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The title compound, [Cu(C13H9NO2)(C15H11N3)], was prepared by direct reaction of the ligands with copper(II) salts in methanol solution. The air-stable compound crystallizes in the mononclinic space group C2/c. Although the imine portion of the chelate is disordered over a twofold axis, the copper environment is well defined as a meridionally substituted, tetragonally distorted octahedron.
Supporting information
CCDC reference: 189867
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- Disorder in main residue
- R factor = 0.045
- wR factor = 0.105
- Data-to-parameter ratio = 11.7
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: XSCANS/P4 (Siemens, 1994); cell refinement: XSCANS/P4; data reduction: XSCANS/P4; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
Crystal data top
[Cu(C13H9NO2)(C15H11N3)] | F(000) = 1044 |
Mr = 508.02 | Dx = 1.482 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 20 reflections |
a = 17.132 (3) Å | θ = 1.5–22.5° |
b = 13.918 (3) Å | µ = 0.99 mm−1 |
c = 9.793 (2) Å | T = 293 K |
β = 102.87 (3)° | Rhomb, dark green |
V = 2276.5 (8) Å3 | 0.5 × 0.3 × 0.3 mm |
Z = 4 | |
Data collection top
Siemens P4 diffractometer | 1395 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 25.0°, θmin = 1.9° |
ω scans | h = −20→1 |
Absorption correction: ψ scan (XSCANS/P4; Siemens, 1994) | k = −1→16 |
Tmin = 0.666, Tmax = 0.743 | l = −11→11 |
2417 measured reflections | 3 standard reflections every 47 reflections |
1997 independent reflections | intensity decay: none |
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) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0421P)2 + 0.7221P] where P = (Fo2 + 2Fc2)/3 |
1997 reflections | (Δ/σ)max < 0.001 |
171 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
Special details top
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 | Uiso*/Ueq | Occ. (<1) |
Cu1 | 1.0000 | 0.21678 (5) | 0.2500 | 0.0441 (2) | |
O1 | 1.07961 (17) | 0.2199 (2) | 0.1352 (3) | 0.0660 (8) | |
N1 | 1.0194 (3) | 0.3559 (4) | 0.2259 (6) | 0.0321 (14) | 0.50 |
N2 | 0.90201 (19) | 0.1705 (2) | 0.0544 (3) | 0.0511 (8) | |
N3 | 1.0000 | 0.0664 (3) | 0.2500 | 0.0364 (9) | |
C1 | 0.9833 (5) | 0.4226 (6) | 0.2780 (8) | 0.040 (2) | 0.50 |
C2 | 1.0718 (2) | 0.3912 (3) | 0.1335 (4) | 0.0540 (11) | |
C3 | 1.0972 (3) | 0.4770 (3) | 0.0845 (4) | 0.0665 (12) | |
C4 | 1.1476 (3) | 0.4795 (3) | −0.0064 (4) | 0.0610 (11) | |
C5 | 1.1735 (2) | 0.3934 (3) | −0.0502 (4) | 0.0537 (10) | |
C6 | 1.1509 (2) | 0.3075 (3) | −0.0033 (4) | 0.0487 (10) | |
C7 | 1.0995 (2) | 0.3028 (3) | 0.0908 (4) | 0.0483 (10) | |
