{2,2′-[1,2-Phenyl­enebis(nitrilo­methyl­idyne)]diphenolato-κ4O,N,N′,O′}(pyridine-κN)zinc(II)

Eltayeb, N.E.; Teoh, S.G.; Ng, S.-L.; Fun, H.-K.; Ibrahim, K.

doi:10.1107/S1600536807017618

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{2,2′-[1,2-Phenylenebis(nitrilomethylidyne)]diphenolato-κ⁴O,N,N′,O′}(pyridine-κN)zinc(II)

N. E. Eltayeb, S. G. Teoh, S.-L. Ng, H.-K. Fun and K. Ibrahim

In the title compound, [Zn(C₂₀H₁₄N₂O₂)(C₅H₅N)], the Zn^II atom is in a distorted square-pyramidal environment. In the crystal structure, intermolecular C—H

O interactions interconnect the molecules into wave-like chains along the c axis. In addition, the crystal packing is further stabilized by weak C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017618/ng2249sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017618/ng2249Isup2.hkl Contains datablock I

CCDC reference: 646602

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Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.045
wR factor = 0.104
Data-to-parameter ratio = 40.8

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           40.00
           From the CIF: _reflns_number_total              11416
           Count of symmetry unique reflns         6282
           Completeness (_total/calc)            181.73%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      5134
           Fraction of Friedel pairs measured     0.817
           Are heavy atom types Z>Si present        yes

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

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


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Alert level A
PUBL023_ALERT_1_A There is a mismatched ^ on line 93
              \k^4^2^O,N,N',O']bis(pyridine-\kN)zinc(II)
              If you require a ^ then it should be escaped
              with a \, i.e. \^
              Otherwise there must be a matching closing ~, e.g. ^12^C
PUBL023_ALERT_1_A There is a mismatched ^ on line 274
              \k^4^2^O,N,N',O']bis(pyridine-\kN)zinc(II)
              If you require a ^ then it should be escaped
              with a \, i.e. \^
              Otherwise there must be a matching closing ~, e.g. ^12^C

   2 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

Comment top

Zinc, an element of strong interest in biology, medicine, materials and catalysis, plays important roles in various biological systems, such as neurotransmission, signal transduction and gene expression (Assaf & Chung, 1984; Berg & Shi, 1996). It is well known that zinc complexes with Schiff bases show very good activity against the leukaemic cell (Tarafder et al., 2002). Here, we report the crystal structure of the title Zn^II complex, (I), with the 2,2'-{1,2-phenylenebis[nitrilomethylylide]}diphenol Schiff base.

The Zn^II atom in (I) is five-coordinated by two O atoms and two N atoms in the basal plane, together with the N atom of the pyridine ring in the apical position, giving a distorted square-pyramidal geometry (Fig. 1 and Table 1). The Zn^II ion is displaced from the basal plane (N1/N2/O2/O1) by 0.3975 (2) Å. The N3/C21–C25 pyridine ring is attached axially to Zn1 with the torsion angle O1—Zn1—N3—C25 = -3.93 (15)°. The bond lengths and angles in (I) have normal values (Allen et al., 1987).

An intramolecular C25—H25A···O1 interaction (Table 2 and Fig. 1) generates S(5) ring motifs (Bernstein et al., 1995). In the crystal structure, the molecules are linked by intermolecular C23—H23A···O2 interactions into wave-like chains along the c axis (Fig. 2). In addition, the crystal packing is further stabilized by weak intermolecular C—H···π interactions involving the Zn1/O1/C1/C6/C7/N1 ring (centroid Cg1) (Table 2).

Related literature top

For related literature, see: Allen et al. (1987); Assaf & Chung (1984); Berg & Shi (1996); Bernstein et al. (1995); Tarafder et al. (2002).

