Bis(4-methoxy­benzaldehyde 2-hydroxy­benzoyl­hydrazonato)pyridine­zinc(II) pyridine solvate

Tai, X.-S.; Yin, J.; Hao, M.-Y.

doi:10.1107/S1600536807028917

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Bis(4-methoxybenzaldehyde 2-hydroxybenzoylhydrazonato)pyridinezinc(II) pyridine solvate

X.-S. Tai, J. Yin and M.-Y. Hao

In the title compound, [Zn(C₁₅H₁₃N₂O₃)₂(C₅H₅N)]·C₅H₅N, a distorted ZnN₃O₂ trigonal–bipyramidal coordination geometry results from the coordination of the two bidentate ligands and one pyridine molecule. A crystallographic twofold rotation axis passes through Zn and the pyridine ligand. The pyridine solvent molecule is disordered over an inversion centre. Intermolecular C—H

O and intramolecular C—H

O and O—H

N hydrogen-bonding interactions help to establish the crystal packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028917/at2306sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028917/at2306Isup2.hkl Contains datablock I

CCDC reference: 654776

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.007 Å
Disorder in solvent or counterion
R factor = 0.044
wR factor = 0.144
Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C19
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      21.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C19    -   C20    ...       1.34 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

As part of our onging studies of metal coordination complexes with multidentate ligands (Tai et al., 2005), the synthesis and structure of the title compound, (I), is reported.

Two N,O-bidentate ligands and one pyridine molecule are attached to the zinc atom, resulting in a distorted ZnN₃O₂ trigonal bipyramidal co-ordination geometry (Fig. 1). The C1═O1 [1.287 (4) Å] and C8═N2 [1.290 (5) Å] bond lengths implies double bond character. The dihedral angle between the (C2—C7) and (C9—C14) planes is 29.0 (2)°. The geometrical parameters for (I) are normal.

Two molecules of pyridine complete the structure of (I) and the intermolecular C—H···O, and intramolecular C—H···O and O—H···N hydrogen bonding interactions help to establish the crystal packing..

Related literature top

For related literature, see: Tai et al. (2005).

Experimental top

1 mmol of Zinc acetate was added to a solution of nisoldehyde-salicyloyl hydrazone (2 mmol) in 10 ml of CH₃OH/pyridine (v/v 10:1). The mixture was continuously stirred for 6 h at refluxing temperature, evaporating some solvent, then, upon cooling, the solid product was collected by filtration and dried in vacuo (yield 58%). Clear blocks of (I) were obtained by evaporation from a methanol solution after two week.

Structure description top

As part of our onging studies of metal coordination complexes with multidentate ligands (Tai et al., 2005), the synthesis and structure of the title compound, (I), is reported.

For related literature, see: Tai et al. (2005).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The complex molecule in (I), with 50% probabiility ellipsoids.

Bis(4-methoxybenzaldehyde 2-hydroxybenzoylhydrazonato)pyridinezinc(II) pyridine solvate top

Crystal data top

[Zn(C₁₅H₁₃N₂O₃)₂(C₅H₅N)]·C₅H₅N	F(000) = 1584
M_r = 762.14	D_x = 1.387 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 1992 reflections
a = 15.447 (2) Å	θ = 2.4–23.0°
b = 10.0122 (17) Å	µ = 0.73 mm⁻¹
c = 23.598 (3) Å	T = 298 K
V = 3649.6 (9) Å³	Laminar, colourless
Z = 4	0.43 × 0.32 × 0.19 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3183 independent reflections
Radiation source: fine-focus sealed tube	1794 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
φ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −18→16
T_min = 0.744, T_max = 0.874	k = −10→11
14274 measured reflections	l = −27→27

