metal-organic compounds
A triclinic polymorph of dichlorido(2-{[2-(isopropylammonio)ethyl]iminomethyl-κN}-5-methoxyphenolato-κO1)zinc
aZibo Vocational Institute, Zibo 255314, People's Republic of China
*Correspondence e-mail: aitianpei@126.com
The title compound, [ZnCl2(C13H20N2O2)], was first reported in the monoclinic P21/n [Han et al. (2010). Acta Cryst. E66, m469]. This investigation reveals a triclinic polymorph in the P-1 with an that contains two independent molecules of the mononuclear zinc(II) complex. In each molecule, the ZnII atoms are coordinated in a bidentate fashion by the phenolate O and imine N atoms of the Schiff base ligand. Two Cl− anions complete the tetrahedral coordination in each case. The most obvious difference between the two forms is that the Zn—L (L = O, N, Cl) bond lengths in both unique molecules are longer than those found in the monoclinic polymorph, or indeed in other similar complexes. In the crystal, molecules are linked through N—H⋯O and N—H⋯Cl hydrogen bonds, forming chains along the b axis.
Related literature
For the structures of zinc complexes with Schiff base ligands, see: Munro et al. (2009); Granifo et al. (2006). For a monoclinic polymorph of the title compound in the P21/n, see: Han et al. (2010). For bond lengths in related zinc complexes, see: Ali et al. (2008); Zhu (2008); Wang (2007).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.
Supporting information
10.1107/S1600536812014341/sj5230sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812014341/sj5230Isup2.hkl
4-Methoxysalicylaldehyde (0.1 mmol, 15.2 mg), N-isopropylethane-1,2-diamine (0.1 mmol, 10.2 mg), and zinc chloride (0.1 mmol, 13.7 mg) were dissolved in methanol (15 ml). The mixture was stirred at reflux for 30 min and cooled to room temperature. Small and colorless block-like single crystals were obtained by slow evaporation of the solution in air.
Hydrogen atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97 Å, N—H = 0.90 Å, and with Uiso(H) = 1.2Ueq(C,N) and 1.5Ueq(Cmethyl).
Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.[ZnCl2(C13H20N2O2)] | Z = 4 |
Mr = 372.58 | F(000) = 768 |
Triclinic, P1 | Dx = 1.362 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.491 (3) Å | Cell parameters from 3080 reflections |
b = 12.351 (2) Å | θ = 2.5–24.5° |
c = 22.803 (3) Å | µ = 1.65 mm−1 |
α = 90.707 (2)° | T = 298 K |
β = 96.201 (2)° | Block, colorless |
γ = 90.660 (2)° | 0.13 × 0.10 × 0.08 mm |
V = 1817.1 (9) Å3 |
