Bis(3-hydroxy-pyridine-κN)bis-(3-nitro-benzoato-κO)zinc(II).

The title complex, [Zn(C(7)H(4)NO(4))(2)(C(5)H(5)NO)(2)], has site symmetry 2. The Zn(II) ion is located on a crystallographic twofold rotation axis and assumes a distorted tetra-hedral ZnN(2)O(2) coordination geometry. Mol-ecules are linked by an inter-molecular O-H⋯O hydrogen bond and π-π stacking inter-actions between pyridine rings [centroid-centroid speparation 3.594 (1) Å].

Related literature

For general background, see: Su & Xu (2004 ▶); Xu et al. (2007 ▶). For a related structure, see: Yan et al. (2008 ▶).

Experimental

Crystal data

[Zn(C7H4NO4)2(C5H5NO)2]

M = 587.79

Monoclinic,

a = 22.992 (4) Å

b = 7.2412 (12) Å

c = 15.797 (3) Å

β = 111.584 (5)°

V = 2445.6 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.07 mm−1

T = 294 K

0.33 × 0.30 × 0.24 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.655, T max = 0.770

10172 measured reflections

2179 independent reflections

2038 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.080

S = 1.18

2179 reflections

177 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.37 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027147/bx2223sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027147/bx2223Isup2.hkl

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

[Zn(C7H4NO4)2(C5H5NO)2]	F(000) = 1200
Mr = 587.79	Dx = 1.596 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2092 reflections
a = 22.992 (4) Å	θ = 2.0–25.0°
b = 7.2412 (12) Å	µ = 1.07 mm−1
c = 15.797 (3) Å	T = 294 K
β = 111.584 (5)°	Block, colourless
V = 2445.6 (8) Å3	0.33 × 0.30 × 0.24 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	2179 independent reflections
Radiation source: fine-focus sealed tube	2038 reflections with I > 2σ(I)
graphite	Rint = 0.023
Detector resolution: 10.0 pixels mm-1	θmax = 25.2°, θmin = 1.9°
ω scans	h = −27→27
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −7→8
Tmin = 0.655, Tmax = 0.770	l = −18→18
10172 measured reflections

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 1.18	w = 1/[σ2(Fo2) + (0.0461P)2 + 1.01P] where P = (Fo2 + 2Fc2)/3
2179 reflections	(Δ/σ)max < 0.001
177 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.37 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
Zn	0.5000	0.60825 (4)	0.2500	0.03308 (13)
N1	0.51519 (7)	0.4295 (2)	0.15973 (11)	0.0353 (4)
N2	0.76573 (8)	0.9962 (2)	0.57621 (11)	0.0428 (4)
O1	0.41195 (6)	0.2005 (2)	−0.04113 (10)	0.0502 (4)
H1A	0.4151	0.1741	−0.0959	0.075*
O2	0.57415 (6)	0.7413 (2)	0.32834 (9)	0.0430 (3)
O3	0.57500 (8)	0.8529 (3)	0.19867 (10)	0.0582 (4)
O4	0.73267 (8)	0.9305 (3)	0.61402 (11)	0.0597 (4)
O5	0.81810 (8)	1.0587 (3)	0.61763 (12)	0.0639 (5)
C1	0.46440 (9)	0.3618 (3)	0.09435 (13)	0.0376 (4)
H1	0.4256	0.3830	0.0983	0.045*
C2	0.46675 (9)	0.2612 (3)	0.02073 (12)	0.0360 (4)
C3	0.52475 (9)	0.2297 (3)	0.01547 (13)	0.0386 (4)
H3	0.5283	0.1659	−0.0335	0.046*
C4	0.57718 (9)	0.2956 (3)	0.08477 (14)	0.0442 (5)
H4	0.6166	0.2729	0.0834	0.053*
C5	0.57162 (9)	0.3943 (3)	0.15562 (14)	0.0402 (5)
H5	0.6075	0.4377	0.2016	0.048*
C6	0.59870 (9)	0.8367 (3)	0.28242 (13)	0.0376 (4)
C7	0.66049 (9)	0.9261 (3)	0.33534 (13)	0.0341 (4)
C8	0.68297 (9)	0.9269 (3)	0.43004 (13)	0.0341 (4)
H8	0.6590	0.8799	0.4613	0.041*
C9	0.74167 (9)	0.9988 (3)	0.47648 (12)	0.0355 (4)
C10	0.77887 (9)	1.0701 (3)	0.43250 (15)	0.0434 (5)
H10	0.8185	1.1168	0.4654	0.052*
C11	0.75552 (11)	1.0701 (3)	0.33837 (16)	0.0491 (5)
H11	0.7795	1.1182	0.3073	0.059*
C12	0.69704 (10)	0.9994 (3)	0.29032 (14)	0.0426 (5)
H12	0.6818	1.0006	0.2270	0.051*

