0.5000	0.02730 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0298 (11)	0.0310 (11)	0.0267 (10)	0.0055 (9)	−0.0013 (8)	0.0079 (9)
C2	0.0311 (11)	0.0325 (12)	0.0263 (10)	0.0053 (9)	−0.0014 (8)	0.0075 (9)
C3	0.0413 (14)	0.0378 (13)	0.0334 (12)	0.0112 (11)	0.0002 (10)	0.0074 (10)
C4	0.0384 (14)	0.0478 (15)	0.0307 (12)	0.0177 (11)	0.0042 (10)	0.0035 (11)
C5	0.0349 (13)	0.0527 (17)	0.0340 (13)	0.0124 (11)	0.0044 (10)	0.0110 (12)
C6	0.0331 (12)	0.0405 (13)	0.0353 (12)	0.0057 (10)	0.0047 (9)	0.0118 (10)
C7	0.0370 (12)	0.0265 (11)	0.0300 (11)	0.0048 (9)	0.0000 (9)	0.0062 (9)
C8	0.0350 (12)	0.0292 (11)	0.0318 (11)	−0.0022 (9)	−0.0009 (9)	0.0108 (9)
C9	0.0282 (11)	0.0285 (11)	0.0320 (11)	0.0050 (8)	0.0041 (8)	0.0123 (9)
C10	0.0311 (12)	0.0613 (18)	0.0306 (12)	0.0152 (12)	0.0082 (9)	0.0140 (12)
C11	0.0368 (14)	0.069 (2)	0.0317 (13)	0.0110 (13)	0.0041 (10)	0.0206 (13)
C12	0.0392 (14)	0.0448 (15)	0.0402 (14)	0.0106 (11)	−0.0011 (11)	0.0182 (12)
N1	0.0334 (10)	0.0272 (9)	0.0269 (9)	0.0031 (7)	0.0000 (7)	0.0085 (7)
N2	0.0327 (10)	0.0275 (9)	0.0292 (9)	0.0129 (8)	0.0035 (7)	0.0074 (7)
O1	0.0368 (9)	0.0299 (9)	0.0384 (9)	0.0067 (7)	0.0114 (7)	0.0096 (7)
Zn1	0.0300 (2)	0.0258 (2)	0.0259 (2)	0.00531 (15)	0.00390 (14)	0.00714 (15)

