metal-organic compounds
(2,2′-Bipyridine-κ2N,N′)[N-(2-oxido-1-naphthylidene)threoninato-κ3O1,N,O2]copper(II)
aSchool of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
*Correspondence e-mail: lilianzhi1963@yahoo.com.cn
In the title complex, [Cu(C15H13NO4)(C10H8N2)], the Schiff base ligand is derived from the condensation of 2-hydroxy-1-naphthaldehyde and L-threonine. The CuII atom is five-coordinated by one N atom and two O atoms from the Schiff base ligand and by two N atoms from a 2,2′-bipyridine ligand in a distorted square-pyramidal geometry. In the the combination of intermolecular O—H⋯O and C—H⋯O hydrogen bonds leads to a two-dimensional network.
Related literature
For related literature, see: Garnovski et al. (1993); Kalagouda et al. (2006); Wang et al. (1999).
Experimental
Crystal data
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Data collection: SMART (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536808012191/hy2129sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808012191/hy2129Isup2.hkl
L-Threonine (0.119 g, 1 mmol) was dissolved in hot methanol (10 ml), which was then added to a methanol solution (3 ml) of 2-hydroxy-1-naphthaldehyde (0.172 g, 1 mmol). The mixture was stirred at 323 K for 2 h. Subsequently, an aqueous solution (2 ml) of cupric acetate monohydrate (0.200 g, 1 mmol) was added dropwise and stirred for 2 h. A methanol solution (5 ml) of 2,2'-bipyridine (0.156 g, 1 mmol) was added dropwise and stirred for 4 h. The solution was held at room temperature for 10 d and blue block crystals suitable for X-ray diffraction were obtained.
H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic), 0.98(CH) and 0.96(CH3) Å, and O—H = 0.82 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C,O) for methyl and hydroxyl groups.
Data collection: SMART (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[Cu(C15H13NO4)(C10H8N2)] | F(000) = 1012 |
Mr = 490.99 | Dx = 1.459 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5604 reflections |
a = 9.955 (2) Å | θ = 2.3–26.1° |
b = 12.180 (3) Å | µ = 1.01 mm−1 |
c = 18.438 (4) Å | T = 298 K |
V = 2235.6 (9) Å3 | Block, blue |
Z = 4 | 0.29 × 0.28 × 0.16 mm |
Bruker SMART APEX CCD area-detector diffractometer | 5278 independent reflections |
Radiation source: fine-focus sealed tube | 4243 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ϕ and ω scans | θmax = 28.3°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.757, Tmax = 0.855 | k = −14→16 |
14242 measured reflections | l = −20→24 |
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)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.0472P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
5278 reflections | Δρmax = 0.32 e Å−3 |
300 parameters | Δρmin = −0.54 e Å−3 |