Experimental top

The title compound was synthesized as follows. To a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol (20 ml) was added 2-hydroxybenzaldehyde (0.4 ml, 4 mmol). The mixture was refluxed with stirring for half an hour. Zinc chloride (0.272 g, 2 mmol) in ethanol (10 ml) was then added, followed by triethylamine (0.5 ml, 3.6 mmol). The mixture was stirred at

room temperature for 2 h, following which the yellow precipitate obtained was washed with ethanol (about 5 ml), dried and then washed in a copious amount of diethyl ether. This precipitate was dissolved in pyridine (15 ml), and after 9 d of slow evaporation of the pyridine at room temperature, yellow crystals of

(I) suitable for X-ray diffraction analysis were formed.

Structure description top

For related literature, see: Allen et al. (1987); Assaf & Chung (1984); Berg & Shi (1996); Bernstein et al. (1995); Tarafder et al. (2002).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atomic numbering. The dashed line indicates the intramolecular hydrogen bond.
	Fig. 2. The crystal packing of (I), viewed down the a axis. The intermolecular C—H···O hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

[2,2'-{1,2-Phenylenebis(nitrilomethylylidyne)}diphenolato- κ⁴O,N,N',O'](pyridine-κN)zinc(II) top

Crystal data top

[Zn(C₂₀H₁₄N₂O₂)(C₅H₅N)]	F(000) = 944
M_r = 458.80	D_x = 1.505 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 9040 reflections
a = 17.8611 (3) Å	θ = 2.1–40.0°
b = 11.9929 (3) Å	µ = 1.24 mm⁻¹
c = 9.4946 (2) Å	T = 100 K
β = 95.540 (1)°	Block, yellow
V = 2024.30 (7) Å³	0.53 × 0.38 × 0.21 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	11416 independent reflections
Radiation source: fine-focus sealed tube	9121 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 8.33 pixels mm^-1	θ_max = 40.0°, θ_min = 2.1°
ω scans	h = −31→31
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −19→21
T_min = 0.588, T_max = 0.778	l = −17→16
31548 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.104	w = 1/[σ²(F_o²) + 1.0902P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
11416 reflections	Δρ_max = 0.87 e Å⁻³
280 parameters	Δρ_min = −0.92 e Å⁻³
2 restraints	Absolute structure: Flack (1983), with 5258 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.014 (7)

Crystal data top

[Zn(C₂₀H₁₄N₂O₂)(C₅H₅N)]	V = 2024.30 (7) Å³
M_r = 458.80	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 17.8611 (3) Å	µ = 1.24 mm⁻¹
b = 11.9929 (3) Å	T = 100 K
c = 9.4946 (2) Å	0.53 × 0.38 × 0.21 mm
β = 95.540 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	11416 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	9121 reflections with I > 2σ(I)
T_min = 0.588, T_max = 0.778	R_int = 0.047
31548 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.104	Δρ_max = 0.87 e Å⁻³
S = 1.07	Δρ_min = −0.92 e Å⁻³
11416 reflections	Absolute structure: Flack (1983), with 5258 Friedel pairs
280 parameters	Absolute structure parameter: 0.014 (7)
2 restraints

Special details top

Experimental. The data were collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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.