Refinement top

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0568P)² + 2.7233P] where P = (F_o² + 2F_c²)/3
3183 reflections	(Δ/σ)_max < 0.001
241 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Zn(C₁₅H₁₃N₂O₃)₂(C₅H₅N)]·C₅H₅N	V = 3649.6 (9) Å³
M_r = 762.14	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 15.447 (2) Å	µ = 0.73 mm⁻¹
b = 10.0122 (17) Å	T = 298 K
c = 23.598 (3) Å	0.43 × 0.32 × 0.19 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3183 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1794 reflections with I > 2σ(I)
T_min = 0.744, T_max = 0.874	R_int = 0.068
14274 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.144	H-atom parameters constrained
S = 1.06	Δρ_max = 0.30 e Å⁻³
3183 reflections	Δρ_min = −0.41 e Å⁻³
241 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Zn1	0.00000	0.36156 (7)	0.25000	0.0450 (3)
O1	0.01587 (16)	0.2491 (3)	0.18135 (13)	0.0527 (10)
O2	0.26418 (18)	0.0842 (3)	0.15935 (14)	0.0655 (11)
O3	0.2533 (2)	0.7767 (3)	0.43932 (15)	0.0750 (14)
N1	0.1609 (2)	0.2463 (3)	0.20545 (15)	0.0461 (13)
N2	0.14146 (19)	0.3425 (3)	0.24685 (15)	0.0411 (11)
N3	0.00000	0.5678 (5)	0.25000	0.0460 (16)
C1	0.0935 (2)	0.2040 (4)	0.17617 (18)	0.0393 (14)
C2	0.1130 (2)	0.0966 (4)	0.13529 (18)	0.0403 (14)
C3	0.1957 (3)	0.0397 (4)	0.13005 (19)	0.0443 (16)
C4	0.2087 (3)	−0.0664 (5)	0.0931 (2)	0.0567 (17)
C5	0.1428 (3)	−0.1155 (5)	0.0603 (2)	0.069 (2)
C6	0.0614 (3)	−0.0602 (5)	0.0644 (2)	0.072 (2)
C7	0.0471 (3)	0.0440 (5)	0.1016 (2)	0.0597 (18)
C8	0.2098 (3)	0.3930 (4)	0.26981 (19)	0.0500 (16)
C9	0.2142 (3)	0.4902 (4)	0.31474 (19)	0.0463 (16)
C10	0.2943 (3)	0.5537 (4)	0.3236 (2)	0.0540 (17)
C11	0.3043 (3)	0.6484 (5)	0.3644 (2)	0.0600 (19)
C12	0.2361 (3)	0.6831 (4)	0.3983 (2)	0.0530 (17)
C13	0.1564 (3)	0.6219 (5)	0.3912 (2)	0.0570 (17)
C14	0.1464 (3)	0.5250 (5)	0.34936 (19)	0.0543 (16)
C15	0.1843 (4)	0.8321 (6)	0.4695 (3)	0.097 (3)
C16	0.0500 (3)	0.6355 (5)	0.2142 (2)	0.0570 (18)
C17	0.0512 (3)	0.7726 (5)	0.2125 (2)	0.071 (2)
C18	0.00000	0.8425 (7)	0.25000	0.082 (3)
N4	0.0692 (4)	0.5482 (7)	0.0272 (3)	0.107 (3)	0.500
C19	0.0303 (4)	0.4354 (6)	0.0459 (3)	0.084 (3)
C20	−0.0386 (4)	0.3879 (6)	0.0180 (3)	0.089 (3)
C21	0.0692 (4)	0.5482 (7)	0.0272 (3)	0.107 (3)	0.500
H2	0.24920	0.14630	0.17980	0.0980*
H4	0.26330	−0.10490	0.09050	0.0680*
H5	0.15300	−0.18580	0.03540	0.0830*
H6	0.01630	−0.09280	0.04220	0.0870*
H7	−0.00820	0.08030	0.10420	0.0720*
H8	0.26260	0.36300	0.25570	0.0600*
H10	0.34140	0.53040	0.30120	0.0650*
H11	0.35770	0.68980	0.36920	0.0720*
H13	0.10990	0.64530	0.41420	0.0690*
H14	0.09300	0.48330	0.34480	0.0650*
H15A	0.14340	0.87010	0.44350	0.1460*
H15B	0.20560	0.90060	0.49440	0.1460*
H15C	0.15650	0.76380	0.49150	0.1460*
H16	0.08540	0.58830	0.18950	0.0680*
H17	0.08600	0.81740	0.18660	0.0850*
H18	0.00000	0.93530	0.25000	0.0980*
H19	0.05130	0.39130	0.07770	0.1000*
H20	−0.06530	0.30980	0.03030	0.1070*
H21	0.11750	0.58130	0.04610	0.1290*	0.500