492 restraints | Absolute structure: Flack (1983), 2229 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.005 (13) |
[Cu(C15H13NO4)(C10H8N2)] | V = 2235.6 (9) Å3 |
Mr = 490.99 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 9.955 (2) Å | µ = 1.01 mm−1 |
b = 12.180 (3) Å | T = 298 K |
c = 18.438 (4) Å | 0.29 × 0.28 × 0.16 mm |
Bruker SMART APEX CCD area-detector diffractometer | 5278 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4243 reflections with I > 2σ(I) |
Tmin = 0.757, Tmax = 0.855 | Rint = 0.027 |
14242 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.089 | Δρmax = 0.32 e Å−3 |
S = 1.04 | Δρmin = −0.54 e Å−3 |
5278 reflections | Absolute structure: Flack (1983), 2229 Friedel pairs |
300 parameters | Absolute structure parameter: −0.005 (13) |
492 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.32501 (3) | 1.00767 (2) | 0.977106 (17) | 0.03806 (10) | |
N1 | 0.1622 (2) | 1.08781 (15) | 0.95744 (11) | 0.0313 (4) | |
N2 | 0.2672 (3) | 0.89079 (19) | 1.06492 (15) | 0.0491 (6) | |
N3 | 0.5005 (2) | 0.93672 (19) | 1.00252 (14) | 0.0480 (6) | |
O4 | 0.3191 (2) | 0.93362 (17) | 0.88490 (11) | 0.0498 (5) | |
O2 | 0.29386 (19) | 1.31490 (16) | 1.05070 (12) | 0.0512 (5) | |
O1 | 0.37076 (18) | 1.14608 (15) | 1.03256 (11) | 0.0424 (4) | |
O3 | −0.05190 (19) | 1.07490 (16) | 1.05400 (12) | 0.0474 (5) | |
H3 | −0.0961 | 1.1082 | 1.0236 | 0.071* | |
C1 | 0.2783 (3) | 1.2178 (2) | 1.03223 (14) | 0.0371 (6) | |
C2 | 0.1394 (3) | 1.17825 (19) | 1.00763 (13) | 0.0319 (5) | |
H28 | 0.0912 | 1.2379 | 0.9832 | 0.038* | |
C3 | 0.0596 (3) | 1.1395 (2) | 1.07501 (15) | 0.0368 (6) | |
H29 | 0.1194 | 1.0925 | 1.1037 | 0.044* | |
C4 | 0.0177 (3) | 1.2351 (3) | 1.12313 (16) | 0.0510 (7) | |
H21A | −0.0285 | 1.2076 | 1.1651 | 0.077* | |
H21B | −0.0409 | 1.2830 | 1.0965 | 0.077* | |
H21C | 0.0960 | 1.2750 | 1.1382 | 0.077* | |
C5 | 0.0856 (2) | 1.0765 (2) | 0.90139 (14) | 0.0325 (5) | |
H11 | 0.0125 | 1.1237 | 0.8978 | 0.039* | |
C6 | 0.1028 (2) | 0.9982 (2) | 0.84450 (12) | 0.0363 (5) | |
C7 | 0.2228 (3) | 0.9366 (2) | 0.83774 (15) | 0.0415 (6) | |
C8 | 0.2402 (3) | 0.8722 (3) | 0.77391 (16) | 0.0545 (8) | |
H18 | 0.3199 | 0.8335 | 0.7678 | 0.065* | |
C9 | 0.1453 (4) | 0.8654 (3) | 0.72205 (16) | 0.0560 (8) | |
H19 | 0.1615 | 0.8224 | 0.6813 | 0.067* | |
C10 | 0.0215 (3) | 0.9221 (2) | 0.72803 (15) | 0.0452 (6) | |
C11 | −0.0016 (3) | 0.9893 (2) | 0.78988 (13) | 0.0397 (6) | |
C12 | −0.1269 (3) | 1.0408 (2) | 0.79527 (17) | 0.0495 (7) | |
H27 | −0.1453 | 1.0845 | 0.8354 | 0.059* | |
C13 | −0.2234 (4) | 1.0284 (3) | 0.74247 (19) | 0.0588 (8) | |
H26 | −0.3055 | 1.0640 | 0.7475 | 0.071* | |
C14 | −0.2000 (4) | 0.9635 (3) | 0.68174 (18) | 0.0621 (9) | |
H25 | −0.2659 | 0.9556 | 0.6464 | 0.074* | |
C15 | −0.0795 (4) | 0.9115 (3) | 0.67446 (17) | 0.0572 (8) | |
H15 | −0.0634 | 0.8685 | 0.6337 | 0.069* | |