Bruker SMART CCD area-detector diffractometer | 5775 independent reflections |
Radiation source: fine-focus sealed tube | 4093 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω scans | θmax = 25.0°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −7→7 |
Tmin = 0.814, Tmax = 0.880 | k = −14→14 |
8230 measured reflections | l = −27→24 |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.181 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0975P)2 + 0.557P] where P = (Fo2 + 2Fc2)/3 |
5775 reflections | (Δ/σ)max < 0.001 |
367 parameters | Δρmax = 0.63 e Å−3 |
0 restraints | Δρmin = −0.57 e Å−3 |
[ZnCl2(C13H20N2O2)] | γ = 90.660 (2)° |
Mr = 372.58 | V = 1817.1 (9) Å3 |
Triclinic, P1 | Z = 4 |
a = 6.491 (3) Å | Mo Kα radiation |
b = 12.351 (2) Å | µ = 1.65 mm−1 |
c = 22.803 (3) Å | T = 298 K |
α = 90.707 (2)° | 0.13 × 0.10 × 0.08 mm |
β = 96.201 (2)° |
Bruker SMART CCD area-detector diffractometer | 5775 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 4093 reflections with I > 2σ(I) |
Tmin = 0.814, Tmax = 0.880 | Rint = 0.027 |
8230 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.181 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.63 e Å−3 |
5775 reflections | Δρmin = −0.57 e Å−3 |
367 parameters |
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 | 0.74321 (12) | 0.83418 (5) | 0.23642 (3) | 0.0441 (2) | |
Cl1 | 0.9409 (3) | 0.81988 (11) | 0.32920 (7) | 0.0474 (4) | |
Cl2 | 0.4987 (2) | 0.97077 (12) | 0.22753 (8) | 0.0521 (4) | |
O1 | 0.9277 (7) | 0.8554 (3) | 0.17284 (19) | 0.0498 (11) | |
O2 | 1.4088 (9) | 0.7419 (4) | 0.0412 (2) | 0.0766 (16) | |
N1 | 0.6280 (7) | 0.6838 (4) | 0.2085 (2) | 0.0397 (12) | |
N2 | 0.5954 (8) | 0.5896 (3) | 0.3369 (2) | 0.0392 (11) | |
H2A | 0.5568 | 0.5194 | 0.3339 | 0.047* | |
H2B | 0.7167 | 0.5959 | 0.3214 | 0.047* | |
C1 | 0.8974 (9) | 0.6630 (4) | 0.1382 (3) | 0.0423 (14) | |
C2 | 0.9929 (9) | 0.7736 (4) | 0.1399 (2) | 0.0396 (14) | |
C3 | 1.1644 (10) | 0.7914 (5) | 0.1059 (3) | 0.0481 (16) | |
H3 | 1.2275 | 0.8595 | 0.1070 | 0.058* | |
C4 | 1.2390 (11) | 0.7097 (5) | 0.0713 (3) | 0.0508 (16) | |
C5 | 1.1530 (13) | 0.6025 (6) | 0.0688 (3) | 0.065 (2) | |
H5 | 1.2054 | 0.5479 | 0.0465 | 0.078* | |
C6 | 0.9840 (12) | 0.5833 (5) | 0.1021 (3) | 0.063 (2) | |
H6 | 0.9252 | 0.5142 | 0.1003 | 0.076* | |
C7 | 0.7202 (10) | 0.6298 (5) | 0.1696 (3) | 0.0448 (15) | |
H7 | 0.6669 | 0.5608 | 0.1604 | 0.054* | |
C8 | 0.4381 (10) | 0.6345 (5) | 0.2314 (3) | 0.0523 (17) | |