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0366 (4)	0.0443 (4)	0.0541 (5)	0.0000	0.0067 (4)	0.0000
O1	0.0335 (15)	0.0647 (19)	0.060 (2)	0.0082 (14)	−0.0031 (14)	−0.0111 (16)
O2	0.0406 (17)	0.074 (2)	0.082 (2)	0.0109 (15)	−0.0115 (16)	−0.0238 (19)
O3	0.068 (2)	0.078 (2)	0.079 (3)	−0.0053 (19)	−0.0110 (19)	−0.025 (2)
N1	0.0343 (18)	0.048 (2)	0.056 (3)	0.0005 (16)	0.0005 (17)	−0.0103 (19)
N2	0.0333 (17)	0.0440 (19)	0.046 (2)	−0.0009 (14)	0.0023 (17)	−0.003 (2)
N3	0.030 (2)	0.048 (3)	0.060 (3)	0.0000	0.009 (3)	0.0000
C1	0.032 (2)	0.044 (2)	0.042 (3)	0.0010 (18)	−0.0018 (19)	0.006 (2)
C2	0.036 (2)	0.041 (2)	0.044 (3)	0.0001 (18)	−0.0008 (19)	0.000 (2)
C3	0.040 (2)	0.045 (3)	0.048 (3)	0.0008 (19)	−0.001 (2)	0.000 (2)
C4	0.051 (3)	0.055 (3)	0.064 (3)	0.009 (2)	0.005 (2)	−0.009 (3)
C5	0.071 (3)	0.063 (4)	0.073 (4)	−0.001 (3)	0.006 (3)	−0.025 (3)
C6	0.056 (3)	0.077 (4)	0.083 (4)	−0.005 (3)	−0.014 (3)	−0.028 (3)
C7	0.042 (2)	0.068 (3)	0.069 (4)	0.004 (2)	−0.005 (2)	−0.013 (3)
C8	0.040 (2)	0.052 (3)	0.058 (3)	0.001 (2)	0.002 (2)	−0.005 (2)
C9	0.041 (2)	0.049 (3)	0.049 (3)	−0.002 (2)	−0.002 (2)	−0.001 (2)
C10	0.043 (3)	0.058 (3)	0.061 (3)	−0.003 (2)	0.005 (2)	−0.004 (3)
C11	0.043 (3)	0.064 (3)	0.073 (4)	−0.011 (2)	−0.001 (2)	−0.011 (3)
C12	0.056 (3)	0.046 (3)	0.057 (3)	−0.003 (2)	−0.016 (2)	−0.004 (2)
C13	0.048 (3)	0.063 (3)	0.060 (3)	0.002 (2)	0.004 (2)	−0.006 (3)
C14	0.042 (2)	0.067 (3)	0.054 (3)	−0.007 (2)	−0.001 (2)	−0.008 (3)
C15	0.094 (4)	0.105 (5)	0.093 (5)	0.018 (4)	0.000 (4)	−0.042 (4)
C16	0.041 (2)	0.057 (3)	0.073 (4)	−0.001 (2)	0.013 (2)	0.004 (3)
C17	0.055 (3)	0.064 (4)	0.094 (5)	−0.013 (3)	0.000 (3)	0.026 (3)
C18	0.070 (5)	0.042 (4)	0.134 (8)	0.0000	−0.011 (6)	0.0000
N4	0.087 (4)	0.104 (5)	0.131 (6)	−0.011 (4)	−0.016 (4)	−0.002 (5)
C19	0.091 (4)	0.070 (4)	0.090 (5)	0.005 (3)	0.004 (4)	0.014 (4)
C20	0.084 (4)	0.068 (4)	0.115 (6)	−0.022 (3)	0.009 (4)	0.016 (4)
C21	0.087 (4)	0.104 (5)	0.131 (6)	−0.011 (4)	−0.016 (4)	−0.002 (5)