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

	x	y	z	U_iso*/U_eq
Zn1	0.137941 (15)	0.276624 (17)	0.931457 (18)	0.01513 (4)
O1	0.05548 (8)	0.26576 (14)	1.05451 (15)	0.0210 (3)
O2	0.22018 (8)	0.28305 (14)	1.08423 (15)	0.0213 (3)
N1	0.06264 (9)	0.35148 (15)	0.77673 (16)	0.0166 (3)
N2	0.21070 (8)	0.35007 (15)	0.79573 (15)	0.0161 (3)
C1	−0.01125 (10)	0.30971 (18)	1.04053 (19)	0.0178 (3)
C2	−0.05900 (11)	0.29339 (19)	1.1504 (2)	0.0212 (4)
H2A	−0.0418	0.2502	1.2282	0.025*
C3	−0.12951 (11)	0.3392 (2)	1.1455 (2)	0.0245 (4)
H3A	−0.1587	0.3273	1.2200	0.029*
C4	−0.15823 (12)	0.4040 (2)	1.0294 (2)	0.0258 (4)
H4A	−0.2060	0.4353	1.0265	0.031*
C5	−0.11409 (12)	0.4202 (2)	0.9195 (2)	0.0224 (4)
H5A	−0.1328	0.4630	0.8423	0.027*
C6	−0.04126 (12)	0.3736 (2)	0.9211 (2)	0.0176 (4)
C7	−0.00347 (10)	0.39031 (18)	0.79527 (19)	0.0180 (3)
H7A	−0.0282	0.4318	0.7223	0.022*
C8	0.09499 (10)	0.36759 (17)	0.64817 (18)	0.0167 (3)
C9	0.05405 (11)	0.37665 (18)	0.51553 (19)	0.0189 (3)
H9A	0.0018	0.3751	0.5079	0.023*
C10	0.09183 (12)	0.38795 (18)	0.3952 (2)	0.0197 (3)
H10A	0.0646	0.3950	0.3071	0.024*
C11	0.17024 (12)	0.38874 (18)	0.4054 (2)	0.0200 (3)
H11A	0.1950	0.3963	0.3240	0.024*
C12	0.21155 (11)	0.37828 (18)	0.53604 (19)	0.0190 (3)
H12A	0.2638	0.3784	0.5423	0.023*
C13	0.17443 (10)	0.36752 (16)	0.65840 (17)	0.0157 (3)
C14	0.27789 (10)	0.38710 (17)	0.83114 (18)	0.0174 (3)
H14A	0.3015	0.4257	0.7629	0.021*
C15	0.31893 (12)	0.3730 (2)	0.9683 (2)	0.0175 (4)
C16	0.39295 (12)	0.4161 (2)	0.9850 (2)	0.0232 (4)
H16A	0.4121	0.4504	0.9084	0.028*
C17	0.43724 (12)	0.4087 (2)	1.1108 (2)	0.0246 (4)
H17A	0.4859	0.4373	1.1193	0.030*
C18	0.40826 (11)	0.35744 (19)	1.2266 (2)	0.0207 (3)
H18A	0.4380	0.3516	1.3123	0.025*
C19	0.33618 (11)	0.31565 (19)	1.21453 (19)	0.0201 (3)
H19A	0.3183	0.2822	1.2930	0.024*
C20	0.28810 (10)	0.32175 (17)	1.08643 (18)	0.0172 (3)
N3	0.13875 (8)	0.11047 (15)	0.86487 (16)	0.0172 (3)
C21	0.18650 (11)	0.07344 (18)	0.7742 (2)	0.0197 (3)
H21A	0.2177	0.1247	0.7351	0.024*
C22	0.19123 (11)	−0.03757 (19)	0.7364 (2)	0.0218 (3)
H22A	0.2259	−0.0603	0.6752	0.026*
C23	0.14410 (12)	−0.11397 (18)	0.7905 (2)	0.0213 (3)
H23A	0.1456	−0.1888	0.7653	0.026*
C24	0.09411 (12)	−0.0766 (2)	0.8840 (2)	0.0230 (4)
H24A	0.0619	−0.1263	0.9231	0.028*
C25	0.09292 (11)	0.03505 (19)	0.9177 (2)	0.0201 (3)