H8A | 0.4358 | 0.5571 | 0.2238 | 0.063* | |
H8B | 0.3149 | 0.6645 | 0.2101 | 0.063* | |
C9 | 0.4320 (10) | 0.6553 (5) | 0.2982 (3) | 0.0443 (15) | |
H9A | 0.2951 | 0.6364 | 0.3086 | 0.053* | |
H9B | 0.4555 | 0.7318 | 0.3067 | 0.053* | |
C10 | 0.6342 (12) | 0.6199 (6) | 0.4030 (3) | 0.0606 (19) | |
H10 | 0.6890 | 0.6942 | 0.4057 | 0.073* | |
C11 | 0.8045 (14) | 0.5466 (7) | 0.4341 (4) | 0.088 (3) | |
H11A | 0.7653 | 0.4720 | 0.4274 | 0.131* | |
H11B | 0.8198 | 0.5621 | 0.4758 | 0.131* | |
H11C | 0.9336 | 0.5606 | 0.4185 | 0.131* | |
C12 | 0.4325 (15) | 0.6195 (8) | 0.4329 (4) | 0.095 (3) | |
H12A | 0.3364 | 0.6690 | 0.4131 | 0.142* | |
H12B | 0.4624 | 0.6413 | 0.4735 | 0.142* | |
H12C | 0.3728 | 0.5478 | 0.4306 | 0.142* | |
C13 | 1.4981 (15) | 0.6614 (8) | 0.0035 (4) | 0.097 (3) | |
H13A | 1.5361 | 0.5983 | 0.0262 | 0.146* | |
H13B | 1.6189 | 0.6918 | −0.0112 | 0.146* | |
H13C | 1.3977 | 0.6416 | −0.0290 | 0.146* | |
Zn2 | 0.75666 (12) | 0.33416 (5) | 0.26356 (3) | 0.0443 (2) | |
Cl3 | 1.0020 (2) | 0.47085 (11) | 0.27261 (8) | 0.0523 (4) | |
Cl4 | 0.5584 (2) | 0.31981 (11) | 0.17081 (7) | 0.0475 (4) | |
O3 | 0.5732 (7) | 0.3560 (3) | 0.32735 (19) | 0.0482 (11) | |
O4 | 0.0905 (9) | 0.2412 (4) | 0.4588 (2) | 0.0797 (17) | |
N3 | 0.8731 (7) | 0.1838 (3) | 0.2917 (2) | 0.0390 (12) | |
N4 | 0.9042 (8) | 0.0893 (4) | 0.1632 (2) | 0.0422 (12) | |
H4A | 0.7834 | 0.0954 | 0.1789 | 0.051* | |
H4B | 0.9398 | 0.0191 | 0.1652 | 0.051* | |
C14 | 0.6016 (10) | 0.1639 (5) | 0.3615 (3) | 0.0453 (15) | |
C15 | 0.5066 (9) | 0.2740 (4) | 0.3594 (3) | 0.0415 (15) | |
C16 | 0.3387 (10) | 0.2910 (5) | 0.3940 (3) | 0.0495 (16) | |
H16 | 0.2789 | 0.3591 | 0.3939 | 0.059* | |
C17 | 0.2592 (11) | 0.2094 (5) | 0.4285 (3) | 0.0544 (18) | |
C18 | 0.3474 (12) | 0.1040 (6) | 0.4310 (3) | 0.061 (2) | |
H18 | 0.2961 | 0.0503 | 0.4539 | 0.074* | |
C19 | 0.5152 (12) | 0.0830 (5) | 0.3975 (3) | 0.063 (2) | |
H19 | 0.5722 | 0.0142 | 0.3989 | 0.075* | |
C20 | 0.7798 (10) | 0.1295 (5) | 0.3312 (3) | 0.0454 (16) | |
H20 | 0.8328 | 0.0616 | 0.3409 | 0.054* | |
C21 | 1.0593 (10) | 0.1347 (5) | 0.2682 (3) | 0.0521 (17) | |
H21A | 1.0568 | 0.0572 | 0.2745 | 0.063* | |
H21B | 1.1838 | 0.1641 | 0.2904 | 0.063* | |
C22 | 1.0700 (10) | 0.1552 (5) | 0.2021 (3) | 0.0443 (15) | |
H22A | 1.0505 | 0.2317 | 0.1945 | 0.053* | |
H22B | 1.2062 | 0.1360 | 0.1919 | 0.053* | |
C23 | 0.8673 (12) | 0.1201 (5) | 0.0974 (3) | 0.0581 (18) | |
H23 | 0.8154 | 0.1943 | 0.0958 | 0.070* | |