C1—O1	1.302 (3)	C8—N1	1.491 (3)
C1—C6	1.413 (4)	C8—H8A	0.9900
C1—C2	1.419 (4)	C8—H8B	0.9900
C2—C7	1.425 (4)	C9—C10	1.344 (4)
C2—C3	1.429 (4)	C9—N2	1.371 (3)
C3—C4	1.373 (4)	C10—C11	1.430 (4)
C3—H3	0.9500	C10—H10	0.9500
C4—C5	1.393 (5)	C11—C12	1.339 (5)
C4—H4	0.9500	C11—H11	0.9500
C5—C6	1.367 (4)	C12—N2	1.363 (3)
C5—H5	0.9500	C12—H12	0.9500
C6—H6	0.9500	N2—H2A	0.8800
C7—N1	1.287 (3)	Zn1—O1	1.8967 (19)
C7—H7	0.9500	Zn1—N1	2.001 (2)
C8—C9	1.481 (3)
O1—C1—C6	119.4 (2)	H8A—C8—H8B	108.1
O1—C1—C2	122.8 (2)	C10—C9—N2	109.4 (2)
C6—C1—C2	117.8 (3)	C10—C9—C8	134.5 (2)
C1—C2—C7	123.0 (2)	N2—C9—C8	116.1 (2)
C1—C2—C3	119.1 (2)	C9—C10—C11	106.9 (3)
C7—C2—C3	117.8 (2)	C9—C10—H10	126.6
C4—C3—C2	121.3 (3)	C11—C10—H10	126.6
C4—C3—H3	119.4	C12—C11—C10	106.5 (3)
C2—C3—H3	119.4	C12—C11—H11	126.8
C3—C4—C5	118.8 (3)	C10—C11—H11	126.8
C3—C4—H4	120.6	C11—C12—N2	110.1 (2)
C5—C4—H4	120.6	C11—C12—H12	124.9
C6—C5—C4	121.7 (3)	N2—C12—H12	124.9
C6—C5—H5	119.2	C7—N1—C8	115.6 (2)
C4—C5—H5	119.2	C7—N1—Zn1	124.25 (18)
C5—C6—C1	121.3 (3)	C8—N1—Zn1	120.09 (17)
C5—C6—H6	119.3	C12—N2—C9	107.1 (2)
C1—C6—H6	119.3	C12—N2—H2A	126.4
N1—C7—C2	127.1 (2)	C9—N2—H2A	126.4
N1—C7—H7	116.4	C1—O1—Zn1	130.68 (18)
C2—C7—H7	116.4	O1i—Zn1—O1	180.000 (1)
C9—C8—N1	110.58 (19)	O1i—Zn1—N1	88.44 (9)
C9—C8—H8A	109.5	O1—Zn1—N1	91.56 (9)
N1—C8—H8A	109.5	O1i—Zn1—N1i	91.56 (9)
C9—C8—H8B	109.5	O1—Zn1—N1i	88.44 (9)
N1—C8—H8B	109.5	N1—Zn1—N1i	180.00 (12)
O1—C1—C2—C7	−4.2 (4)	C9—C10—C11—C12	−0.1 (4)
C6—C1—C2—C7	175.2 (2)	C10—C11—C12—N2	0.3 (4)
O1—C1—C2—C3	178.6 (2)	C2—C7—N1—C8	−176.0 (2)
C6—C1—C2—C3	−2.0 (3)	C2—C7—N1—Zn1	5.3 (4)
C1—C2—C3—C4	1.1 (4)	C9—C8—N1—C7	98.0 (3)
C7—C2—C3—C4	−176.3 (2)	C9—C8—N1—Zn1	−83.2 (2)
C2—C3—C4—C5	0.4 (4)	C11—C12—N2—C9	−0.4 (3)
C3—C4—C5—C6	−0.8 (4)	C10—C9—N2—C12	0.3 (3)
C4—C5—C6—C1	−0.1 (4)	C8—C9—N2—C12	179.9 (2)
O1—C1—C6—C5	−179.0 (2)	C6—C1—O1—Zn1	179.70 (17)
C2—C1—C6—C5	1.6 (4)	C2—C1—O1—Zn1	−0.9 (4)
C1—C2—C7—N1	1.6 (4)	C1—O1—Zn1—N1	5.4 (2)
C3—C2—C7—N1	178.9 (2)	C1—O1—Zn1—N1i	−174.6 (2)
N1—C8—C9—C10	111.4 (3)	C7—N1—Zn1—O1i	172.7 (2)
N1—C8—C9—N2	−68.1 (3)	C8—N1—Zn1—O1i	−5.97 (17)
N2—C9—C10—C11	−0.1 (3)	C7—N1—Zn1—O1	−7.3 (2)
C8—C9—C10—C11	−179.6 (3)	C8—N1—Zn1—O1	174.03 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1i	0.99	2.26	2.770 (3)	111
C7—H7···N2ii	0.95	2.51	3.453 (3)	170
C6—H6···Cg1iii	0.95	2.73	3.624 (3)	158
C11—H11···Cg2iv	0.95	2.81	3.615 (3)	143

Table 1

Selected bond lengths (Å)

Zn1—O1	1.8967 (19)
Zn1—N1	2.001 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1i	0.99	2.26	2.770 (3)	111
C7—H7⋯N2ii	0.95	2.51	3.453 (3)	170
C6—H6⋯Cg1iii	0.95	2.73	3.624 (3)	158
C11—H11⋯Cg2iv	0.95	2.81	3.615 (3)	143

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 and Cg2 are the centroids of the N2,C9–C12 and C1–C6 rings, respectively.