H25A	0.0591	0.0595	0.9796	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.01612 (7)	0.01586 (9)	0.01368 (7)	0.00019 (10)	0.00283 (5)	0.00089 (9)
O1	0.0196 (6)	0.0259 (8)	0.0182 (6)	0.0050 (5)	0.0054 (5)	0.0034 (5)
O2	0.0199 (6)	0.0276 (8)	0.0164 (5)	−0.0057 (5)	0.0021 (4)	0.0040 (5)
N1	0.0186 (6)	0.0166 (8)	0.0149 (6)	−0.0004 (5)	0.0034 (5)	0.0002 (5)
N2	0.0184 (6)	0.0164 (7)	0.0134 (6)	−0.0002 (5)	0.0017 (4)	0.0011 (5)
C1	0.0175 (7)	0.0189 (9)	0.0174 (7)	−0.0007 (6)	0.0035 (5)	−0.0024 (6)
C2	0.0207 (8)	0.0237 (10)	0.0197 (7)	−0.0006 (7)	0.0040 (6)	−0.0008 (7)
C3	0.0212 (8)	0.0305 (12)	0.0228 (8)	−0.0017 (7)	0.0073 (6)	−0.0043 (8)
C4	0.0187 (8)	0.0315 (12)	0.0278 (9)	0.0040 (7)	0.0049 (7)	−0.0042 (8)
C5	0.0192 (8)	0.0251 (11)	0.0229 (9)	0.0024 (7)	0.0016 (7)	−0.0014 (8)
C6	0.0171 (8)	0.0171 (9)	0.0189 (8)	−0.0002 (6)	0.0025 (6)	−0.0029 (7)
C7	0.0192 (7)	0.0178 (9)	0.0169 (7)	0.0003 (6)	0.0012 (6)	0.0003 (6)
C8	0.0204 (7)	0.0148 (8)	0.0147 (7)	0.0003 (6)	0.0013 (5)	0.0002 (6)
C9	0.0218 (8)	0.0180 (9)	0.0164 (7)	0.0023 (6)	−0.0004 (6)	0.0000 (6)
C10	0.0289 (9)	0.0161 (9)	0.0140 (7)	0.0012 (7)	0.0012 (6)	0.0013 (6)
C11	0.0299 (9)	0.0172 (9)	0.0131 (7)	0.0001 (7)	0.0030 (6)	0.0010 (6)
C12	0.0233 (8)	0.0182 (9)	0.0164 (7)	−0.0006 (6)	0.0057 (6)	0.0026 (6)
C13	0.0190 (7)	0.0145 (8)	0.0138 (6)	−0.0011 (6)	0.0026 (5)	0.0008 (5)
C14	0.0196 (7)	0.0179 (9)	0.0153 (7)	−0.0011 (6)	0.0043 (5)	0.0019 (6)
C15	0.0192 (8)	0.0180 (10)	0.0154 (7)	−0.0004 (7)	0.0016 (6)	0.0025 (6)
C16	0.0202 (8)	0.0297 (12)	0.0196 (8)	−0.0042 (7)	0.0010 (7)	0.0049 (8)
C17	0.0198 (8)	0.0306 (12)	0.0228 (8)	−0.0050 (7)	−0.0005 (6)	0.0050 (8)
C18	0.0215 (8)	0.0213 (10)	0.0186 (7)	0.0003 (7)	−0.0018 (6)	0.0016 (7)
C19	0.0218 (8)	0.0216 (10)	0.0166 (7)	−0.0018 (7)	0.0012 (6)	0.0025 (7)
C20	0.0203 (7)	0.0162 (9)	0.0150 (7)	−0.0005 (6)	0.0020 (5)	0.0004 (6)
N3	0.0151 (6)	0.0192 (8)	0.0174 (6)	−0.0001 (5)	0.0023 (5)	0.0010 (5)
C21	0.0201 (7)	0.0184 (9)	0.0213 (8)	−0.0015 (6)	0.0059 (6)	−0.0017 (7)
C22	0.0239 (8)	0.0214 (10)	0.0208 (8)	0.0011 (7)	0.0059 (6)	−0.0013 (7)
C23	0.0292 (9)	0.0160 (9)	0.0187 (7)	−0.0009 (7)	0.0020 (6)	−0.0022 (6)
C24	0.0262 (9)	0.0214 (10)	0.0222 (8)	−0.0056 (7)	0.0062 (7)	−0.0007 (7)
C25	0.0204 (8)	0.0217 (10)	0.0188 (7)	−0.0025 (6)	0.0052 (6)	0.0003 (7)

