Bis{5-meth-oxy-2-[(1H-pyrrol-2-yl)methyl-imino-meth-yl]phenolato}zinc(II).

The title compound, [Zn(C(13)H(13)N(2)O(2))(2)], contains a Zn(II) centre, located on a twofold rotation axis, that is coordinated by two O atoms and two N atoms from two salicylal Schiff base mol-ecules. The crystal structure is stabilized by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the importance of zinc derivatives in biological processes, see: Chen et al. (2007 ▶); Xiao & Xiao (2008 ▶); Xiao et al. (2007 ▶, 2008 ▶). For related structures, see: You & Zhu (2006 ▶); Zhu et al. (2004 ▶); Qiu et al. (2004 ▶).

Experimental

Crystal data

[Zn(C13n class="Species">H13N2O2)2]

M = 523.88

Monoclinic,

a = 27.210 (4) Å

b = 5.2239 (9) Å

c = 24.335 (3) Å

β = 137.179 (9)°

V = 2351.1 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.09 mm−1

T = 298 K

0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.736, T max = 0.812

8100 measured reflections

2881 independent reflections

2429 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.154

S = 1.08

2881 reflections

160 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.57 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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/S1600536809032784/hg2551sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032784/hg2551Isup2.hkl

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

[Zn(C13H13N2O2)2]	F(000) = 1088
Mr = 523.88	Dx = 1.480 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2301 reflections
a = 27.210 (4) Å	θ = 2.5–26.1°
b = 5.2239 (9) Å	µ = 1.09 mm−1
c = 24.335 (3) Å	T = 298 K
β = 137.179 (9)°	Block, colorless
V = 2351.1 (6) Å3	0.30 × 0.30 × 0.20 mm
Z = 4

Bruker SMART APEX area-detector diffractometer	2881 independent reflections
Radiation source: fine-focus sealed tube	2429 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −36→35
Tmin = 0.736, Tmax = 0.812	k = −6→6
8100 measured reflections	l = −26→32