	U11	U22	U33	U12	U13	U23
Zn	0.03108 (18)	0.0418 (2)	0.02401 (18)	0.000	0.00732 (12)	0.000
N1	0.0354 (8)	0.0405 (9)	0.0294 (8)	0.0019 (7)	0.0112 (7)	−0.0008 (6)
N2	0.0417 (9)	0.0484 (11)	0.0331 (9)	0.0088 (8)	0.0074 (8)	−0.0057 (7)
O1	0.0417 (8)	0.0636 (10)	0.0403 (8)	−0.0044 (7)	0.0091 (6)	−0.0163 (7)
O2	0.0361 (7)	0.0557 (9)	0.0345 (7)	−0.0105 (6)	0.0097 (6)	−0.0003 (6)
O3	0.0593 (10)	0.0789 (11)	0.0279 (8)	−0.0163 (8)	0.0061 (7)	−0.0030 (7)
O4	0.0613 (10)	0.0864 (13)	0.0321 (8)	0.0003 (9)	0.0181 (8)	−0.0025 (8)
O5	0.0444 (9)	0.0838 (12)	0.0466 (9)	−0.0016 (8)	−0.0031 (7)	−0.0135 (9)
C1	0.0326 (9)	0.0459 (11)	0.0346 (10)	0.0012 (8)	0.0128 (8)	−0.0037 (8)
C2	0.0387 (10)	0.0363 (10)	0.0311 (9)	−0.0001 (8)	0.0107 (8)	−0.0001 (8)
C3	0.0471 (11)	0.0372 (10)	0.0358 (10)	0.0031 (8)	0.0201 (9)	−0.0017 (8)
C4	0.0369 (10)	0.0519 (13)	0.0477 (12)	0.0064 (9)	0.0203 (9)	−0.0001 (10)
C5	0.0323 (9)	0.0470 (12)	0.0376 (11)	0.0017 (8)	0.0086 (8)	−0.0014 (8)
C6	0.0374 (10)	0.0423 (11)	0.0313 (10)	−0.0018 (8)	0.0106 (8)	−0.0048 (8)
C7	0.0366 (10)	0.0374 (10)	0.0292 (9)	−0.0012 (8)	0.0131 (8)	−0.0014 (7)
C8	0.0339 (9)	0.0399 (10)	0.0310 (10)	−0.0013 (8)	0.0148 (8)	−0.0011 (7)
C9	0.0359 (9)	0.0382 (10)	0.0310 (10)	0.0033 (8)	0.0106 (8)	−0.0036 (8)
C10	0.0329 (10)	0.0482 (12)	0.0478 (12)	−0.0067 (9)	0.0133 (9)	−0.0054 (9)
C11	0.0477 (12)	0.0589 (14)	0.0498 (13)	−0.0082 (10)	0.0287 (10)	0.0030 (10)
C12	0.0491 (11)	0.0501 (12)	0.0322 (10)	−0.0043 (9)	0.0193 (9)	0.0011 (9)

