(Ethanol-κO){4,4′,6,6′-tetra-tert-butyl-2,2′-[1,2-phenyl­enebis(nitrilo­methyl­idyne)]diphenolato-κ4O,O′,N,N′}zinc(II) ethanol solvate

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

doi:10.1107/S1600536807030863

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(Ethanol-κO){4,4′,6,6′-tetra-tert-butyl-2,2′-[1,2-phenylenebis(nitrilomethylidyne)]diphenolato-κ⁴O,O′,N,N′}zinc(II) ethanol solvate

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

The title compound, [Zn(C₃₆H₄₆N₂O₂)(C₂H₆O)]·C₂H₅OH, adopts a square-pyramidal Zn^II coordination, with the N₂O₂ tetradentate Schiff base ligand bound in the basal plane and the coordinated ethanol molecule occupying the apical site. Inversion-related Zn^II complex molecules are linked via O—H

O hydrogen bonding involving the coordinated and uncoordinated ethanol molecules, forming dimers which are stacked along the c axis. Intramolecular C—H

O and C—H

π interactions are observed in the Zn^II complex.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030863/ci2400sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030863/ci2400Isup2.hkl Contains datablock I

CCDC reference: 654842

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.045
wR factor = 0.133
Data-to-parameter ratio = 19.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.23 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.68 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C37    -   C38     ..       5.04 su
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C39
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1         (2)       2.12
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

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

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

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 Schiff base ligands have played an important role in the development of coordination chemistry as they readily form stable complexes with most transition metal ions (Pal et al., 2005). Zinc complexes with Schiff-bases are importance in biological systems and coordination chemistry (Collinson & Fenton, 1996; Tarafder et al., 2002). Recently, we have reported crystal structures of Zn^II complexes with Schiff base ligands. As a continuation of our research on Schiff base complexes, we report here the crystal structure of the title compound, (I).

The Zn^II complex is characterized by an approximately square-pyramidal Zn^II coordination, with the N₂O₂ tetradentate Schiff-base ligand in the basal plane and an ethanol molecule in the apical site (Fig. 1). The Zn^II atom is displaced 0.025 (5) Å out of the mean N1/N2/O1/O2 basal plane towards the axial atom, O4, of ethanol molecule. The cyclic skeleton of the tetradentate Schiff-base ligand is essentially planar. The dihedral angles between the central benzene ring (C8—C13) and the other two benzene rings (C1—C6 and C15—C20) are 2.96 (11)° and 9.35 (11)°, respectively. Bond lengths and angles observed in the structure are in normal ranges (Allen et al., 1987) and comparable with the related structures (Eltayeb et al., 2007a; 2007b; Eltayeb, Teoh, Fun et al., 2007; Eltayeb, Teoh, Ng et al., 2007; Eltayeb, Teoh, Teh et al., 2007).

Intramolecular C—H···O interactions (Table 1), and C—H···π interactions involving the C8—C13 (centroid Cg1) ring are observed in the complex molecule. Inversion-related Zn^II complex molecules are linked via O—H···O hydrogen bonding (Table 1) involving the coordinated and two free ethanol molecules, forming dimers which are stacked along the c axis (Fig.2). Molecules in the adjacent stacks are linked via C—H···π interactions involving the C15—C20 ring (centroid Cg2).

Related literature top

For bond-length data, see: Allen et al. (1987). For general background on Schiff-base–Zn^II coordination complexes, see: Pal et al. (2005); Collinson & Fenton (1996); Assaf & Chung (1984); Berg & Shi (1996); Tarafder et al. (2002). For related structures, see: Eltayeb, Teoh, Chantrapromma et al. (2007a, 2007b); Eltayeb, Teoh, Fun et al. (2007); Eltayeb, Teoh, Ng et al. (2007); Eltayeb, Teoh, Teh et al. (2007).

Experimental top

The title compound (I) was synthesized by adding 3,5-di-tert-butyl-2-hydroxybenzaldehyde (0.936 g, 4 mmol) to a solution of o-phenylenediamine (0.216 g, 2 mmol) in ethanol 95% (20 ml). 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. A yellow-orange solution was obtained and it was filtered. Orange crystals suitable for X-ray diffraction were formed after 4 d of slow evaporation of the ethanol at room temperature.

Structure description top

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 and PLATON (Spek, 2003).

Figures top

	Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering. C-bound H atoms of the Zn^II complex have been omitted for clarity.
	Fig. 2. The crystal packing of (I), viewed along the b axis. C-bound H atoms of the Zn^II complex have been omitted for clarity. Hydrogen bonds are shown as dashed lines.