C24 | 0.6975 (15) | 0.0471 (7) | 0.0662 (4) | 0.088 (3) | |
H24A | 0.7425 | −0.0267 | 0.0676 | 0.132* | |
H24B | 0.6691 | 0.0685 | 0.0259 | 0.132* | |
H24C | 0.5740 | 0.0535 | 0.0856 | 0.132* | |
C25 | 1.0646 (15) | 0.1192 (8) | 0.0672 (4) | 0.092 (3) | |
H25A | 1.1609 | 0.1720 | 0.0858 | 0.138* | |
H25B | 1.0327 | 0.1364 | 0.0263 | 0.138* | |
H25C | 1.1251 | 0.0487 | 0.0705 | 0.138* | |
C26 | 0.0028 (15) | 0.1620 (7) | 0.4963 (4) | 0.093 (3) | |
H26A | −0.0352 | 0.0973 | 0.4738 | 0.140* | |
H26B | −0.1179 | 0.1915 | 0.5112 | 0.140* | |
H26C | 0.1036 | 0.1450 | 0.5288 | 0.140* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0476 (5) | 0.0345 (4) | 0.0517 (5) | −0.0044 (3) | 0.0124 (4) | −0.0003 (3) |
Cl1 | 0.0494 (10) | 0.0459 (8) | 0.0460 (9) | −0.0042 (7) | 0.0015 (7) | 0.0037 (6) |
Cl2 | 0.0399 (10) | 0.0434 (8) | 0.0735 (11) | 0.0052 (7) | 0.0088 (8) | −0.0091 (7) |
O1 | 0.055 (3) | 0.036 (2) | 0.062 (3) | −0.0052 (19) | 0.025 (2) | −0.0056 (19) |
O2 | 0.091 (4) | 0.074 (3) | 0.073 (4) | 0.014 (3) | 0.045 (3) | 0.006 (3) |
N1 | 0.035 (3) | 0.040 (3) | 0.044 (3) | −0.003 (2) | 0.001 (2) | 0.006 (2) |
N2 | 0.041 (3) | 0.037 (2) | 0.040 (3) | −0.001 (2) | 0.005 (2) | 0.001 (2) |
C1 | 0.038 (4) | 0.042 (3) | 0.046 (3) | 0.000 (3) | 0.000 (3) | 0.000 (3) |
C2 | 0.046 (4) | 0.035 (3) | 0.037 (3) | 0.006 (3) | 0.000 (3) | 0.006 (2) |
C3 | 0.048 (4) | 0.046 (3) | 0.052 (4) | 0.002 (3) | 0.011 (3) | 0.008 (3) |
C4 | 0.057 (5) | 0.060 (4) | 0.039 (4) | 0.019 (3) | 0.015 (3) | 0.009 (3) |
C5 | 0.079 (6) | 0.055 (4) | 0.066 (5) | 0.008 (4) | 0.028 (4) | −0.010 (3) |
C6 | 0.075 (5) | 0.044 (4) | 0.071 (5) | −0.005 (3) | 0.012 (4) | −0.013 (3) |
C7 | 0.048 (4) | 0.036 (3) | 0.050 (4) | −0.007 (3) | 0.004 (3) | −0.005 (3) |
C8 | 0.050 (4) | 0.057 (4) | 0.049 (4) | −0.016 (3) | 0.003 (3) | 0.004 (3) |
C9 | 0.035 (4) | 0.042 (3) | 0.057 (4) | 0.001 (3) | 0.010 (3) | 0.007 (3) |
C10 | 0.070 (5) | 0.059 (4) | 0.053 (4) | −0.011 (4) | 0.011 (4) | −0.009 (3) |
C11 | 0.092 (7) | 0.110 (7) | 0.058 (5) | 0.004 (5) | −0.005 (5) | 0.001 (5) |
C12 | 0.092 (7) | 0.123 (8) | 0.073 (6) | −0.013 (6) | 0.033 (5) | −0.025 (5) |
C13 | 0.105 (8) | 0.115 (7) | 0.082 (7) | 0.027 (6) | 0.052 (6) | 0.003 (5) |
Zn2 | 0.0480 (5) | 0.0349 (4) | 0.0518 (5) | −0.0010 (3) | 0.0141 (4) | −0.0034 (3) |
Cl3 | 0.0424 (10) | 0.0413 (8) | 0.0741 (11) | −0.0101 (7) | 0.0106 (8) | 0.0054 (7) |
Cl4 | 0.0507 (10) | 0.0458 (8) | 0.0448 (9) | 0.0017 (7) | 0.0011 (7) | −0.0079 (6) |