Geometric parameters (Å, º) top

Zn1—O1	1.988 (3)	C9—C10	1.407 (6)
Zn1—N2	2.195 (3)	C10—C11	1.360 (7)
Zn1—N3	2.065 (5)	C11—C12	1.368 (7)
Zn1—O1ⁱ	1.988 (3)	C12—C13	1.385 (7)
Zn1—N2ⁱ	2.195 (3)	C13—C14	1.393 (7)
O1—C1	1.287 (4)	C16—C17	1.373 (7)
O2—C3	1.340 (5)	C17—C18	1.378 (6)
O3—C12	1.373 (5)	C4—H4	0.9300
O3—C15	1.397 (7)	C5—H5	0.9300
O2—H2	0.8200	C6—H6	0.9300
N1—C1	1.319 (5)	C7—H7	0.9300
N1—N2	1.404 (5)	C8—H8	0.9300
N2—C8	1.290 (5)	C10—H10	0.9300
N3—C16ⁱ	1.330 (5)	C11—H11	0.9300
N3—C16	1.330 (5)	C13—H13	0.9300
N4—C19	1.353 (9)	C14—H14	0.9300
N4—C20ⁱⁱ	1.331 (10)	C15—H15B	0.9600
N4—H21	0.9300	C15—H15C	0.9600
C1—C2	1.476 (6)	C15—H15A	0.9600
C2—C3	1.404 (6)	C16—H16	0.9300
C2—C7	1.395 (6)	C17—H17	0.9300
C3—C4	1.389 (6)	C18—H18	0.9300
C4—C5	1.370 (7)	C19—C20	1.339 (9)
C5—C6	1.377 (7)	C19—C21	1.353 (9)
C6—C7	1.381 (7)	C19—H19	0.9300
C8—C9	1.441 (6)	C20—H20	0.9300
C9—C14	1.373 (6)	C21—H21	0.9300

Zn1···C14	3.646 (5)	C13···H15C	2.7600
Zn1···C14ⁱ	3.646 (5)	C13···H15A	2.7800
Zn1···H14	2.9200	C15···H13	2.5500
Zn1···H14ⁱ	2.9200	C16···H14ⁱ	3.0200
O1···N1	2.312 (4)	C19···H15C^ix	3.0700
O1···N2	2.651 (4)	C20···H5^x	2.9700
O1···N2ⁱ	3.107 (4)	C21···H5^xi	2.9700
O2···C16ⁱⁱⁱ	3.190 (6)	H2···N1	1.8000
O2···N1	2.522 (4)	H2···C1	2.4700
O2···C8ⁱⁱⁱ	3.259 (5)	H5···C21^viii	2.9700
O1···H7	2.5100	H5···H21^viii	2.4100
O1···H19	2.8800	H5···H20^x	2.4000
O1···H11^iv	2.7800	H5···C20^x	2.9700
O2···H16ⁱⁱⁱ	2.4300	H5···O3^xii	2.8400
O3···H5^v	2.8400	H6···H15A^xiii	2.5200
O3···H20^vi	2.9100	H7···C11^iv	3.0700
N1···O1	2.312 (4)	H7···O1	2.5100
N1···O2	2.522 (4)	H7···H11^iv	2.4300
N2···O1ⁱ	3.107 (4)	H8···H10	2.3300
N2···O1	2.651 (4)	H10···H8	2.3300
N2···N3	3.142 (5)	H11···O1^vi	2.7800
N2···C1	2.292 (5)	H11···H7^vi	2.4300
N2···C16	3.346 (6)	H13···H15A	2.4100
N3···C14ⁱ	3.286 (5)	H13···C15	2.5500
N3···C14	3.286 (5)	H13···H15C	2.2900
N3···N2	3.142 (5)	H14···Zn1	2.9200
N3···N2ⁱ	3.142 (5)	H14···N2	2.8100
N1···H2	1.8000	H14···C16ⁱ	3.0200
N2···H16	2.9400	H14···N3	2.7900
N2···H14	2.8100	H15A···H6^xiv	2.5200
N3···H14	2.7900	H15A···H13	2.4100
N3···H14ⁱ	2.7900	H15A···C13	2.7800
C8···O2^vii	3.259 (5)	H15B···C4^xv	2.8600
C8···C11ⁱⁱⁱ	3.321 (6)	H15B···C5^xv	2.8300
C11···C8^vii	3.321 (6)	H15C···C13	2.7600
C14···N3	3.286 (5)	H15C···H13	2.2900
C14···C16ⁱ	3.561 (7)	H15C···C19^xv	3.0700
C14···Zn1	3.646 (5)	H16···O2^vii	2.4300
C16···C14ⁱ	3.561 (7)	H16···N2	2.9400
C16···O2^vii	3.190 (6)	H17···C2^xi	3.0700
C1···H19	3.0600	H17···C3^xi	3.1000
C1···H2	2.4700	H17···C7^xi	3.0900
C2···H17^viii	3.0700	H19···O1	2.8800
C3···H17^viii	3.1000	H19···C1	3.0600
C4···H15B^ix	2.8600	H20···H5^x	2.4000
C5···H21^viii	3.0800	H20···O3^iv	2.9100
C5···H15B^ix	2.8300	H21···C5^xi	3.0800
C7···H17^viii	3.0900	H21···H5^xi	2.4100
C11···H7^vi	3.0700