C16 | 0.1466 (4) | 0.8711 (3) | 1.0941 (2) | 0.0660 (9) | |
H17 | 0.0701 | 0.8976 | 1.0710 | 0.079* | |
C17 | 0.1333 (6) | 0.8119 (3) | 1.1577 (3) | 0.0965 (13) | |
H22 | 0.0488 | 0.7999 | 1.1777 | 0.116* | |
C18 | 0.2463 (6) | 0.7710 (4) | 1.1912 (3) | 0.1063 (14) | |
H36 | 0.2387 | 0.7302 | 1.2336 | 0.128* | |
C19 | 0.3693 (5) | 0.7909 (3) | 1.1617 (3) | 0.0883 (12) | |
H37 | 0.4468 | 0.7665 | 1.1849 | 0.106* | |
C20 | 0.3776 (4) | 0.8483 (2) | 1.09632 (19) | 0.0579 (8) | |
C21 | 0.5052 (3) | 0.8664 (2) | 1.05811 (19) | 0.0524 (7) | |
C22 | 0.6242 (4) | 0.8126 (3) | 1.0751 (2) | 0.0701 (10) | |
H33 | 0.6271 | 0.7624 | 1.1131 | 0.084* | |
C23 | 0.7371 (4) | 0.8343 (3) | 1.0354 (3) | 0.0775 (11) | |
H23 | 0.8169 | 0.7986 | 1.0468 | 0.093* | |
C24 | 0.7348 (3) | 0.9067 (3) | 0.9799 (3) | 0.0719 (10) | |
H24 | 0.8118 | 0.9222 | 0.9532 | 0.086* | |
C25 | 0.6136 (3) | 0.9570 (3) | 0.9642 (2) | 0.0634 (9) | |
H32 | 0.6097 | 1.0066 | 0.9259 | 0.076* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.03383 (16) | 0.04027 (16) | 0.04008 (17) | 0.00393 (14) | −0.00421 (14) | 0.00230 (15) |
N1 | 0.0301 (10) | 0.0347 (10) | 0.0291 (11) | 0.0002 (9) | 0.0011 (9) | −0.0009 (8) |
N2 | 0.0536 (15) | 0.0405 (13) | 0.0531 (16) | −0.0017 (11) | −0.0030 (13) | 0.0083 (12) |
N3 | 0.0409 (13) | 0.0384 (13) | 0.0647 (17) | 0.0035 (10) | −0.0093 (12) | 0.0003 (11) |
O4 | 0.0456 (11) | 0.0590 (12) | 0.0448 (12) | 0.0165 (10) | −0.0016 (11) | −0.0084 (9) |
O2 | 0.0434 (11) | 0.0466 (11) | 0.0636 (14) | −0.0096 (9) | 0.0033 (10) | −0.0158 (10) |
O1 | 0.0341 (9) | 0.0460 (10) | 0.0470 (12) | −0.0025 (8) | −0.0092 (9) | −0.0015 (9) |
O3 | 0.0356 (10) | 0.0553 (12) | 0.0514 (13) | −0.0103 (9) | 0.0020 (9) | 0.0047 (10) |
C1 | 0.0398 (13) | 0.0424 (13) | 0.0291 (13) | −0.0075 (11) | 0.0053 (11) | −0.0008 (11) |
C2 | 0.0348 (12) | 0.0333 (12) | 0.0275 (12) | 0.0016 (10) | −0.0021 (10) | −0.0008 (9) |
C3 | 0.0339 (13) | 0.0442 (14) | 0.0323 (13) | −0.0029 (11) | 0.0013 (11) | 0.0017 (11) |
C4 | 0.0536 (18) | 0.0621 (19) | 0.0374 (15) | 0.0016 (15) | 0.0060 (14) | −0.0050 (14) |
C5 | 0.0326 (12) | 0.0360 (12) | 0.0288 (12) | 0.0016 (10) | −0.0001 (10) | 0.0002 (10) |
C6 | 0.0456 (13) | 0.0364 (12) | 0.0270 (11) | 0.0003 (13) | 0.0012 (10) | −0.0009 (11) |
C7 | 0.0486 (15) | 0.0413 (14) | 0.0346 (14) | 0.0009 (12) | 0.0065 (12) | −0.0036 (11) |
C8 | 0.0637 (19) | 0.0570 (17) | 0.0428 (17) | 0.0105 (15) | 0.0104 (15) | −0.0090 (14) |
C9 | 0.074 (2) | 0.0580 (16) | 0.0354 (15) | −0.0053 (16) | 0.0078 (15) | −0.0131 (13) |
C10 | 0.0586 (16) | 0.0469 (15) | 0.0299 (13) | −0.0123 (13) | 0.0007 (13) | −0.0025 (11) |
C11 | 0.0510 (14) | 0.0392 (13) | 0.0291 (11) | −0.0082 (13) | −0.0017 (11) | 0.0002 (11) |
C12 | 0.0552 (16) | 0.0542 (15) | 0.0392 (15) | −0.0003 (13) | −0.0115 (13) | −0.0065 (12) |