O3 | 0.054 (3) | 0.034 (2) | 0.060 (3) | −0.0038 (19) | 0.024 (2) | −0.0033 (19) |
O4 | 0.092 (4) | 0.076 (3) | 0.079 (4) | −0.016 (3) | 0.049 (3) | −0.009 (3) |
N3 | 0.034 (3) | 0.036 (2) | 0.045 (3) | 0.005 (2) | 0.000 (2) | −0.006 (2) |
N4 | 0.051 (3) | 0.037 (2) | 0.040 (3) | −0.004 (2) | 0.010 (2) | −0.004 (2) |
C14 | 0.043 (4) | 0.047 (3) | 0.046 (4) | −0.004 (3) | 0.007 (3) | −0.004 (3) |
C15 | 0.036 (4) | 0.045 (3) | 0.043 (3) | −0.007 (3) | 0.003 (3) | −0.014 (3) |
C16 | 0.050 (4) | 0.046 (3) | 0.053 (4) | −0.001 (3) | 0.007 (3) | −0.010 (3) |
C17 | 0.065 (5) | 0.052 (4) | 0.048 (4) | −0.017 (3) | 0.012 (3) | −0.007 (3) |
C18 | 0.070 (5) | 0.063 (4) | 0.055 (4) | −0.016 (4) | 0.023 (4) | 0.006 (3) |
C19 | 0.073 (5) | 0.046 (4) | 0.070 (5) | −0.004 (3) | 0.008 (4) | 0.010 (3) |
C20 | 0.051 (4) | 0.038 (3) | 0.046 (4) | 0.001 (3) | 0.000 (3) | −0.004 (3) |
C21 | 0.043 (4) | 0.058 (4) | 0.053 (4) | −0.002 (3) | 0.001 (3) | −0.019 (3) |
C22 | 0.037 (4) | 0.040 (3) | 0.058 (4) | 0.000 (3) | 0.013 (3) | −0.004 (3) |
C23 | 0.073 (5) | 0.047 (4) | 0.054 (4) | 0.003 (3) | 0.003 (4) | 0.005 (3) |
C24 | 0.103 (7) | 0.101 (6) | 0.057 (5) | −0.015 (5) | −0.006 (5) | −0.009 (4) |
C25 | 0.096 (7) | 0.123 (8) | 0.061 (5) | 0.000 (6) | 0.025 (5) | 0.012 (5) |
C26 | 0.096 (8) | 0.101 (7) | 0.088 (7) | −0.029 (6) | 0.044 (6) | 0.000 (5) |
Zn1—O1 | 1.995 (4) | Zn2—O3 | 1.994 (4) |
Zn1—N1 | 2.061 (4) | Zn2—N3 | 2.095 (5) |
Zn1—Cl2 | 2.3252 (18) | Zn2—Cl3 | 2.2994 (16) |
Zn1—Cl1 | 2.3628 (17) | Zn2—Cl4 | 2.3575 (16) |
O1—C2 | 1.351 (6) | O3—C15 | 1.350 (7) |
O2—C4 | 1.416 (8) | O4—C17 | 1.414 (8) |
O2—C13 | 1.471 (9) | O4—C26 | 1.458 (8) |
N1—C7 | 1.304 (7) | N3—C20 | 1.323 (7) |
N1—C8 | 1.514 (7) | N3—C21 | 1.505 (8) |
N2—C10 | 1.543 (8) | N4—C22 | 1.537 (7) |
N2—C9 | 1.547 (7) | N4—C23 | 1.548 (8) |
N2—H2A | 0.9000 | N4—H4A | 0.9000 |
N2—H2B | 0.8999 | N4—H4B | 0.9000 |
C1—C6 | 1.433 (9) | C14—C19 | 1.448 (9) |
C1—C7 | 1.475 (8) | C14—C20 | 1.474 (9) |
C1—C2 | 1.492 (7) | C14—C15 | 1.498 (8) |
C2—C3 | 1.440 (8) | C15—C16 | 1.430 (8) |
C3—C4 | 1.395 (8) | C16—C17 | 1.412 (9) |
C3—H3 | 0.9300 | C16—H16 | 0.9300 |
C4—C5 | 1.429 (9) | C17—C18 | 1.428 (10) |
C5—C6 | 1.419 (10) | C18—C19 | 1.420 (10) |
C5—H5 | 0.9300 | C18—H18 | 0.9300 |
C6—H6 | 0.9300 | C19—H19 | 0.9300 |
C7—H7 | 0.9300 | C20—H20 | 0.9300 |
C8—C9 | 1.546 (9) | C21—C22 | 1.540 (9) |
C8—H8A | 0.9700 | C21—H21A | 0.9700 |
C8—H8B | 0.9700 | C21—H21B | 0.9700 |
C9—H9A | 0.9700 | C22—H22A | 0.9700 |