(Ethanol-κO){4,4',6,6'-tetra-tert-butyl-2,2'-[1,2- phenylenebis(nitrilomethylidyne)]diphenolato- κ⁴O,O',N,N'}zinc(II) ethanol solvate top

Crystal data top

[Zn(C₃₆H₄₆N₂O₂)(C₂H₆O)]·C₂H₆O	F(000) = 1496
M_r = 696.25	D_x = 1.221 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8959 reflections
a = 13.0909 (3) Å	θ = 1.6–27.5°
b = 24.8935 (6) Å	µ = 0.69 mm⁻¹
c = 11.6289 (3) Å	T = 100 K
β = 92.303 (1)°	Block, orange
V = 3786.55 (16) Å³	0.40 × 0.34 × 0.30 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	8595 independent reflections
Radiation source: fine-focus sealed tube	6701 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
Detector resolution: 8.33 pixels mm^-1	θ_max = 27.5°, θ_min = 1.6°
ω scans	h = −17→15
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −32→32
T_min = 0.770, T_max = 0.822	l = −14→15
32064 measured reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0592P)² + 3.4587P] where P = (F_o² + 2F_c²)/3
8595 reflections	(Δ/σ)_max = 0.003
445 parameters	Δρ_max = 0.72 e Å⁻³
1 restraint	Δρ_min = −0.56 e Å⁻³

Crystal data top

[Zn(C₃₆H₄₆N₂O₂)(C₂H₆O)]·C₂H₆O	V = 3786.55 (16) Å³
M_r = 696.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.0909 (3) Å	µ = 0.69 mm⁻¹
b = 24.8935 (6) Å	T = 100 K
c = 11.6289 (3) Å	0.40 × 0.34 × 0.30 mm
β = 92.303 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	8595 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	6701 reflections with I > 2σ(I)
T_min = 0.770, T_max = 0.822	R_int = 0.049
32064 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	1 restraint
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.72 e Å⁻³
8595 reflections	Δρ_min = −0.56 e Å⁻³
445 parameters