O1—Zn1—N2	78.49 (11)	C9—C14—C13	120.9 (4)
O1—Zn1—N3	124.50 (9)	N3—C16—C17	122.4 (4)
O1—Zn1—O1ⁱ	111.01 (13)	C16—C17—C18	118.8 (5)
O1—Zn1—N2ⁱ	95.80 (11)	C17—C18—C17ⁱ	119.0 (6)
N2—Zn1—N3	94.99 (8)	C5—C4—H4	119.00
O1ⁱ—Zn1—N2	95.80 (11)	C3—C4—H4	119.00
N2—Zn1—N2ⁱ	170.02 (12)	C6—C5—H5	120.00
O1ⁱ—Zn1—N3	124.50 (9)	C4—C5—H5	120.00
N2ⁱ—Zn1—N3	94.99 (8)	C7—C6—H6	120.00
O1ⁱ—Zn1—N2ⁱ	78.49 (11)	C5—C6—H6	120.00
Zn1—O1—C1	113.0 (3)	C6—C7—H7	119.00
C12—O3—C15	118.9 (4)	C2—C7—H7	119.00
C3—O2—H2	109.00	C9—C8—H8	116.00
N2—N1—C1	114.6 (3)	N2—C8—H8	116.00
Zn1—N2—N1	107.2 (2)	C9—C10—H10	119.00
Zn1—N2—C8	140.1 (3)	C11—C10—H10	119.00
N1—N2—C8	112.7 (3)	C10—C11—H11	120.00
Zn1—N3—C16ⁱ	120.6 (3)	C12—C11—H11	120.00
C16—N3—C16ⁱ	118.7 (5)	C14—C13—H13	120.00
Zn1—N3—C16	120.6 (3)	C12—C13—H13	120.00
C19—N4—C20ⁱⁱ	120.3 (6)	C13—C14—H14	120.00
C20ⁱⁱ—N4—H21	120.00	C9—C14—H14	120.00
C19—N4—H21	120.00	O3—C15—H15B	110.00
O1—C1—N1	125.0 (4)	O3—C15—H15A	110.00
N1—C1—C2	114.5 (3)	H15A—C15—H15C	109.00
O1—C1—C2	120.5 (3)	H15B—C15—H15C	109.00
C1—C2—C7	119.9 (3)	O3—C15—H15C	110.00
C1—C2—C3	122.6 (3)	H15A—C15—H15B	109.00
C3—C2—C7	117.4 (4)	N3—C16—H16	119.00
O2—C3—C4	117.7 (4)	C17—C16—H16	119.00
C2—C3—C4	119.8 (4)	C16—C17—H17	121.00
O2—C3—C2	122.5 (4)	C18—C17—H17	121.00
C3—C4—C5	121.5 (4)	C17—C18—H18	121.00
C4—C5—C6	119.6 (5)	C17ⁱ—C18—H18	121.00
C5—C6—C7	119.6 (4)	N4—C19—C20	119.3 (6)
C2—C7—C6	122.1 (4)	C20—C19—C21	119.3 (6)
N2—C8—C9	127.8 (4)	N4ⁱⁱ—C20—C19	120.4 (6)
C10—C9—C14	117.9 (4)	C19—C21—C20ⁱⁱ	120.3 (6)
C8—C9—C14	125.0 (4)	N4—C19—H19	120.00
C8—C9—C10	117.1 (4)	C20—C19—H19	120.00
C9—C10—C11	121.3 (4)	C21—C19—H19	120.00
C10—C11—C12	120.2 (4)	C19—C20—H20	120.00
O3—C12—C11	115.9 (4)	N4ⁱⁱ—C20—H20	120.00
O3—C12—C13	124.0 (4)	C19—C21—H21	120.00
C11—C12—C13	120.1 (4)	C20ⁱⁱ—C21—H21	120.00
C12—C13—C14	119.5 (4)