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0814P)2 + 2.3252P] where P = (Fo2 + 2Fc2)/3
2881 reflections	(Δ/σ)max < 0.001
160 parameters	Δρmax = 0.72 e Å−3
0 restraints	Δρmin = −0.57 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
C1	0.93603 (16)	0.2495 (6)	0.29548 (18)	0.0401 (6)
C2	0.87592 (16)	0.4163 (6)	0.24129 (18)	0.0398 (6)
C3	0.81985 (18)	0.3941 (7)	0.2349 (2)	0.0503 (8)
H3	0.7802	0.5026	0.1996	0.060*
C4	0.82168 (18)	0.2211 (7)	0.2782 (2)	0.0550 (8)
H4	0.7838	0.2105	0.2720	0.066*
C5	0.8813 (2)	0.0602 (7)	0.3317 (2)	0.0490 (8)
C6	0.93736 (19)	0.0707 (6)	0.3401 (2)	0.0462 (7)
H6	0.9763	−0.0409	0.3754	0.055*
C7	0.9380 (2)	−0.2809 (8)	0.4279 (2)	0.0673 (10)
H7A	0.9385	−0.3953	0.3973	0.101*
H7B	0.9317	−0.3774	0.4559	0.101*
H7C	0.9830	−0.1896	0.4663	0.101*
C8	0.86588 (16)	0.6031 (6)	0.19107 (18)	0.0418 (7)
H8	0.8240	0.7009	0.1592	0.050*
C9	0.88198 (18)	0.8391 (7)	0.1226 (2)	0.0507 (8)
H9A	0.9208	0.9554	0.1449	0.061*
H9B	0.8430	0.9389	0.1065	0.061*
C10	0.85569 (18)	0.7069 (7)	0.0508 (2)	0.0523 (8)
C11	0.8621 (2)	0.7591 (13)	0.0026 (3)	0.0938 (18)
H11	0.8869	0.8941	0.0066	0.113*
C12	0.8210 (3)	0.5539 (14)	−0.0582 (3)	0.103 (2)
H12	0.8155	0.5318	−0.1004	0.123*
C13	0.7934 (3)	0.4069 (13)	−0.0421 (3)	0.103 (2)
H13	0.7646	0.2637	−0.0717	0.124*
N1	0.90797 (13)	0.6538 (5)	0.18427 (15)	0.0398 (5)
N2	0.81349 (18)	0.4967 (6)	0.02362 (19)	0.0571 (8)
H2	0.8016	0.4320	0.0451	0.069*
O1	0.99094 (12)	0.2514 (5)	0.30668 (15)	0.0552 (6)
O2	0.88016 (16)	−0.1038 (6)	0.37455 (17)	0.0663 (7)
Zn1	1.0000	0.46424 (10)	0.2500	0.0430 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0412 (15)	0.0449 (16)	0.0473 (16)	−0.0004 (12)	0.0366 (14)	−0.0027 (13)
C2	0.0376 (14)	0.0469 (17)	0.0450 (16)	−0.0015 (12)	0.0334 (14)	−0.0038 (13)
C3	0.0426 (16)	0.065 (2)	0.0567 (19)	0.0051 (15)	0.0406 (16)	0.0019 (16)
C4	0.0501 (18)	0.073 (2)	0.065 (2)	−0.0037 (17)	0.0497 (18)	−0.0036 (18)
C5	0.058 (2)	0.0520 (18)	0.0553 (19)	−0.0101 (15)	0.0475 (18)	−0.0071 (15)
C6	0.0513 (18)	0.0469 (17)	0.0528 (18)	0.0015 (14)	0.0421 (16)	0.0016 (14)
C7	0.086 (3)	0.060 (2)	0.067 (2)	−0.011 (2)	0.059 (2)	0.0029 (19)
C8	0.0363 (14)	0.0465 (16)	0.0448 (16)	0.0037 (12)	0.0304 (14)	−0.0004 (13)
C9	0.0515 (18)	0.0459 (18)	0.060 (2)	−0.0014 (14)	0.0424 (17)	0.0043 (15)
C10	0.0449 (17)	0.067 (2)	0.0499 (18)	0.0130 (15)	0.0363 (16)	0.0157 (16)
C11	0.067 (3)	0.156 (5)	0.081 (3)	0.038 (3)	0.061 (3)	0.049 (3)
C12	0.081 (4)	0.168 (6)	0.059 (3)	0.047 (4)	0.051 (3)	0.013 (3)
C13	0.091 (4)	0.114 (5)	0.060 (3)	0.025 (3)	0.042 (3)	−0.013 (3)
N1	0.0355 (12)	0.0458 (13)	0.0423 (13)	−0.0016 (10)	0.0298 (11)	−0.0022 (11)
N2	0.0605 (19)	0.0552 (18)	0.0486 (16)	−0.0063 (13)	0.0378 (16)	−0.0074 (13)
O1	0.0481 (12)	0.0674 (15)	0.0712 (15)	0.0150 (11)	0.0504 (13)	0.0210 (12)
O2	0.0821 (18)	0.0695 (17)	0.0832 (19)	−0.0025 (15)	0.0719 (17)	0.0089 (15)
Zn1	0.0374 (3)	0.0513 (3)	0.0530 (3)	0.000	0.0372 (3)	0.000