C9—H9B | 0.9700 | C22—H22B | 0.9700 |
C10—C12 | 1.539 (11) | C23—C25 | 1.518 (11) |
C10—C11 | 1.553 (11) | C23—C24 | 1.524 (10) |
C10—H10 | 0.9800 | C23—H23 | 0.9800 |
C11—H11A | 0.9600 | C24—H24A | 0.9600 |
C11—H11B | 0.9600 | C24—H24B | 0.9600 |
C11—H11C | 0.9600 | C24—H24C | 0.9600 |
C12—H12A | 0.9600 | C25—H25A | 0.9600 |
C12—H12B | 0.9600 | C25—H25B | 0.9600 |
C12—H12C | 0.9600 | C25—H25C | 0.9600 |
C13—H13A | 0.9600 | C26—H26A | 0.9600 |
C13—H13B | 0.9600 | C26—H26B | 0.9600 |
C13—H13C | 0.9600 | C26—H26C | 0.9600 |
O1—Zn1—N1 | 96.96 (18) | O3—Zn2—N3 | 96.87 (18) |
O1—Zn1—Cl2 | 107.23 (13) | O3—Zn2—Cl3 | 107.48 (12) |
N1—Zn1—Cl2 | 114.06 (15) | N3—Zn2—Cl3 | 113.43 (14) |
O1—Zn1—Cl1 | 110.63 (14) | O3—Zn2—Cl4 | 110.55 (14) |
N1—Zn1—Cl1 | 109.73 (14) | N3—Zn2—Cl4 | 111.53 (13) |
Cl2—Zn1—Cl1 | 116.43 (6) | Cl3—Zn2—Cl4 | 115.33 (6) |
C2—O1—Zn1 | 123.6 (3) | C15—O3—Zn2 | 123.1 (3) |
C4—O2—C13 | 118.2 (6) | C17—O4—C26 | 118.0 (6) |
C7—N1—C8 | 118.9 (5) | C20—N3—C21 | 118.6 (5) |
C7—N1—Zn1 | 119.1 (4) | C20—N3—Zn2 | 119.2 (4) |
C8—N1—Zn1 | 122.0 (4) | C21—N3—Zn2 | 122.2 (4) |
C10—N2—C9 | 117.6 (5) | C22—N4—C23 | 116.8 (4) |
C10—N2—H2A | 107.9 | C22—N4—H4A | 108.1 |
C9—N2—H2A | 107.8 | C23—N4—H4A | 108.2 |
C10—N2—H2B | 107.9 | C22—N4—H4B | 108.1 |
C9—N2—H2B | 107.9 | C23—N4—H4B | 108.1 |
H2A—N2—H2B | 107.2 | H4A—N4—H4B | 107.3 |
C6—C1—C7 | 117.8 (5) | C19—C14—C20 | 115.8 (6) |
C6—C1—C2 | 116.7 (6) | C19—C14—C15 | 117.8 (6) |
C7—C1—C2 | 125.5 (5) | C20—C14—C15 | 126.3 (5) |
O1—C2—C3 | 119.7 (5) | O3—C15—C16 | 119.6 (5) |
O1—C2—C1 | 122.5 (5) | O3—C15—C14 | 123.4 (5) |
C3—C2—C1 | 117.8 (5) | C16—C15—C14 | 117.0 (5) |
C4—C3—C2 | 122.1 (6) | C17—C16—C15 | 123.2 (6) |
C4—C3—H3 | 118.9 | C17—C16—H16 | 118.4 |
C2—C3—H3 | 118.9 | C15—C16—H16 | 118.4 |
C3—C4—O2 | 114.2 (6) | C16—C17—O4 | 114.8 (6) |
C3—C4—C5 | 121.9 (6) | C16—C17—C18 | 120.7 (6) |
O2—C4—C5 | 123.9 (6) | O4—C17—C18 | 124.5 (6) |
C6—C5—C4 | 116.9 (6) | C19—C18—C17 | 118.4 (6) |
C6—C5—H5 | 121.6 | C19—C18—H18 | 120.8 |
C4—C5—H5 | 121.6 | C17—C18—H18 | 120.8 |
C5—C6—C1 | 124.6 (6) | C18—C19—C14 | 122.9 (6) |
C5—C6—H6 | 117.7 | C18—C19—H19 | 118.5 |
C1—C6—H6 | 117.7 | C14—C19—H19 | 118.5 |
N1—C7—C1 | 129.1 (5) | N3—C20—C14 | 127.6 (6) |
N1—C7—H7 | 115.5 | N3—C20—H20 | 116.2 |
C1—C7—H7 | 115.5 | C14—C20—H20 | 116.2 |
N1—C8—C9 | 112.8 (5) | N3—C21—C22 | 113.5 (5) |
N1—C8—H8A | 109.0 | N3—C21—H21A | 108.9 |
C9—C8—H8A | 109.0 | C22—C21—H21A | 108.9 |