Geometric parameters (Å, º) top

Zn1—O2	1.9637 (14)	C10—H10A	0.9300
Zn1—O1	1.9707 (14)	C11—C12	1.387 (3)
Zn1—N3	2.0910 (18)	C11—H11A	0.9300
Zn1—N1	2.0956 (16)	C12—C13	1.398 (2)
Zn1—N2	2.1092 (15)	C12—H12A	0.9300
O1—C1	1.298 (2)	C14—C15	1.441 (3)
O2—C20	1.297 (2)	C14—H14A	0.9300
N1—C7	1.297 (2)	C15—C16	1.414 (3)
N1—C8	1.413 (2)	C15—C20	1.435 (3)
N2—C14	1.293 (2)	C16—C17	1.371 (3)
N2—C13	1.414 (2)	C16—H16A	0.9300
C1—C2	1.423 (3)	C17—C18	1.402 (3)
C1—C6	1.429 (3)	C17—H17A	0.9300
C2—C3	1.371 (3)	C18—C19	1.376 (3)
C2—H2A	0.9300	C18—H18A	0.9300
C3—C4	1.405 (3)	C19—C20	1.421 (3)
C3—H3A	0.9300	C19—H19A	0.9300
C4—C5	1.380 (3)	N3—C21	1.345 (2)
C4—H4A	0.9300	N3—C25	1.349 (3)
C5—C6	1.414 (3)	C21—C22	1.383 (3)
C5—H5A	0.9300	C21—H21A	0.9300
C6—C7	1.442 (3)	C22—C23	1.377 (3)
C7—H7A	0.9300	C22—H22A	0.9300
C8—C9	1.398 (3)	C23—C24	1.392 (3)
C8—C13	1.413 (2)	C23—H23A	0.9300
C9—C10	1.388 (3)	C24—C25	1.377 (3)
C9—H9A	0.9300	C24—H24A	0.9300
C10—C11	1.395 (3)	C25—H25A	0.9300

O2—Zn1—O1	96.51 (6)	C12—C11—C10	120.33 (18)
O2—Zn1—N3	103.55 (7)	C12—C11—H11A	119.8
O1—Zn1—N3	98.26 (6)	C10—C11—H11A	119.8
O2—Zn1—N1	152.21 (7)	C11—C12—C13	119.86 (18)
O1—Zn1—N1	88.75 (6)	C11—C12—H12A	120.1
N3—Zn1—N1	102.65 (6)	C13—C12—H12A	120.1
O2—Zn1—N2	88.50 (6)	C12—C13—C8	119.77 (16)
O1—Zn1—N2	158.38 (7)	C12—C13—N2	124.61 (16)
N3—Zn1—N2	100.99 (6)	C8—C13—N2	115.54 (14)
N1—Zn1—N2	77.55 (6)	N2—C14—C15	124.96 (17)
C1—O1—Zn1	130.08 (13)	N2—C14—H14A	117.5
C20—O2—Zn1	131.12 (12)	C15—C14—H14A	117.5
C7—N1—C8	121.44 (16)	C16—C15—C20	119.59 (18)
C7—N1—Zn1	126.14 (12)	C16—C15—C14	116.58 (18)
C8—N1—Zn1	112.07 (12)	C20—C15—C14	123.80 (19)
C14—N2—C13	121.32 (15)	C17—C16—C15	121.96 (19)
C14—N2—Zn1	126.56 (12)	C17—C16—H16A	119.0
C13—N2—Zn1	111.75 (11)	C15—C16—H16A	119.0
O1—C1—C2	118.57 (18)	C16—C17—C18	119.09 (19)
O1—C1—C6	124.69 (17)	C16—C17—H17A	120.5
C2—C1—C6	116.73 (18)	C18—C17—H17A	120.5
C3—C2—C1	122.2 (2)	C19—C18—C17	120.51 (18)
C3—C2—H2A	118.9	C19—C18—H18A	119.7
C1—C2—H2A	118.9	C17—C18—H18A	119.7
C2—C3—C4	120.89 (18)	C18—C19—C20	122.40 (17)
C2—C3—H3A	119.6	C18—C19—H19A	118.8
C4—C3—H3A	119.6	C20—C19—H19A	118.8
C5—C4—C3	118.62 (19)	O2—C20—C19	118.83 (16)
C5—C4—H4A	120.7	O2—C20—C15	124.72 (17)
C3—C4—H4A	120.7	C19—C20—C15	116.44 (17)
C4—C5—C6	121.9 (2)	C21—N3—C25	117.51 (18)
C4—C5—H5A	119.1	C21—N3—Zn1	122.12 (14)
C6—C5—H5A	119.1	C25—N3—Zn1	120.30 (13)
C5—C6—C1	119.63 (18)	N3—C21—C22	122.83 (19)
C5—C6—C7	116.1 (2)	N3—C21—H21A	118.6
C1—C6—C7	124.18 (18)	C22—C21—H21A	118.6
N1—C7—C6	124.60 (18)	C23—C22—C21	119.27 (18)
N1—C7—H7A	117.7	C23—C22—H22A	120.4
C6—C7—H7A	117.7	C21—C22—H22A	120.4
C9—C8—C13	119.77 (16)	C22—C23—C24	118.4 (2)
C9—C8—N1	124.52 (16)	C22—C23—H23A	120.8
C13—C8—N1	115.61 (15)	C24—C23—H23A	120.8
C10—C9—C8	119.68 (18)	C25—C24—C23	119.12 (19)
C10—C9—H9A	120.2	C25—C24—H24A	120.4
C8—C9—H9A	120.2	C23—C24—H24A	120.4
C9—C10—C11	120.59 (19)	N3—C25—C24	122.81 (17)
C9—C10—H10A	119.7	N3—C25—H25A	118.6
C11—C10—H10A	119.7	C24—C25—H25A	118.6