N2—Zn1—O1—C1	11.7 (3)	O1—C1—C2—C7	0.5 (6)
N3—Zn1—O1—C1	99.8 (3)	N1—C1—C2—C3	3.0 (6)
O1ⁱ—Zn1—O1—C1	−80.2 (3)	O1—C1—C2—C3	−176.8 (4)
N2ⁱ—Zn1—O1—C1	−160.1 (3)	C1—C2—C3—C4	176.3 (4)
O1—Zn1—N2—N1	−9.7 (2)	C7—C2—C3—O2	178.5 (4)
O1—Zn1—N2—C8	168.4 (5)	C1—C2—C3—O2	−4.1 (6)
N3—Zn1—N2—N1	−133.9 (2)	C1—C2—C7—C6	−177.3 (4)
N3—Zn1—N2—C8	44.2 (4)	C3—C2—C7—C6	0.2 (7)
O1ⁱ—Zn1—N2—N1	100.6 (2)	C7—C2—C3—C4	−1.2 (6)
O1ⁱ—Zn1—N2—C8	−81.3 (5)	C2—C3—C4—C5	1.6 (7)
O1—Zn1—N3—C16	−33.8 (2)	O2—C3—C4—C5	−178.1 (4)
O1—Zn1—N3—C16ⁱ	146.2 (2)	C3—C4—C5—C6	−0.9 (7)
N2—Zn1—N3—C16	45.6 (3)	C4—C5—C6—C7	−0.1 (7)
N2—Zn1—N3—C16ⁱ	−134.4 (3)	C5—C6—C7—C2	0.5 (7)
O1ⁱ—Zn1—N3—C16	146.2 (2)	N2—C8—C9—C14	14.9 (7)
N2ⁱ—Zn1—N3—C16	−134.4 (3)	N2—C8—C9—C10	−165.2 (4)
Zn1—O1—C1—N1	−13.0 (5)	C10—C9—C14—C13	1.2 (7)
Zn1—O1—C1—C2	166.8 (3)	C8—C9—C14—C13	−178.9 (4)
C15—O3—C12—C11	170.1 (5)	C8—C9—C10—C11	178.9 (4)
C15—O3—C12—C13	−11.8 (7)	C14—C9—C10—C11	−1.2 (7)
C1—N1—N2—Zn1	6.5 (4)	C9—C10—C11—C12	0.6 (7)
N2—N1—C1—C2	−176.2 (3)	C10—C11—C12—C13	0.0 (7)
N2—N1—C1—O1	3.6 (6)	C10—C11—C12—O3	178.1 (4)
C1—N1—N2—C8	−172.2 (4)	C11—C12—C13—C14	0.0 (7)
Zn1—N2—C8—C9	4.2 (8)	O3—C12—C13—C14	−178.0 (4)
N1—N2—C8—C9	−177.7 (4)	C12—C13—C14—C9	−0.6 (7)
C16ⁱ—N3—C16—C17	−0.7 (6)	N3—C16—C17—C18	1.3 (7)
Zn1—N3—C16—C17	179.3 (3)	C16—C17—C18—C17ⁱ	−0.6 (5)
C19—N4—C20ⁱⁱ—C19ⁱⁱ	−0.9 (10)	N4—C19—C20—N4ⁱⁱ	−0.9 (10)
C20ⁱⁱ—N4—C19—C20	0.9 (10)	C21—C19—C20—N4ⁱⁱ	−0.9 (10)
N1—C1—C2—C7	−179.7 (4)	C20—C19—C21—C20ⁱⁱ	0.9 (10)