Zn—N1	2.0486 (16)	C3—C4	1.381 (3)
Zn—N1i	2.0486 (16)	C3—H3	0.9300
Zn—O2	1.9527 (13)	C4—C5	1.373 (3)
Zn—O2i	1.9527 (13)	C4—H4	0.9300
N1—C1	1.335 (2)	C5—H5	0.9300
N1—C5	1.347 (3)	C6—C7	1.504 (3)
N2—O4	1.223 (2)	C7—C12	1.390 (3)
N2—O5	1.226 (2)	C7—C8	1.392 (3)
N2—C9	1.465 (3)	C8—C9	1.379 (3)
O1—C2	1.353 (2)	C8—H8	0.9300
O1—H1A	0.9147	C9—C10	1.385 (3)
O2—C6	1.274 (2)	C10—C11	1.383 (3)
O3—C6	1.237 (2)	C10—H10	0.9300
C1—C2	1.390 (3)	C11—C12	1.377 (3)
C1—H1	0.9300	C11—H11	0.9300
C2—C3	1.385 (3)	C12—H12	0.9300
O2—Zn—O2i	120.90 (9)	C3—C4—H4	119.7
O2—Zn—N1	114.84 (6)	N1—C5—C4	121.20 (18)
O2i—Zn—N1	101.72 (6)	N1—C5—H5	119.4
O2—Zn—N1i	101.72 (6)	C4—C5—H5	119.4
O2i—Zn—N1i	114.84 (6)	O3—C6—O2	123.17 (18)
N1—Zn—N1i	101.64 (9)	O3—C6—C7	120.52 (18)
C1—N1—C5	118.48 (16)	O2—C6—C7	116.28 (16)
C1—N1—Zn	116.48 (12)	C12—C7—C8	119.53 (18)
C5—N1—Zn	124.53 (13)	C12—C7—C6	120.34 (17)
O4—N2—O5	123.22 (18)	C8—C7—C6	120.03 (17)
O4—N2—C9	118.26 (17)	C9—C8—C7	118.50 (17)
O5—N2—C9	118.52 (18)	C9—C8—H8	120.8
C2—O1—H1A	112.0	C7—C8—H8	120.8
C6—O2—Zn	111.90 (12)	C8—C9—C10	122.55 (18)
N1—C1—C2	123.20 (17)	C8—C9—N2	118.40 (17)
N1—C1—H1	118.4	C10—C9—N2	119.04 (17)
C2—C1—H1	118.4	C11—C10—C9	118.19 (19)
O1—C2—C3	124.38 (17)	C11—C10—H10	120.9
O1—C2—C1	117.54 (17)	C9—C10—H10	120.9
C3—C2—C1	118.08 (17)	C12—C11—C10	120.46 (19)
C4—C3—C2	118.33 (17)	C12—C11—H11	119.8
C4—C3—H3	120.8	C10—C11—H11	119.8
C2—C3—H3	120.8	C11—C12—C7	120.76 (19)
C5—C4—C3	120.66 (18)	C11—C12—H12	119.6
C5—C4—H4	119.7	C7—C12—H12	119.6
O2—Zn—N1—C1	−168.19 (13)	Zn—O2—C6—C7	−172.72 (13)
O2i—Zn—N1—C1	−35.82 (15)	O3—C6—C7—C12	−11.6 (3)
N1i—Zn—N1—C1	82.92 (14)	O2—C6—C7—C12	166.42 (19)
O2—Zn—N1—C5	3.54 (18)	O3—C6—C7—C8	171.9 (2)
O2i—Zn—N1—C5	135.91 (16)	O2—C6—C7—C8	−10.1 (3)
N1i—Zn—N1—C5	−105.36 (17)	C12—C7—C8—C9	−0.9 (3)
O2i—Zn—O2—C6	−63.65 (13)	C6—C7—C8—C9	175.64 (17)
N1—Zn—O2—C6	58.89 (15)	C7—C8—C9—C10	0.1 (3)
N1i—Zn—O2—C6	167.73 (14)	C7—C8—C9—N2	−178.86 (17)
C5—N1—C1—C2	−1.9 (3)	O4—N2—C9—C8	0.0 (3)
Zn—N1—C1—C2	170.31 (15)	O5—N2—C9—C8	179.42 (18)
N1—C1—C2—O1	−179.81 (18)	O4—N2—C9—C10	−179.00 (19)
N1—C1—C2—C3	0.2 (3)	O5—N2—C9—C10	0.4 (3)
O1—C2—C3—C4	−178.31 (19)	C8—C9—C10—C11	0.6 (3)
C1—C2—C3—C4	1.7 (3)	N2—C9—C10—C11	179.55 (19)
C2—C3—C4—C5	−1.9 (3)	C9—C10—C11—C12	−0.5 (3)
C1—N1—C5—C4	1.8 (3)	C10—C11—C12—C7	−0.3 (3)
Zn—N1—C5—C4	−169.79 (15)	C8—C7—C12—C11	1.0 (3)
C3—C4—C5—N1	0.1 (3)	C6—C7—C12—C11	−175.53 (19)
Zn—O2—C6—O3	5.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3ii	0.91	1.73	2.642 (2)	174

Table 1

Selected bond lengths (Å)

Zn—N1	2.0486 (16)
Zn—O2	1.9527 (13)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O3i	0.91	1.73	2.642 (2)	174

Symmetry code: (i) .