C13 | 0.0596 (17) | 0.065 (2) | 0.0515 (17) | −0.0031 (15) | −0.0187 (15) | −0.0011 (15) |
C14 | 0.076 (2) | 0.0662 (18) | 0.0440 (16) | −0.0210 (16) | −0.0221 (16) | 0.0030 (14) |
C15 | 0.079 (2) | 0.0582 (17) | 0.0344 (15) | −0.0206 (16) | −0.0067 (15) | −0.0039 (13) |
C16 | 0.074 (2) | 0.0503 (17) | 0.074 (2) | −0.0007 (16) | 0.0131 (19) | 0.0167 (16) |
C17 | 0.104 (3) | 0.085 (3) | 0.101 (3) | 0.002 (2) | 0.034 (3) | 0.038 (2) |
C18 | 0.128 (3) | 0.098 (3) | 0.092 (3) | 0.009 (3) | 0.010 (3) | 0.049 (2) |
C19 | 0.100 (3) | 0.080 (2) | 0.084 (2) | 0.015 (2) | −0.007 (2) | 0.035 (2) |
C20 | 0.0753 (19) | 0.0387 (14) | 0.0597 (18) | 0.0037 (15) | −0.0113 (17) | 0.0086 (14) |
C21 | 0.0575 (17) | 0.0352 (14) | 0.0645 (18) | 0.0071 (13) | −0.0215 (15) | −0.0033 (14) |
C22 | 0.076 (2) | 0.0502 (17) | 0.084 (2) | 0.0146 (17) | −0.029 (2) | −0.0012 (17) |
C23 | 0.060 (2) | 0.063 (2) | 0.109 (3) | 0.0182 (17) | −0.031 (2) | −0.020 (2) |
C24 | 0.0489 (17) | 0.0566 (18) | 0.110 (3) | 0.0058 (15) | −0.010 (2) | −0.015 (2) |
C25 | 0.0492 (17) | 0.0481 (16) | 0.093 (2) | 0.0030 (13) | −0.0050 (18) | −0.0026 (16) |
Cu1—O4 | 1.925 (2) | C8—H18 | 0.9300 |
Cu1—N1 | 1.926 (2) | C9—C10 | 1.417 (5) |
Cu1—N3 | 2.005 (2) | C9—H19 | 0.9300 |
Cu1—O1 | 2.0236 (18) | C10—C15 | 1.415 (4) |
Cu1—N2 | 2.231 (3) | C10—C11 | 1.422 (4) |
N1—C5 | 1.292 (3) | C11—C12 | 1.400 (4) |
N1—C2 | 1.457 (3) | C12—C13 | 1.376 (4) |
N2—C16 | 1.338 (4) | C12—H27 | 0.9300 |
N2—C20 | 1.345 (4) | C13—C14 | 1.390 (5) |
N3—C21 | 1.337 (4) | C13—H26 | 0.9300 |
N3—C25 | 1.352 (4) | C14—C15 | 1.363 (5) |
O4—C7 | 1.295 (4) | C14—H25 | 0.9300 |
O2—C1 | 1.240 (3) | C15—H15 | 0.9300 |
O1—C1 | 1.269 (3) | C16—C17 | 1.384 (5) |
O3—C3 | 1.415 (3) | C16—H17 | 0.9300 |
O3—H3 | 0.8200 | C17—C18 | 1.376 (7) |
C1—C2 | 1.533 (4) | C17—H22 | 0.9300 |
C2—C3 | 1.548 (4) | C18—C19 | 1.362 (7) |
C2—H28 | 0.9800 | C18—H36 | 0.9300 |
C3—C4 | 1.522 (4) | C19—C20 | 1.397 (5) |
C3—H29 | 0.9800 | C19—H37 | 0.9300 |
C4—H21A | 0.9600 | C20—C21 | 1.469 (5) |
C4—H21B | 0.9600 | C21—C22 | 1.390 (5) |
C4—H21C | 0.9600 | C22—C23 | 1.366 (6) |
C5—C6 | 1.428 (3) | C22—H33 | 0.9300 |
C5—H11 | 0.9300 | C23—C24 | 1.352 (6) |
C6—C7 | 1.417 (4) | C23—H23 | 0.9300 |
C6—C11 | 1.452 (3) | C24—C25 | 1.384 (5) |
C7—C8 | 1.425 (4) | C24—H24 | 0.9300 |
C8—C9 | 1.346 (5) | C25—H32 | 0.9300 |
O4—Cu1—N1 | 92.62 (8) | C9—C8—H18 | 118.8 |
O4—Cu1—N3 | 91.77 (9) | C7—C8—H18 | 118.8 |
N1—Cu1—N3 | 174.65 (9) | C8—C9—C10 | 121.6 (3) |
O4—Cu1—O1 | 147.49 (9) | C8—C9—H19 | 119.2 |
N1—Cu1—O1 | 82.08 (8) | C10—C9—H19 | 119.2 |
N3—Cu1—O1 | 92.57 (9) | C15—C10—C9 | 121.3 (3) |
O4—Cu1—N2 | 109.51 (10) | C15—C10—C11 | 119.8 (3) |
N1—Cu1—N2 | 104.07 (9) | C9—C10—C11 | 118.9 (3) |
N3—Cu1—N2 | 77.29 (10) | C12—C11—C10 | 117.3 (3) |
O1—Cu1—N2 | 102.88 (9) | C12—C11—C6 | 123.7 (2) |