O2—Zn1—O1—C1	142.18 (19)	C8—C9—C10—C11	0.9 (3)
N3—Zn1—O1—C1	−113.06 (19)	C9—C10—C11—C12	0.0 (3)
N1—Zn1—O1—C1	−10.46 (19)	C10—C11—C12—C13	−0.4 (3)
N2—Zn1—O1—C1	39.7 (3)	C11—C12—C13—C8	−0.1 (3)
O1—Zn1—O2—C20	−157.39 (19)	C11—C12—C13—N2	176.26 (19)
N3—Zn1—O2—C20	102.47 (19)	C9—C8—C13—C12	1.0 (3)
N1—Zn1—O2—C20	−57.7 (3)	N1—C8—C13—C12	177.39 (18)
N2—Zn1—O2—C20	1.53 (19)	C9—C8—C13—N2	−175.69 (18)
O2—Zn1—N1—C7	−88.4 (2)	N1—C8—C13—N2	0.7 (3)
O1—Zn1—N1—C7	13.18 (18)	C14—N2—C13—C12	29.3 (3)
N3—Zn1—N1—C7	111.36 (18)	Zn1—N2—C13—C12	−157.32 (16)
N2—Zn1—N1—C7	−149.98 (19)	C14—N2—C13—C8	−154.23 (19)
O2—Zn1—N1—C8	84.83 (18)	Zn1—N2—C13—C8	19.2 (2)
O1—Zn1—N1—C8	−173.55 (13)	C13—N2—C14—C15	−180.0 (2)
N3—Zn1—N1—C8	−75.36 (14)	Zn1—N2—C14—C15	7.7 (3)
N2—Zn1—N1—C8	23.29 (13)	N2—C14—C15—C16	177.8 (2)
O2—Zn1—N2—C14	−5.67 (18)	N2—C14—C15—C20	−4.2 (4)
O1—Zn1—N2—C14	98.3 (2)	C20—C15—C16—C17	1.2 (4)
N3—Zn1—N2—C14	−109.17 (18)	C14—C15—C16—C17	179.4 (2)
N1—Zn1—N2—C14	150.13 (19)	C15—C16—C17—C18	−0.3 (4)
O2—Zn1—N2—C13	−178.67 (14)	C16—C17—C18—C19	−0.4 (4)
O1—Zn1—N2—C13	−74.7 (2)	C17—C18—C19—C20	0.2 (3)
N3—Zn1—N2—C13	77.82 (13)	Zn1—O2—C20—C19	179.71 (15)
N1—Zn1—N2—C13	−22.88 (13)	Zn1—O2—C20—C15	0.8 (3)
Zn1—O1—C1—C2	−176.48 (15)	C18—C19—C20—O2	−178.2 (2)
Zn1—O1—C1—C6	4.0 (3)	C18—C19—C20—C15	0.7 (3)
O1—C1—C2—C3	178.4 (2)	C16—C15—C20—O2	177.5 (2)
C6—C1—C2—C3	−2.0 (3)	C14—C15—C20—O2	−0.5 (4)
C1—C2—C3—C4	0.8 (4)	C16—C15—C20—C19	−1.4 (3)
C2—C3—C4—C5	0.3 (4)	C14—C15—C20—C19	−179.4 (2)
C3—C4—C5—C6	0.0 (4)	O2—Zn1—N3—C21	−82.04 (15)
C4—C5—C6—C1	−1.3 (4)	O1—Zn1—N3—C21	179.17 (15)
C4—C5—C6—C7	175.6 (2)	N1—Zn1—N3—C21	88.61 (15)
O1—C1—C6—C5	−178.2 (2)	N2—Zn1—N3—C21	9.07 (16)
C2—C1—C6—C5	2.3 (3)	O2—Zn1—N3—C25	94.86 (15)
O1—C1—C6—C7	5.1 (4)	O1—Zn1—N3—C25	−3.93 (15)
C2—C1—C6—C7	−174.4 (2)	N1—Zn1—N3—C25	−94.50 (15)
C8—N1—C7—C6	177.53 (19)	N2—Zn1—N3—C25	−174.04 (14)
Zn1—N1—C7—C6	−9.8 (3)	C25—N3—C21—C22	−1.4 (3)
C5—C6—C7—N1	−178.3 (2)	Zn1—N3—C21—C22	175.55 (16)
C1—C6—C7—N1	−1.5 (4)	N3—C21—C22—C23	1.6 (3)
C7—N1—C8—C9	−30.6 (3)	C21—C22—C23—C24	−1.2 (3)
Zn1—N1—C8—C9	155.77 (17)	C22—C23—C24—C25	0.7 (3)
C7—N1—C8—C13	153.21 (19)	C21—N3—C25—C24	0.9 (3)
Zn1—N1—C8—C13	−20.4 (2)	Zn1—N3—C25—C24	−176.16 (16)
C13—C8—C9—C10	−1.4 (3)	C23—C24—C25—N3	−0.5 (3)
N1—C8—C9—C10	−177.44 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25A···O1	0.93	2.58	3.156 (3)	121
C23—H23A···O2ⁱ	0.93	2.54	3.211 (3)	129
C18—H18A···Cg1ⁱⁱ	0.93	2.87	3.537 (2)	130