Special details top

Experimental. The low-temparture data was 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	0.97460 (2)	0.576492 (10)	0.80021 (2)	0.01646 (9)
O1	1.08663 (13)	0.62577 (7)	0.78053 (17)	0.0225 (4)
O2	0.87455 (13)	0.63224 (7)	0.83442 (16)	0.0202 (4)
O3	0.92767 (16)	0.55880 (8)	0.62450 (18)	0.0261 (4)
H1O3	0.971 (3)	0.5634 (13)	0.586 (3)	0.031 (10)*
O4	0.9358 (2)	0.44593 (10)	0.5413 (2)	0.0513 (6)
H1O4	0.917 (3)	0.4741 (11)	0.572 (4)	0.077*
N1	1.07893 (15)	0.51318 (8)	0.80696 (18)	0.0165 (4)
N2	0.89009 (15)	0.51947 (8)	0.88074 (18)	0.0173 (4)
C1	1.17831 (18)	0.61734 (9)	0.7472 (2)	0.0178 (5)
C2	1.23835 (18)	0.66228 (9)	0.7098 (2)	0.0169 (5)
C3	1.33454 (18)	0.65251 (9)	0.6715 (2)	0.0190 (5)
H3A	1.3711	0.6816	0.6441	0.023*
C4	1.38200 (18)	0.60149 (10)	0.6706 (2)	0.0187 (5)
C5	1.32620 (18)	0.55910 (10)	0.7100 (2)	0.0194 (5)
H5A	1.3558	0.5251	0.7125	0.023*
C6	1.22513 (18)	0.56528 (9)	0.7471 (2)	0.0173 (5)
C7	1.17450 (18)	0.51729 (9)	0.7821 (2)	0.0181 (5)
H7A	1.2137	0.4862	0.7875	0.022*
C8	1.03533 (18)	0.46422 (9)	0.8427 (2)	0.0171 (5)
C9	1.08428 (19)	0.41423 (9)	0.8405 (2)	0.0196 (5)
H9A	1.1491	0.4114	0.8112	0.024*
C10	1.03601 (19)	0.36891 (9)	0.8821 (2)	0.0203 (5)
H10A	1.0686	0.3358	0.8801	0.024*
C11	0.9397 (2)	0.37277 (10)	0.9264 (2)	0.0225 (5)
H11A	0.9089	0.3424	0.9561	0.027*
C12	0.8891 (2)	0.42147 (10)	0.9268 (2)	0.0218 (5)
H12A	0.8240	0.4235	0.9557	0.026*
C13	0.93529 (18)	0.46790 (9)	0.8839 (2)	0.0172 (5)
C14	0.80138 (18)	0.52882 (9)	0.9231 (2)	0.0179 (5)
H14A	0.7669	0.4992	0.9512	0.022*
C15	0.75093 (18)	0.57960 (9)	0.9315 (2)	0.0170 (5)
C16	0.65790 (18)	0.57868 (9)	0.9900 (2)	0.0186 (5)
H16A	0.6323	0.5458	1.0134	0.022*
C17	0.60436 (18)	0.62436 (10)	1.0133 (2)	0.0185 (5)
C18	0.64779 (18)	0.67355 (10)	0.9770 (2)	0.0180 (5)
H18A	0.6140	0.7052	0.9948	0.022*
C19	0.73647 (18)	0.67789 (9)	0.9171 (2)	0.0172 (5)
C20	0.79118 (18)	0.62952 (9)	0.8911 (2)	0.0169 (5)
C21	1.19322 (18)	0.71917 (9)	0.7153 (2)	0.0191 (5)
C22	1.09384 (19)	0.72357 (10)	0.6404 (2)	0.0245 (6)
H22A	1.0654	0.7589	0.6483	0.037*
H22B	1.0457	0.6973	0.6650	0.037*
H22C	1.1085	0.7173	0.5613	0.037*
C23	1.2677 (2)	0.76128 (10)	0.6729 (3)	0.0261 (6)
H23A	1.3302	0.7597	0.7189	0.039*
H23B	1.2379	0.7963	0.6792	0.039*
H23C	1.2818	0.7542	0.5939	0.039*
C24	1.1715 (2)	0.73315 (10)	0.8407 (2)	0.0260 (6)
H24A	1.2339	0.7312	0.8868	0.039*
H24B	1.1229	0.7081	0.8694	0.039*
H24C	1.1443	0.7689	0.8442	0.039*
C25	1.48993 (19)	0.59658 (10)	0.6245 (2)	0.0225 (5)
C26	1.5621 (2)	0.63712 (12)	0.6854 (3)	0.0311 (6)
H26A	1.5654	0.6299	0.7666	0.047*
H26B	1.5369	0.6729	0.6720	0.047*
H26C	1.6292	0.6339	0.6556	0.047*
C27	1.4859 (2)	0.60832 (13)	0.4953 (3)	0.0354 (7)
