Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030863/ci2400sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030863/ci2400Isup2.hkl |
CCDC reference: 654842
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
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.
Hydroxyl H atoms were located in a difference map and refined with a O4-H1O4 distance restraint of 0.82 Å. The remainning H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances in the range 0.93–0.96 Å. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. The highest residual peak is located 0.91 Å from H39B and the deepest hole is located 0.45 Å from C38.
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 ZnII 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 ZnII complex is characterized by an approximately square-pyramidal ZnII coordination, with the N2O2 tetradentate Schiff-base ligand in the basal plane and an ethanol molecule in the apical site (Fig. 1). The ZnII 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 ZnII 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).
For bond-length data, see: Allen et al. (1987). For general background on Schiff-base–ZnII 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).
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).
[Zn(C36H46N2O2)(C2H6O)]·C2H6O | F(000) = 1496 |
Mr = 696.25 | Dx = 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 |
Bruker SMART APEXII CCD area-detector diffractometer | 8595 independent reflections |
Radiation source: fine-focus sealed tube | 6701 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
Detector resolution: 8.33 pixels mm-1 | θmax = 27.5°, θmin = 1.6° |
ω scans | h = −17→15 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −32→32 |
Tmin = 0.770, Tmax = 0.822 | l = −14→15 |
32064 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)] = 0.045 | 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(Fo2) + (0.0592P)2 + 3.4587P] where P = (Fo2 + 2Fc2)/3 |
8595 reflections | (Δ/σ)max = 0.003 |
445 parameters | Δρmax = 0.72 e Å−3 |
1 restraint | Δρmin = −0.56 e Å−3 |
[Zn(C36H46N2O2)(C2H6O)]·C2H6O | V = 3786.55 (16) Å3 |
Mr = 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)° |
Bruker SMART APEXII CCD area-detector diffractometer | 8595 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 6701 reflections with I > 2σ(I) |
Tmin = 0.770, Tmax = 0.822 | Rint = 0.049 |
32064 measured reflections |
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 | Δρmax = 0.72 e Å−3 |
8595 reflections | Δρmin = −0.56 e Å−3 |
445 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.770, 0.822 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 32064, 8595, 6701 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.72, −0.56 |
Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL and PLATON (Spek, 2003).
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. |
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 ZnII 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 ZnII complex is characterized by an approximately square-pyramidal ZnII coordination, with the N2O2 tetradentate Schiff-base ligand in the basal plane and an ethanol molecule in the apical site (Fig. 1). The ZnII 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 ZnII 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).