C1—O1	1.308 (3)	C9—N1	1.460 (4)
C1—C6	1.412 (4)	C9—C10	1.487 (5)
C1—C2	1.417 (4)	C9—H9A	0.9700
C2—C3	1.421 (4)	C9—H9B	0.9700
C2—C8	1.425 (4)	C10—C11	1.333 (5)
C3—C4	1.360 (5)	C10—N2	1.359 (5)
C3—H3	0.9300	C11—C12	1.471 (8)
C4—C5	1.391 (5)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.318 (9)
C5—O2	1.367 (4)	C12—H12	0.9300
C5—C6	1.384 (5)	C13—N2	1.340 (6)
C6—H6	0.9300	C13—H13	0.9300
C7—O2	1.422 (5)	N1—Zn1	1.983 (2)
C7—H7A	0.9600	N2—H2	0.8600
C7—H7B	0.9600	O1—Zn1	1.923 (2)
C7—H7C	0.9600	Zn1—O1i	1.923 (2)
C8—N1	1.299 (4)	Zn1—N1i	1.983 (2)
C8—H8	0.9300
O1—C1—C6	117.6 (3)	N1—C9—H9B	109.5
O1—C1—C2	123.5 (3)	C10—C9—H9B	109.5
C6—C1—C2	118.9 (3)	H9A—C9—H9B	108.1
C1—C2—C3	117.7 (3)	C11—C10—N2	110.3 (4)
C1—C2—C8	125.7 (3)	C11—C10—C9	132.7 (4)
C3—C2—C8	116.6 (3)	N2—C10—C9	116.9 (3)
C4—C3—C2	122.9 (3)	C10—C11—C12	104.0 (5)
C4—C3—H3	118.6	C10—C11—H11	128.0
C2—C3—H3	118.6	C12—C11—H11	128.0
C3—C4—C5	118.8 (3)	C13—C12—C11	107.7 (5)
C3—C4—H4	120.6	C13—C12—H12	126.1
C5—C4—H4	120.6	C11—C12—H12	126.1
O2—C5—C6	123.5 (3)	C12—C13—N2	109.2 (6)
O2—C5—C4	115.5 (3)	C12—C13—H13	125.4
C6—C5—C4	121.1 (3)	N2—C13—H13	125.4
C5—C6—C1	120.6 (3)	C8—N1—C9	117.3 (3)
C5—C6—H6	119.7	C8—N1—Zn1	120.3 (2)
C1—C6—H6	119.7	C9—N1—Zn1	122.2 (2)
O2—C7—H7A	109.5	C13—N2—C10	108.8 (5)
O2—C7—H7B	109.5	C13—N2—H2	125.6
H7A—C7—H7B	109.5	C10—N2—H2	125.6
O2—C7—H7C	109.5	C1—O1—Zn1	125.7 (2)
H7A—C7—H7C	109.5	C5—O2—C7	118.3 (3)
H7B—C7—H7C	109.5	O1—Zn1—O1i	109.36 (15)
N1—C8—C2	128.1 (3)	O1—Zn1—N1i	117.41 (10)
N1—C8—H8	116.0	O1i—Zn1—N1i	96.71 (10)
C2—C8—H8	116.0	O1—Zn1—N1	96.71 (10)
N1—C9—C10	110.7 (3)	O1i—Zn1—N1	117.41 (10)
N1—C9—H9A	109.5	N1i—Zn1—N1	120.10 (15)
C10—C9—H9A	109.5
O1—C1—C2—C3	−180.0 (3)	C2—C8—N1—C9	174.4 (3)
C6—C1—C2—C3	0.1 (4)	C2—C8—N1—Zn1	−1.1 (4)
O1—C1—C2—C8	1.2 (5)	C10—C9—N1—C8	−102.9 (3)
C6—C1—C2—C8	−178.8 (3)	C10—C9—N1—Zn1	72.5 (3)
C1—C2—C3—C4	−0.1 (5)	C12—C13—N2—C10	−0.4 (6)
C8—C2—C3—C4	178.8 (3)	C11—C10—N2—C13	1.4 (5)
C2—C3—C4—C5	0.7 (5)	C9—C10—N2—C13	178.5 (4)
C3—C4—C5—O2	178.3 (3)	C6—C1—O1—Zn1	177.0 (2)
C3—C4—C5—C6	−1.3 (5)	C2—C1—O1—Zn1	−3.0 (5)
O2—C5—C6—C1	−178.3 (3)	C6—C5—O2—C7	−3.0 (5)
C4—C5—C6—C1	1.3 (5)	C4—C5—O2—C7	177.4 (3)
O1—C1—C6—C5	179.4 (3)	C1—O1—Zn1—O1i	−119.8 (3)
C2—C1—C6—C5	−0.7 (5)	C1—O1—Zn1—N1i	131.4 (3)
C1—C2—C8—N1	1.1 (5)	C1—O1—Zn1—N1	2.4 (3)
C3—C2—C8—N1	−177.8 (3)	C8—N1—Zn1—O1	−0.4 (3)
N1—C9—C10—C11	−139.4 (4)	C9—N1—Zn1—O1	−175.6 (2)
N1—C9—C10—N2	44.4 (4)	C8—N1—Zn1—O1i	115.5 (2)
N2—C10—C11—C12	−1.7 (4)	C9—N1—Zn1—O1i	−59.7 (3)
C9—C10—C11—C12	−178.1 (4)	C8—N1—Zn1—N1i	−127.6 (3)
C10—C11—C12—C13	1.4 (6)	C9—N1—Zn1—N1i	57.2 (2)
C11—C12—C13—N2	−0.6 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1ii	0.97	2.32	3.291 (4)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1i	0.97	2.32	3.291 (4)	177

Symmetry code: (i) .