H27A	1.4429	0.5824	0.4561	0.053*
H27B	1.5536	0.6063	0.4668	0.053*
H27C	1.4587	0.6437	0.4818	0.053*
C28	1.5348 (2)	0.54038 (11)	0.6454 (3)	0.0345 (7)
H28A	1.4914	0.5141	0.6079	0.052*
H28B	1.5395	0.5332	0.7266	0.052*
H28C	1.6018	0.5386	0.6148	0.052*
C29	0.50307 (19)	0.62484 (10)	1.0739 (2)	0.0213 (5)
C30	0.4188 (2)	0.64933 (12)	0.9945 (2)	0.0290 (6)
H30A	0.4369	0.6855	0.9754	0.043*
H30B	0.3554	0.6494	1.0332	0.043*
H30C	0.4114	0.6284	0.9254	0.043*
C31	0.5145 (2)	0.65778 (12)	1.1846 (2)	0.0304 (6)
H31A	0.5307	0.6943	1.1660	0.046*
H31B	0.5684	0.6429	1.2331	0.046*
H31C	0.4516	0.6568	1.2242	0.046*
C32	0.4692 (2)	0.56795 (12)	1.1064 (4)	0.0420 (8)
H32A	0.4587	0.5468	1.0379	0.063*
H32B	0.4066	0.5699	1.1465	0.063*
H32C	0.5212	0.5515	1.1553	0.063*
C33	0.77535 (18)	0.73289 (9)	0.8761 (2)	0.0184 (5)
C34	0.88318 (19)	0.74462 (10)	0.9275 (2)	0.0218 (5)
H34A	0.9285	0.7160	0.9080	0.033*
H34B	0.8807	0.7473	1.0097	0.033*
H34C	0.9076	0.7778	0.8969	0.033*
C35	0.7060 (2)	0.77923 (10)	0.9124 (2)	0.0231 (5)
H35A	0.6377	0.7732	0.8821	0.035*
H35B	0.7313	0.8125	0.8828	0.035*
H35C	0.7059	0.7810	0.9948	0.035*
C36	0.7769 (2)	0.73394 (10)	0.7447 (2)	0.0228 (5)
H36A	0.8215	0.7062	0.7189	0.034*
H36B	0.8012	0.7683	0.7199	0.034*
H36C	0.7091	0.7280	0.7129	0.034*
C37	0.8406 (3)	0.58757 (15)	0.5761 (3)	0.0432 (8)
H37A	0.8594	0.6249	0.5656	0.052*
H37B	0.7860	0.5865	0.6301	0.052*
C38	0.8021 (3)	0.56542 (16)	0.4642 (3)	0.0540 (10)
H38A	0.7447	0.5863	0.4359	0.081*
H38B	0.7811	0.5288	0.4744	0.081*
H38C	0.8553	0.5668	0.4099	0.081*
C39	0.8839 (4)	0.40238 (17)	0.5901 (4)	0.0609 (11)
H39A	0.9213	0.3911	0.6596	0.073*
H39B	0.8832	0.3725	0.5365	0.073*
C40	0.7779 (4)	0.4149 (3)	0.6186 (6)	0.121 (3)
H40A	0.7463	0.3834	0.6487	0.181*
H40B	0.7404	0.4266	0.5505	0.181*
H40C	0.7780	0.4430	0.6752	0.181*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.01590 (15)	0.01228 (14)	0.02151 (17)	−0.00033 (10)	0.00465 (10)	0.00128 (11)
O1	0.0173 (8)	0.0144 (8)	0.0365 (11)	−0.0007 (6)	0.0084 (7)	0.0024 (7)
O2	0.0183 (8)	0.0145 (8)	0.0283 (10)	0.0009 (6)	0.0084 (7)	0.0015 (7)
O3	0.0229 (10)	0.0326 (11)	0.0231 (11)	0.0059 (8)	0.0041 (8)	0.0004 (8)
O4	0.0597 (16)	0.0464 (15)	0.0491 (16)	−0.0047 (12)	0.0191 (13)	−0.0107 (12)
N1	0.0181 (10)	0.0125 (9)	0.0191 (11)	−0.0015 (7)	0.0027 (8)	0.0003 (8)
N2	0.0185 (10)	0.0120 (9)	0.0214 (11)	0.0007 (7)	0.0028 (8)	0.0002 (8)
C1	0.0168 (11)	0.0162 (11)	0.0206 (12)	−0.0015 (9)	0.0018 (9)	−0.0009 (9)
C2	0.0180 (11)	0.0158 (11)	0.0167 (12)	−0.0019 (9)	−0.0001 (9)	0.0008 (9)
C3	0.0205 (12)	0.0173 (12)	0.0195 (13)	−0.0049 (9)	0.0023 (10)	0.0004 (9)
C4	0.0175 (12)	0.0204 (12)	0.0182 (12)	−0.0001 (9)	0.0017 (9)	−0.0020 (9)