N1—C8—H8B | 109.0 | N3—C21—H21B | 108.9 |
C9—C8—H8B | 109.0 | C22—C21—H21B | 108.9 |
H8A—C8—H8B | 107.8 | H21A—C21—H21B | 107.7 |
C8—C9—N2 | 112.9 (5) | N4—C22—C21 | 111.8 (5) |
C8—C9—H9A | 109.0 | N4—C22—H22A | 109.3 |
N2—C9—H9A | 109.0 | C21—C22—H22A | 109.3 |
C8—C9—H9B | 109.0 | N4—C22—H22B | 109.3 |
N2—C9—H9B | 109.0 | C21—C22—H22B | 109.3 |
H9A—C9—H9B | 107.8 | H22A—C22—H22B | 107.9 |
C12—C10—N2 | 112.0 (6) | C25—C23—C24 | 112.7 (6) |
C12—C10—C11 | 113.4 (7) | C25—C23—N4 | 112.8 (6) |
N2—C10—C11 | 110.1 (6) | C24—C23—N4 | 109.3 (6) |
C12—C10—H10 | 107.0 | C25—C23—H23 | 107.3 |
N2—C10—H10 | 107.0 | C24—C23—H23 | 107.3 |
C11—C10—H10 | 107.0 | N4—C23—H23 | 107.3 |
C10—C11—H11A | 109.5 | C23—C24—H24A | 109.5 |
C10—C11—H11B | 109.5 | C23—C24—H24B | 109.5 |
H11A—C11—H11B | 109.5 | H24A—C24—H24B | 109.5 |
C10—C11—H11C | 109.5 | C23—C24—H24C | 109.5 |
H11A—C11—H11C | 109.5 | H24A—C24—H24C | 109.5 |
H11B—C11—H11C | 109.5 | H24B—C24—H24C | 109.5 |
C10—C12—H12A | 109.5 | C23—C25—H25A | 109.5 |
C10—C12—H12B | 109.5 | C23—C25—H25B | 109.5 |
H12A—C12—H12B | 109.5 | H25A—C25—H25B | 109.5 |
C10—C12—H12C | 109.5 | C23—C25—H25C | 109.5 |
H12A—C12—H12C | 109.5 | H25A—C25—H25C | 109.5 |
H12B—C12—H12C | 109.5 | H25B—C25—H25C | 109.5 |
O2—C13—H13A | 109.5 | O4—C26—H26A | 109.5 |
O2—C13—H13B | 109.5 | O4—C26—H26B | 109.5 |
H13A—C13—H13B | 109.5 | H26A—C26—H26B | 109.5 |
O2—C13—H13C | 109.5 | O4—C26—H26C | 109.5 |
H13A—C13—H13C | 109.5 | H26A—C26—H26C | 109.5 |
H13B—C13—H13C | 109.5 | H26B—C26—H26C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4B···O1i | 0.90 | 2.03 | 2.904 (6) | 163 |
N4—H4A···Cl2i | 0.90 | 2.73 | 3.466 (5) | 140 |
N2—H2B···Cl3 | 0.90 | 2.74 | 3.484 (5) | 140 |
N2—H2A···O3 | 0.90 | 2.03 | 2.892 (6) | 161 |
Symmetry code: (i) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | [ZnCl2(C13H20N2O2)] |
Mr | 372.58 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 6.491 (3), 12.351 (2), 22.803 (3) |
α, β, γ (°) | 90.707 (2), 96.201 (2), 90.660 (2) |
V (Å3) | 1817.1 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.65 |
Crystal size (mm) | 0.13 × 0.10 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.814, 0.880 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8230, 5775, 4093 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.181, 1.08 |
No. of reflections | 5775 |
No. of parameters | 367 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.63, −0.57 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008) and local programs.