C5—N1—C2 | 119.8 (2) | C10—C11—C6 | 118.9 (3) |
C5—N1—Cu1 | 126.40 (17) | C13—C12—C11 | 121.5 (3) |
C2—N1—Cu1 | 113.27 (15) | C13—C12—H27 | 119.3 |
C16—N2—C20 | 119.4 (3) | C11—C12—H27 | 119.3 |
C16—N2—Cu1 | 129.6 (2) | C12—C13—C14 | 121.0 (3) |
C20—N2—Cu1 | 110.3 (2) | C12—C13—H26 | 119.5 |
C21—N3—C25 | 119.3 (3) | C14—C13—H26 | 119.5 |
C21—N3—Cu1 | 119.1 (2) | C15—C14—C13 | 119.4 (3) |
C25—N3—Cu1 | 121.6 (2) | C15—C14—H25 | 120.3 |
C7—O4—Cu1 | 127.02 (18) | C13—C14—H25 | 120.3 |
C1—O1—Cu1 | 114.08 (16) | C14—C15—C10 | 120.9 (3) |
C3—O3—H3 | 109.5 | C14—C15—H15 | 119.5 |
O2—C1—O1 | 124.4 (2) | C10—C15—H15 | 119.5 |
O2—C1—C2 | 119.6 (2) | N2—C16—C17 | 121.3 (4) |
O1—C1—C2 | 116.1 (2) | N2—C16—H17 | 119.3 |
N1—C2—C1 | 106.54 (19) | C17—C16—H17 | 119.3 |
N1—C2—C3 | 111.06 (19) | C18—C17—C16 | 119.4 (5) |
C1—C2—C3 | 108.7 (2) | C18—C17—H22 | 120.3 |
N1—C2—H28 | 110.1 | C16—C17—H22 | 120.3 |
C1—C2—H28 | 110.1 | C19—C18—C17 | 119.5 (4) |
C3—C2—H28 | 110.1 | C19—C18—H36 | 120.3 |
O3—C3—C4 | 111.7 (2) | C17—C18—H36 | 120.3 |
O3—C3—C2 | 110.6 (2) | C18—C19—C20 | 119.1 (4) |
C4—C3—C2 | 112.0 (2) | C18—C19—H37 | 120.4 |
O3—C3—H29 | 107.4 | C20—C19—H37 | 120.4 |
C4—C3—H29 | 107.4 | N2—C20—C19 | 121.1 (4) |
C2—C3—H29 | 107.4 | N2—C20—C21 | 116.2 (3) |
C3—C4—H21A | 109.5 | C19—C20—C21 | 122.7 (4) |
C3—C4—H21B | 109.5 | N3—C21—C22 | 120.3 (4) |
H21A—C4—H21B | 109.5 | N3—C21—C20 | 115.7 (3) |
C3—C4—H21C | 109.5 | C22—C21—C20 | 123.9 (3) |
H21A—C4—H21C | 109.5 | C23—C22—C21 | 119.3 (4) |
H21B—C4—H21C | 109.5 | C23—C22—H33 | 120.4 |
N1—C5—C6 | 126.0 (2) | C21—C22—H33 | 120.4 |
N1—C5—H11 | 117.0 | C24—C23—C22 | 121.2 (3) |
C6—C5—H11 | 117.0 | C24—C23—H23 | 119.4 |
C7—C6—C5 | 121.3 (2) | C22—C23—H23 | 119.4 |
C7—C6—C11 | 120.2 (2) | C23—C24—C25 | 117.5 (4) |
C5—C6—C11 | 118.3 (2) | C23—C24—H24 | 121.3 |
O4—C7—C6 | 125.5 (2) | C25—C24—H24 | 121.3 |
O4—C7—C8 | 116.7 (3) | N3—C25—C24 | 122.4 (4) |
C6—C7—C8 | 117.8 (3) | N3—C25—H32 | 118.8 |
C9—C8—C7 | 122.4 (3) | C24—C25—H32 | 118.8 |
C1—C2—C3—C4 | 71.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2i | 0.82 | 1.99 | 2.808 (3) | 178 |
C5—H11···O2i | 0.93 | 2.49 | 3.311 (3) | 147 |
C12—H27···O2i | 0.93 | 2.50 | 3.431 (4) | 174 |
C14—H25···O3ii | 0.93 | 2.52 | 3.445 (4) | 177 |
Symmetry codes: (i) x−1/2, −y+5/2, −z+2; (ii) −x−1/2, −y+2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C15H13NO4)(C10H8N2)] |
Mr | 490.99 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 298 |
a, b, c (Å) | 9.955 (2), 12.180 (3), 18.438 (4) |
V (Å3) | 2235.6 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.01 |
Crystal size (mm) | 0.29 × 0.28 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.757, 0.855 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14242, 5278, 4243 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.089, 1.04 |