C5	0.0191 (12)	0.0159 (11)	0.0231 (13)	0.0013 (9)	0.0017 (10)	−0.0028 (10)
C6	0.0182 (11)	0.0157 (11)	0.0183 (12)	−0.0019 (9)	0.0031 (9)	0.0008 (9)
C7	0.0191 (12)	0.0139 (11)	0.0215 (13)	0.0014 (9)	0.0014 (9)	−0.0010 (9)
C8	0.0196 (11)	0.0125 (11)	0.0191 (12)	0.0007 (9)	0.0012 (9)	0.0003 (9)
C9	0.0197 (12)	0.0157 (12)	0.0236 (14)	0.0014 (9)	0.0034 (10)	−0.0001 (9)
C10	0.0254 (13)	0.0115 (11)	0.0240 (13)	0.0017 (9)	0.0025 (10)	0.0012 (9)
C11	0.0316 (14)	0.0132 (11)	0.0232 (13)	−0.0036 (10)	0.0058 (11)	0.0023 (10)
C12	0.0228 (12)	0.0183 (12)	0.0248 (14)	−0.0006 (9)	0.0087 (10)	0.0007 (10)
C13	0.0206 (12)	0.0133 (11)	0.0178 (12)	0.0001 (9)	0.0024 (9)	0.0002 (9)
C14	0.0175 (11)	0.0134 (11)	0.0232 (13)	−0.0014 (9)	0.0041 (9)	0.0016 (9)
C15	0.0172 (11)	0.0148 (11)	0.0190 (12)	−0.0010 (9)	0.0021 (9)	−0.0005 (9)
C16	0.0163 (11)	0.0152 (11)	0.0245 (13)	−0.0018 (9)	0.0046 (9)	0.0028 (9)
C17	0.0163 (11)	0.0205 (12)	0.0188 (12)	−0.0006 (9)	0.0021 (9)	0.0017 (9)
C18	0.0187 (11)	0.0174 (11)	0.0180 (12)	0.0037 (9)	0.0021 (9)	−0.0015 (9)
C19	0.0175 (11)	0.0153 (11)	0.0185 (12)	0.0009 (9)	−0.0010 (9)	0.0019 (9)
C20	0.0162 (11)	0.0170 (11)	0.0174 (12)	−0.0005 (9)	0.0016 (9)	0.0001 (9)
C21	0.0198 (12)	0.0140 (11)	0.0233 (13)	−0.0014 (9)	0.0011 (10)	0.0024 (9)
C22	0.0225 (13)	0.0194 (12)	0.0316 (15)	0.0008 (10)	0.0014 (11)	0.0049 (11)
C23	0.0258 (13)	0.0163 (12)	0.0366 (16)	−0.0029 (10)	0.0049 (11)	0.0034 (11)
C24	0.0298 (14)	0.0182 (12)	0.0303 (15)	−0.0010 (10)	0.0067 (11)	−0.0022 (11)
C25	0.0184 (12)	0.0205 (12)	0.0292 (15)	−0.0011 (9)	0.0078 (10)	−0.0016 (10)
C26	0.0190 (13)	0.0313 (15)	0.0433 (18)	−0.0038 (11)	0.0070 (12)	−0.0066 (13)
C27	0.0338 (16)	0.0441 (18)	0.0292 (16)	0.0015 (13)	0.0128 (12)	−0.0008 (13)
C28	0.0241 (14)	0.0263 (14)	0.054 (2)	0.0032 (11)	0.0137 (13)	0.0019 (14)
C29	0.0186 (12)	0.0190 (12)	0.0269 (14)	0.0014 (9)	0.0093 (10)	0.0001 (10)
C30	0.0207 (13)	0.0380 (16)	0.0284 (15)	0.0039 (11)	0.0036 (11)	−0.0069 (12)
C31	0.0264 (14)	0.0390 (16)	0.0261 (15)	0.0023 (11)	0.0065 (11)	−0.0011 (12)
C32	0.0304 (16)	0.0258 (15)	0.072 (2)	0.0002 (12)	0.0278 (16)	0.0049 (15)
C33	0.0220 (12)	0.0132 (11)	0.0200 (13)	−0.0002 (9)	0.0034 (10)	0.0002 (9)
C34	0.0218 (12)	0.0175 (12)	0.0260 (14)	−0.0023 (9)	−0.0003 (10)	0.0006 (10)
C35	0.0278 (13)	0.0151 (12)	0.0268 (14)	0.0026 (10)	0.0044 (11)	0.0023 (10)
C36	0.0300 (14)	0.0169 (12)	0.0217 (13)	−0.0025 (10)	0.0043 (10)	0.0026 (10)
C37	0.0395 (18)	0.051 (2)	0.0380 (19)	0.0229 (15)	−0.0091 (15)	−0.0118 (15)
C38	0.057 (2)	0.058 (2)	0.047 (2)	0.0122 (18)	−0.0054 (18)	−0.0036 (18)
C39	0.082 (3)	0.059 (2)	0.043 (2)	−0.029 (2)	0.011 (2)	−0.0090 (19)
C40	0.060 (3)	0.186 (7)	0.112 (5)	−0.047 (4)	−0.039 (3)	0.067 (5)