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

Experimental details

Crystal data
Chemical formula	[Zn(C₂₀H₁₄N₂O₂)(C₅H₅N)]
M_r	458.80
Crystal system, space group	Monoclinic, Cc
Temperature (K)	100
a, b, c (Å)	17.8611 (3), 11.9929 (3), 9.4946 (2)
β (°)	95.540 (1)
V (Å³)	2024.30 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.24
Crystal size (mm)	0.53 × 0.38 × 0.21

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.588, 0.778
No. of measured, independent and observed [I > 2σ(I)] reflections	31548, 11416, 9121
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.904

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.104, 1.07
No. of reflections	11416
No. of parameters	280
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.87, −0.92
Absolute structure	Flack (1983), with 5258 Friedel pairs
Absolute structure parameter	0.014 (7)

Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

Zn1—O2	1.9637 (14)	Zn1—N1	2.0956 (16)
Zn1—O1	1.9707 (14)	Zn1—N2	2.1092 (15)
Zn1—N3	2.0910 (18)

O2—Zn1—O1	96.51 (6)	N3—Zn1—N1	102.65 (6)
O2—Zn1—N3	103.55 (7)	O2—Zn1—N2	88.50 (6)
O1—Zn1—N3	98.26 (6)	O1—Zn1—N2	158.38 (7)
O2—Zn1—N1	152.21 (7)	N3—Zn1—N2	100.99 (6)
O1—Zn1—N1	88.75 (6)	N1—Zn1—N2	77.55 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C25—H25A···O1	0.93	2.58	3.156 (3)	121
C23—H23A···O2ⁱ	0.93	2.54	3.211 (3)	129
C18—H18A···Cg1ⁱⁱ	0.93	2.87	3.537 (2)	130

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

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