No. of reflections | 5278 |
No. of parameters | 300 |
No. of restraints | 492 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.54 |
Absolute structure | Flack (1983), 2229 Friedel pairs |
Absolute structure parameter | −0.005 (13) |
Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Cu1—O4 | 1.925 (2) | Cu1—O1 | 2.0236 (18) |
Cu1—N1 | 1.926 (2) | Cu1—N2 | 2.231 (3) |
Cu1—N3 | 2.005 (2) | ||
O4—Cu1—N1 | 92.62 (8) | N3—Cu1—O1 | 92.57 (9) |
O4—Cu1—N3 | 91.77 (9) | O4—Cu1—N2 | 109.51 (10) |
N1—Cu1—N3 | 174.65 (9) | N1—Cu1—N2 | 104.07 (9) |
O4—Cu1—O1 | 147.49 (9) | N3—Cu1—N2 | 77.29 (10) |
N1—Cu1—O1 | 82.08 (8) | O1—Cu1—N2 | 102.88 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2i | 0.82 | 1.99 | 2.808 (3) | 178 |
C5—H11···O2i | 0.93 | 2.49 | 3.311 (3) | 147 |
C12—H27···O2i | 0.93 | 2.50 | 3.431 (4) | 174 |
C14—H25···O3ii | 0.93 | 2.52 | 3.445 (4) | 177 |
Symmetry codes: (i) x−1/2, −y+5/2, −z+2; (ii) −x−1/2, −y+2, z−1/2. |
Acknowledgements
The authors thank the Natural Science Foundation of Shandong Province (grant No. Y2004B02) for supporting this work.
References
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Amino acids and their derivatives are very important in molecular biology because of their roles in biochemical reactions. Schiff base complexes have continued to play the role of the most important stereochemical models in main group and transition metal coordination chemistry with their easy preparation and structural variation (Garnovski et al., 1993). So efforts have been made to synthesize and characterize amino Schiff base complexes with transition metals and more and more these new complexes have been reported (Kalagouda et al., 2006; Wang et al., 1999). Herein, we report the synthesis and crystal structure of a copper(II) complex with a tridentate Schiff base ligand derived from the condensation of 2-hydroxy-1-naphthaldehyde and L-threonine.
In the title compound (Fig. 1), the CuII atom is in a distorted square-pyramidal coordination geometry, defined by one N and two O atoms from the Schiff base ligand and two N atoms from a 2, 2'-bipyridine ligand. The Cu atom deviates from the basal equatorial plane (formed by O1, N1, O4 and N3) by 0.230 (2) Å toward N2 atom, with a significantly longer Cu1—N2 bond distance (Table 1). The Cu1—N2 bond deviates greatly from the right position to close the Cu1—N3 bond [the bond angle of N3—Cu1—N2 is 77.3 (1)°]. The bipyridine ligand deviates from planarity, with an angle of 11.7 (1)° between the two pyridyl rings. The least-square plane of the bipyridine ligand is approximately perpendicular to the basal equatorial plane [dihedral angle 100.3 (2)°]. In the crystal, the combination of intermolecular O—H···O and C—H···O hydrogen bonds (Table 2) leads to a two-dimensional network structure (Fig. 2).