Geometric parameters (Å, º) top

Zn1—O1	1.9326 (17)	C23—H23A	0.96
Zn1—O2	1.9600 (17)	C23—H23B	0.96
Zn1—N2	2.049 (2)	C23—H23C	0.96
Zn1—N1	2.0850 (19)	C24—H24A	0.96
Zn1—O3	2.155 (2)	C24—H24B	0.96
O1—C1	1.293 (3)	C24—H24C	0.96
O2—C20	1.299 (3)	C25—C27	1.530 (4)
O3—C37	1.442 (3)	C25—C28	1.533 (4)
O3—H1O3	0.74 (4)	C25—C26	1.536 (4)
O4—C39	1.411 (5)	C26—H26A	0.96
O4—H1O4	0.83 (3)	C26—H26B	0.96
N1—C7	1.299 (3)	C26—H26C	0.96
N1—C8	1.415 (3)	C27—H27A	0.96
N2—C14	1.301 (3)	C27—H27B	0.96
N2—C13	1.413 (3)	C27—H27C	0.96
C1—C6	1.434 (3)	C28—H28A	0.96
C1—C2	1.444 (3)	C28—H28B	0.96
C2—C3	1.374 (3)	C28—H28C	0.96
C2—C21	1.537 (3)	C29—C31	1.529 (4)
C3—C4	1.414 (3)	C29—C32	1.536 (4)
C3—H3A	0.93	C29—C30	1.536 (4)
C4—C5	1.373 (3)	C30—H30A	0.96
C4—C25	1.536 (3)	C30—H30B	0.96
C5—C6	1.416 (3)	C30—H30C	0.96
C5—H5A	0.93	C31—H31A	0.96
C6—C7	1.433 (3)	C31—H31B	0.96
C7—H7A	0.93	C31—H31C	0.96
C8—C9	1.400 (3)	C32—H32A	0.96
C8—C13	1.415 (3)	C32—H32B	0.96
C9—C10	1.389 (3)	C32—H32C	0.96
C9—H9A	0.93	C33—C36	1.529 (4)
C10—C11	1.384 (4)	C33—C35	1.537 (3)
C10—H10A	0.93	C33—C34	1.539 (3)
C11—C12	1.381 (3)	C34—H34A	0.96
C11—H11A	0.93	C34—H34B	0.96
C12—C13	1.405 (3)	C34—H34C	0.96
C12—H12A	0.93	C35—H35A	0.96
C14—C15	1.431 (3)	C35—H35B	0.96
C14—H14A	0.93	C35—H35C	0.96
C15—C16	1.419 (3)	C36—H36A	0.96
C15—C20	1.436 (3)	C36—H36B	0.96
C16—C17	1.369 (3)	C36—H36C	0.96
C16—H16A	0.93	C37—C38	1.483 (5)
C17—C18	1.422 (3)	C37—H37A	0.97
C17—C29	1.526 (3)	C37—H37B	0.97
C18—C19	1.382 (3)	C38—H38A	0.96
C18—H18A	0.93	C38—H38B	0.96
C19—C20	1.439 (3)	C38—H38C	0.96
C19—C33	1.543 (3)	C39—C40	1.473 (7)
C21—C23	1.527 (3)	C39—H39A	0.97
C21—C24	1.536 (4)	C39—H39B	0.97
C21—C22	1.540 (3)	C40—H40A	0.96
C22—H22A	0.96	C40—H40B	0.96
C22—H22B	0.96	C40—H40C	0.96
C22—H22C	0.96