Symmetry codes: (i) −x, y, −z+1/2; (ii) −x, −y+1, −z; (iii) −x+1/2, y−1/2, z; (iv) x−1/2, y−1/2, −z+1/2; (v) −x+1/2, −y+1/2, z+1/2; (vi) x+1/2, y+1/2, −z+1/2; (vii) −x+1/2, y+1/2, z; (viii) x, y−1, z; (ix) x, −y+1, z−1/2; (x) −x, −y, −z; (xi) x, y+1, z; (xii) −x+1/2, −y+1/2, z−1/2; (xiii) −x, y−1, −z+1/2; (xiv) −x, y+1, −z+1/2; (xv) x, −y+1, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.80	2.522 (4)	147
C7—H7···O1	0.93	2.51	2.827 (6)	100
C16—H16···O2^vii	0.93	2.43	3.190 (6)	139

Symmetry code: (vii) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	[Zn(C₁₅H₁₃N₂O₃)₂(C₅H₅N)]·C₅H₅N
M_r	762.14
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	298
a, b, c (Å)	15.447 (2), 10.0122 (17), 23.598 (3)
V (Å³)	3649.6 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.73
Crystal size (mm)	0.43 × 0.32 × 0.19

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.744, 0.874
No. of measured, independent and observed [I > 2σ(I)] reflections	14274, 3183, 1794
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.144, 1.06
No. of reflections	3183
No. of parameters	241
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.41

Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.

Selected geometric parameters (Å, º) top

Zn1—O1	1.988 (3)	O3—C15	1.397 (7)
Zn1—N2	2.195 (3)	N1—C1	1.319 (5)
Zn1—N3	2.065 (5)	N1—N2	1.404 (5)
Zn1—O1ⁱ	1.988 (3)	N2—C8	1.290 (5)
Zn1—N2ⁱ	2.195 (3)	N3—C16ⁱ	1.330 (5)
O1—C1	1.287 (4)	N3—C16	1.330 (5)
O2—C3	1.340 (5)	N4—C19	1.353 (9)
O3—C12	1.373 (5)	N4—C20ⁱⁱ	1.331 (10)

O1—Zn1—N2	78.49 (11)	Zn1—N3—C16ⁱ	120.6 (3)
O1—Zn1—N3	124.50 (9)	C16—N3—C16ⁱ	118.7 (5)
O1—Zn1—O1ⁱ	111.01 (13)	Zn1—N3—C16	120.6 (3)
O1—Zn1—N2ⁱ	95.80 (11)	C19—N4—C20ⁱⁱ	120.3 (6)
N2—Zn1—N3	94.99 (8)	O1—C1—N1	125.0 (4)
O1ⁱ—Zn1—N2	95.80 (11)	N1—C1—C2	114.5 (3)
N2—Zn1—N2ⁱ	170.02 (12)	O1—C1—C2	120.5 (3)
O1ⁱ—Zn1—N3	124.50 (9)	O2—C3—C4	117.7 (4)
N2ⁱ—Zn1—N3	94.99 (8)	O2—C3—C2	122.5 (4)
O1ⁱ—Zn1—N2ⁱ	78.49 (11)	N2—C8—C9	127.8 (4)
Zn1—O1—C1	113.0 (3)	O3—C12—C11	115.9 (4)
C12—O3—C15	118.9 (4)	O3—C12—C13	124.0 (4)
N2—N1—C1	114.6 (3)	N3—C16—C17	122.4 (4)
Zn1—N2—N1	107.2 (2)	N4—C19—C20	119.3 (6)
Zn1—N2—C8	140.1 (3)	N4ⁱⁱ—C20—C19	120.4 (6)
N1—N2—C8	112.7 (3)

Symmetry codes: (i) −x, y, −z+1/2; (ii) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1	0.82	1.80	2.522 (4)	147
C7—H7···O1	0.93	2.51	2.827 (6)	100
C16—H16···O2ⁱⁱⁱ	0.93	2.43	3.190 (6)	139

Symmetry code: (iii) −x+1/2, y+1/2, z.

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