Zn1—O1 | 1.995 (4) | Zn2—O3 | 1.994 (4) |
Zn1—N1 | 2.061 (4) | Zn2—N3 | 2.095 (5) |
Zn1—Cl2 | 2.3252 (18) | Zn2—Cl3 | 2.2994 (16) |
Zn1—Cl1 | 2.3628 (17) | Zn2—Cl4 | 2.3575 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4B···O1i | 0.90 | 2.03 | 2.904 (6) | 162.6 |
N4—H4A···Cl2i | 0.90 | 2.73 | 3.466 (5) | 140.3 |
N2—H2B···Cl3 | 0.90 | 2.74 | 3.484 (5) | 140.4 |
N2—H2A···O3 | 0.90 | 2.03 | 2.892 (6) | 160.9 |
Symmetry code: (i) x, y−1, z. |
References
Ali, H. M., Mohamed Mustafa, M. I., Rizal, M. R. & Ng, S. W. (2008). Acta Cryst. E64, m718–m719. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Granifo, J., Garland, M. T. & Baggio, R. (2006). Acta Cryst. C62, m56–m59. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Han, Z.-Q., Wang, Y. & Han, S. (2010). Acta Cryst. E66, m469. Web of Science CrossRef IUCr Journals Google Scholar
Munro, O. Q., Gillham, K. & Akerman, M. P. (2009). Acta Cryst. C65, m317–m320. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, S.-X. (2007). Acta Cryst. E63, m706–m707. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhu, X.-W. (2008). Acta Cryst. E64, m1456–m1457. Web of Science CrossRef IUCr Journals Google Scholar
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The structures of zinc complexes with Schiff bases have received a great deal of attention (Munro et al., 2009; Granifo et al., 2006). The title compound was first reported in the monoclinic space group P21/n (Han et al., 2010). The author reports here a triclinic modification, I, in the space group P -1 with an asymmetric unit that contains two independent mononuclear zinc complex molecules (Fig. 1). In each molecule the Zn atoms are coordinated in a bidentate fashion by phenolate O and imine N atoms of the Schiff base ligand. Two Cl- anions complete the tetrahedral coordination sphere in each case. The Zn1–O1, 1.995 (4)Å, Zn2–O3, 1.994 (4) Å, Zn1–N1, 2.061 (3)Å, Zn2–N3, 2.095 (3)Å, Zn1–Cl1, 2.3268, Zn1–Cl2, 2.3252 (18), Zn2–Cl3 2.2994 (16) and Zn2 Cl4 2.3575 (16) bond distances in the two independent molecules are comparable to one another but are generally longer than those observed in the monoclinic polymorph. This has Zn–O, 1.9425 (19) Å, Zn–N, 1.997 (2) Zn–Cl1 2.2554 (10) and Zn–Cl2, 2.2290 (9)Å. The bond lengths in I are also longer than those reported in other zinc Schiff base complexes (Ali et al., 2008; Zhu, 2008; Wang, 2007). These differences may be due to packing effects. In the crystal, molecules are linked through N—H···O and N—H···Cl hydrogen bonds (Table 2), to form chains along the b axis (Fig. 2).