O1—Zn1—O2	95.22 (7)	C21—C24—H24B	109.5
O1—Zn1—N2	156.93 (8)	H24A—C24—H24B	109.5
O2—Zn1—N2	91.17 (8)	C21—C24—H24C	109.5
O1—Zn1—N1	89.15 (7)	H24A—C24—H24C	109.5
O2—Zn1—N1	165.86 (8)	H24B—C24—H24C	109.5
N2—Zn1—N1	79.86 (8)	C27—C25—C28	109.1 (2)
O1—Zn1—O3	101.90 (8)	C27—C25—C26	108.9 (2)
O2—Zn1—O3	99.78 (8)	C28—C25—C26	107.6 (2)
N2—Zn1—O3	98.81 (8)	C27—C25—C4	109.4 (2)
N1—Zn1—O3	92.44 (8)	C28—C25—C4	111.7 (2)
C1—O1—Zn1	130.57 (15)	C26—C25—C4	110.2 (2)
C20—O2—Zn1	130.38 (15)	C25—C26—H26A	109.5
C37—O3—Zn1	117.34 (18)	C25—C26—H26B	109.5
C37—O3—H1O3	107 (3)	H26A—C26—H26B	109.5
Zn1—O3—H1O3	110 (3)	C25—C26—H26C	109.5
C39—O4—H1O4	109 (3)	H26A—C26—H26C	109.5
C7—N1—C8	122.4 (2)	H26B—C26—H26C	109.5
C7—N1—Zn1	124.55 (16)	C25—C27—H27A	109.5
C8—N1—Zn1	113.00 (15)	C25—C27—H27B	109.5
C14—N2—C13	122.1 (2)	H27A—C27—H27B	109.5
C14—N2—Zn1	123.76 (16)	C25—C27—H27C	109.5
C13—N2—Zn1	114.07 (15)	H27A—C27—H27C	109.5
O1—C1—C6	123.3 (2)	H27B—C27—H27C	109.5
O1—C1—C2	119.2 (2)	C25—C28—H28A	109.5
C6—C1—C2	117.5 (2)	C25—C28—H28B	109.5
C3—C2—C1	118.5 (2)	H28A—C28—H28B	109.5
C3—C2—C21	122.4 (2)	C25—C28—H28C	109.5
C1—C2—C21	119.1 (2)	H28A—C28—H28C	109.5
C2—C3—C4	124.7 (2)	H28B—C28—H28C	109.5
C2—C3—H3A	117.6	C17—C29—C31	109.6 (2)
C4—C3—H3A	117.6	C17—C29—C32	111.8 (2)
C5—C4—C3	116.6 (2)	C31—C29—C32	107.9 (3)
C5—C4—C25	124.4 (2)	C17—C29—C30	110.0 (2)
C3—C4—C25	119.0 (2)	C31—C29—C30	109.7 (2)
C4—C5—C6	122.3 (2)	C32—C29—C30	107.9 (2)
C4—C5—H5A	118.8	C29—C30—H30A	109.5
C6—C5—H5A	118.8	C29—C30—H30B	109.5
C5—C6—C7	116.4 (2)	H30A—C30—H30B	109.5
C5—C6—C1	120.2 (2)	C29—C30—H30C	109.5
C7—C6—C1	123.4 (2)	H30A—C30—H30C	109.5
N1—C7—C6	126.1 (2)	H30B—C30—H30C	109.5
N1—C7—H7A	116.9	C29—C31—H31A	109.5
C6—C7—H7A	116.9	C29—C31—H31B	109.5
C9—C8—N1	124.7 (2)	H31A—C31—H31B	109.5
C9—C8—C13	119.6 (2)	C29—C31—H31C	109.5
N1—C8—C13	115.7 (2)	H31A—C31—H31C	109.5
C10—C9—C8	120.0 (2)	H31B—C31—H31C	109.5
C10—C9—H9A	120.0	C29—C32—H32A	109.5
C8—C9—H9A	120.0	C29—C32—H32B	109.5
C11—C10—C9	120.5 (2)	H32A—C32—H32B	109.5
C11—C10—H10A	119.8	C29—C32—H32C	109.5
C9—C10—H10A	119.8	H32A—C32—H32C	109.5
C12—C11—C10	120.4 (2)	H32B—C32—H32C	109.5
C12—C11—H11A	119.8	C36—C33—C35	107.0 (2)
C10—C11—H11A	119.8	C36—C33—C34	109.6 (2)
C11—C12—C13	120.5 (2)	C35—C33—C34	107.1 (2)
C11—C12—H12A	119.7	C36—C33—C19	110.0 (2)
C13—C12—H12A	119.7	C35—C33—C19	112.1 (2)
C12—C13—N2	124.8 (2)	C34—C33—C19	110.93 (19)
C12—C13—C8	118.9 (2)	C33—C34—H34A	109.5
N2—C13—C8	116.2 (2)	C33—C34—H34B	109.5
N2—C14—C15	127.2 (2)	H34A—C34—H34B	109.5
N2—C14—H14A	116.4	C33—C34—H34C	109.5
C15—C14—H14A	116.4	H34A—C34—H34C	109.5
C16—C15—C14	115.2 (2)	H34B—C34—H34C	109.5
C16—C15—C20	120.3 (2)	C33—C35—H35A	109.5
C14—C15—C20	124.5 (2)	C33—C35—H35B	109.5
C17—C16—C15	122.5 (2)	H35A—C35—H35B	109.5
C17—C16—H16A	118.7	C33—C35—H35C	109.5
C15—C16—H16A	118.7	H35A—C35—H35C	109.5
C16—C17—C18	116.3 (2)	H35B—C35—H35C	109.5
C16—C17—C29	124.0 (2)	C33—C36—H36A	109.5
C18—C17—C29	119.7 (2)	C33—C36—H36B	109.5
C19—C18—C17	124.8 (2)	H36A—C36—H36B	109.5
C19—C18—H18A	117.6	C33—C36—H36C	109.5
C17—C18—H18A	117.6	H36A—C36—H36C	109.5
C18—C19—C20	118.4 (2)	H36B—C36—H36C	109.5
C18—C19—C33	121.3 (2)	O3—C37—C38	113.2 (3)
C20—C19—C33	120.3 (2)	O3—C37—H37A	108.9
O2—C20—C15	122.5 (2)	C38—C37—H37A	108.9
O2—C20—C19	119.9 (2)	O3—C37—H37B	108.9
C15—C20—C19	117.6 (2)	C38—C37—H37B	108.9
C23—C21—C24	107.2 (2)	H37A—C37—H37B	107.8
C23—C21—C2	111.6 (2)	C37—C38—H38A	109.5
C24—C21—C2	109.5 (2)	C37—C38—H38B	109.5
C23—C21—C22	107.7 (2)	H38A—C38—H38B	109.5
C24—C21—C22	109.7 (2)	C37—C38—H38C	109.5
C2—C21—C22	111.1 (2)	H38A—C38—H38C	109.5
C21—C22—H22A	109.5	H38B—C38—H38C	109.5
C21—C22—H22B	109.5	O4—C39—C40	113.6 (4)
H22A—C22—H22B	109.5	O4—C39—H39A	108.8
C21—C22—H22C	109.5	C40—C39—H39A	108.8
H22A—C22—H22C	109.5	O4—C39—H39B	108.8
H22B—C22—H22C	109.5	C40—C39—H39B	108.8
C21—C23—H23A	109.5	H39A—C39—H39B	107.7
C21—C23—H23B	109.5	C39—C40—H40A	109.5
H23A—C23—H23B	109.5	C39—C40—H40B	109.5
C21—C23—H23C	109.5	H40A—C40—H40B	109.5
H23A—C23—H23C	109.5	C39—C40—H40C	109.5
H23B—C23—H23C	109.5	H40A—C40—H40C	109.5
C21—C24—H24A	109.5	H40B—C40—H40C	109.5

O2—Zn1—O1—C1	−174.0 (2)	C10—C11—C12—C13	−1.0 (4)
N2—Zn1—O1—C1	80.5 (3)	C11—C12—C13—N2	−179.9 (2)
N1—Zn1—O1—C1	19.4 (2)	C11—C12—C13—C8	−1.4 (4)
O3—Zn1—O1—C1	−72.9 (2)	C14—N2—C13—C12	3.1 (4)
O1—Zn1—O2—C20	−155.7 (2)	Zn1—N2—C13—C12	−175.2 (2)
N2—Zn1—O2—C20	2.2 (2)	C14—N2—C13—C8	−175.3 (2)
N1—Zn1—O2—C20	−48.1 (4)	Zn1—N2—C13—C8	6.3 (3)
O3—Zn1—O2—C20	101.3 (2)	C9—C8—C13—C12	3.0 (4)
O1—Zn1—O3—C37	−99.0 (2)	N1—C8—C13—C12	−176.5 (2)
O2—Zn1—O3—C37	−1.5 (2)	C9—C8—C13—N2	−178.5 (2)
N2—Zn1—O3—C37	91.3 (2)	N1—C8—C13—N2	2.0 (3)
N1—Zn1—O3—C37	171.4 (2)	C13—N2—C14—C15	175.8 (2)
O1—Zn1—N1—C7	−10.4 (2)	Zn1—N2—C14—C15	−6.0 (4)
O2—Zn1—N1—C7	−118.7 (3)	N2—C14—C15—C16	−175.2 (2)
N2—Zn1—N1—C7	−170.0 (2)	N2—C14—C15—C20	1.2 (4)
O3—Zn1—N1—C7	91.5 (2)	C14—C15—C16—C17	174.7 (2)
O1—Zn1—N1—C8	169.21 (16)	C20—C15—C16—C17	−1.8 (4)
O2—Zn1—N1—C8	60.9 (4)	C15—C16—C17—C18	−0.8 (4)
N2—Zn1—N1—C8	9.60 (16)	C15—C16—C17—C29	178.7 (2)
O3—Zn1—N1—C8	−88.92 (17)	C16—C17—C18—C19	2.6 (4)
O1—Zn1—N2—C14	110.3 (2)	C29—C17—C18—C19	−177.0 (2)
O2—Zn1—N2—C14	4.1 (2)	C17—C18—C19—C20	−1.5 (4)
N1—Zn1—N2—C14	173.1 (2)	C17—C18—C19—C33	177.1 (2)
O3—Zn1—N2—C14	−96.0 (2)	Zn1—O2—C20—C15	−6.8 (3)
O1—Zn1—N2—C13	−71.3 (3)	Zn1—O2—C20—C19	172.24 (16)
O2—Zn1—N2—C13	−177.59 (16)	C16—C15—C20—O2	−178.1 (2)
N1—Zn1—N2—C13	−8.59 (16)	C14—C15—C20—O2	5.7 (4)
O3—Zn1—N2—C13	82.33 (17)	C16—C15—C20—C19	2.9 (3)
Zn1—O1—C1—C6	−17.9 (4)	C14—C15—C20—C19	−173.4 (2)
Zn1—O1—C1—C2	163.24 (17)	C18—C19—C20—O2	179.7 (2)
O1—C1—C2—C3	−178.1 (2)	C33—C19—C20—O2	1.1 (3)
C6—C1—C2—C3	2.9 (3)	C18—C19—C20—C15	−1.3 (3)
O1—C1—C2—C21	2.5 (3)	C33—C19—C20—C15	−179.9 (2)
C6—C1—C2—C21	−176.5 (2)	C3—C2—C21—C23	0.4 (3)
C1—C2—C3—C4	−3.1 (4)	C1—C2—C21—C23	179.8 (2)
C21—C2—C3—C4	176.3 (2)	C3—C2—C21—C24	−118.1 (3)
C2—C3—C4—C5	0.8 (4)	C1—C2—C21—C24	61.2 (3)
C2—C3—C4—C25	179.7 (2)	C3—C2—C21—C22	120.6 (3)
C3—C4—C5—C6	1.6 (4)	C1—C2—C21—C22	−60.0 (3)
C25—C4—C5—C6	−177.2 (2)	C5—C4—C25—C27	111.9 (3)
C4—C5—C6—C7	177.7 (2)	C3—C4—C25—C27	−67.0 (3)
C4—C5—C6—C1	−1.6 (4)	C5—C4—C25—C28	−9.1 (4)
O1—C1—C6—C5	−179.6 (2)	C3—C4—C25—C28	172.1 (2)
C2—C1—C6—C5	−0.7 (3)	C5—C4—C25—C26	−128.5 (3)
O1—C1—C6—C7	1.1 (4)	C3—C4—C25—C26	52.7 (3)
C2—C1—C6—C7	180.0 (2)	C16—C17—C29—C31	120.1 (3)
C8—N1—C7—C6	−179.0 (2)	C18—C17—C29—C31	−60.4 (3)
Zn1—N1—C7—C6	0.6 (4)	C16—C17—C29—C32	0.6 (4)
C5—C6—C7—N1	−172.1 (2)	C18—C17—C29—C32	−179.9 (3)
C1—C6—C7—N1	7.2 (4)	C16—C17—C29—C30	−119.2 (3)
C7—N1—C8—C9	−9.0 (4)	C18—C17—C29—C30	60.3 (3)
Zn1—N1—C8—C9	171.4 (2)	C18—C19—C33—C36	−117.6 (3)
C7—N1—C8—C13	170.4 (2)	C20—C19—C33—C36	60.9 (3)
Zn1—N1—C8—C13	−9.2 (3)	C18—C19—C33—C35	1.3 (3)
N1—C8—C9—C10	177.3 (2)	C20—C19—C33—C35	179.8 (2)
C13—C8—C9—C10	−2.1 (4)	C18—C19—C33—C34	120.9 (2)
C8—C9—C10—C11	−0.3 (4)	C20—C19—C33—C34	−60.6 (3)
C9—C10—C11—C12	1.9 (4)	Zn1—O3—C37—C38	−168.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O4ⁱ	0.75 (4)	1.97 (4)	2.684 (3)	160 (4)
O4—H1O4···O3	0.83 (3)	2.20 (3)	2.975 (3)	156 (4)
C22—H22B···O1	0.96	2.28	2.933 (3)	124
C24—H24B···O1	0.96	2.34	2.968 (3)	123
C34—H34A···O2	0.96	2.35	3.000 (3)	124
C36—H36A···O2	0.96	2.37	3.004 (3)	124
C39—H39A···Cg1	0.97	2.79	3.641 (5)	146
C26—H26A···Cg2ⁱⁱ	0.96	2.73	3.534 (3)	142

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

Experimental details

Crystal data
Chemical formula	[Zn(C₃₆H₄₆N₂O₂)(C₂H₆O)]·C₂H₆O
M_r	696.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.0909 (3), 24.8935 (6), 11.6289 (3)
β (°)	92.303 (1)
V (Å³)	3786.55 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.69
Crystal size (mm)	0.40 × 0.34 × 0.30

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.770, 0.822
No. of measured, independent and observed [I > 2σ(I)] reflections	32064, 8595, 6701
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.133, 1.08
No. of reflections	8595
No. of parameters	445
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.56

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O4ⁱ	0.75 (4)	1.97 (4)	2.684 (3)	160 (4)
O4—H1O4···O3	0.83 (3)	2.20 (3)	2.975 (3)	156 (4)
C22—H22B···O1	0.96	2.28	2.933 (3)	124
C24—H24B···O1	0.96	2.34	2.968 (3)	123
C34—H34A···O2	0.96	2.35	3.000 (3)	124
C36—H36A···O2	0.96	2.37	3.004 (3)	124
C39—H39A···Cg1	0.97	2.79	3.641 (5)	146
C26—H26A···Cg2ⁱⁱ	0.96	2.73	3.534 (3)	142

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

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