C8 | 0.8528 (3) | 0.2267 (3) | −0.0395 (4) | 0.0654 (11) | |
C9 | 0.8014 (3) | 0.1907 (4) | −0.1551 (5) | 0.0735 (14) | |
C10 | 0.8004 (3) | 0.0947 (4) | −0.1774 (4) | 0.0713 (13) | |
C11 | 0.8498 (3) | 0.0351 (3) | −0.0835 (4) | 0.0613 (11) | |
C12 | 0.8997 (2) | 0.0764 (3) | 0.0335 (3) | 0.0424 (9) | |
C13 | 0.9529 (2) | 0.0178 (2) | 0.1433 (3) | 0.0400 (8) | |
C14 | 0.9540 (2) | −0.0821 (3) | 0.1398 (4) | 0.0540 (10) | |
C15 | 1.0000 | −0.1315 (4) | 0.2500 | 0.0597 (16) | |
H1 | 1.0000 | 0.490 (5) | 0.2500 | 0.09 (2)* | |
H3A | 1.0794 | 0.5347 | 0.1145 | 0.080* | |
H4A | 1.1640 | 0.5377 | −0.0376 | 0.073* | |
H5A | 1.2070 | 0.3938 | −0.1130 | 0.064* | |
H6A | 1.1698 | 0.2507 | −0.0342 | 0.058* | |
H8A | 0.8540 | 0.2928 | −0.0248 | 0.078* | |
H9A | 0.7678 | 0.2313 | −0.2173 | 0.088* | |
H10A | 0.7662 | 0.0689 | −0.2561 | 0.086* | |
H11A | 0.8498 | −0.0309 | −0.0981 | 0.074* | |
H14A | 0.9239 | −0.1150 | 0.0633 | 0.065* | |
H15A | 1.0000 | −0.1983 | 0.2500 | 0.072* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0617 (5) | 0.0313 (4) | 0.0410 (4) | 0.000 | 0.0147 (3) | 0.000 |
O1 | 0.081 (2) | 0.0681 (18) | 0.0540 (16) | −0.0311 (17) | 0.0270 (15) | −0.0001 (15) |
N1 | 0.032 (4) | 0.027 (3) | 0.038 (4) | 0.005 (3) | 0.009 (3) | −0.004 (3) |
N2 | 0.057 (2) | 0.0481 (19) | 0.0461 (18) | 0.0051 (17) | 0.0082 (16) | −0.0014 (16) |
N3 | 0.041 (2) | 0.033 (2) | 0.037 (2) | 0.000 | 0.013 (2) | 0.000 |
C1 | 0.046 (6) | 0.033 (4) | 0.038 (6) | 0.000 (4) | 0.007 (3) | −0.002 (4) |
C2 | 0.036 (2) | 0.089 (3) | 0.036 (2) | −0.003 (2) | 0.0064 (17) | 0.003 (2) |
C3 | 0.065 (3) | 0.068 (3) | 0.065 (3) | 0.027 (2) | 0.012 (2) | −0.003 (2) |
C4 | 0.068 (3) | 0.051 (3) | 0.066 (3) | 0.005 (2) | 0.019 (2) | 0.012 (2) |
C5 | 0.057 (2) | 0.056 (3) | 0.055 (2) | −0.007 (2) | 0.025 (2) | 0.0011 (19) |
C6 | 0.052 (2) | 0.049 (3) | 0.049 (2) | −0.0091 (18) | 0.0178 (19) | −0.0062 (17) |
C7 | 0.045 (2) | 0.065 (3) | 0.0341 (19) | −0.0160 (19) | 0.0061 (17) | −0.0010 (18) |
C8 | 0.071 (3) | 0.065 (3) | 0.055 (3) | 0.009 (2) | 0.005 (2) | 0.003 (2) |
C9 | 0.062 (3) | 0.099 (4) | 0.055 (3) | 0.003 (3) | 0.005 (2) | 0.014 (3) |
C10 | 0.057 (3) | 0.106 (4) | 0.047 (2) | −0.023 (3) | 0.003 (2) | 0.001 (3) |
C11 | 0.063 (3) | 0.068 (3) | 0.053 (2) | −0.026 (2) | 0.013 (2) | −0.006 (2) |
C12 | 0.041 (2) | 0.050 (2) | 0.039 (2) | −0.0088 (18) | 0.0153 (17) | −0.0026 (18) |
C13 | 0.048 (2) | 0.0360 (19) | 0.041 (2) | −0.0067 (17) | 0.0203 (18) | −0.0048 (16) |
C14 | 0.068 (3) | 0.041 (2) | 0.060 (2) | −0.014 (2) | 0.030 (2) | −0.0104 (19) |
C15 | 0.076 (4) | 0.030 (3) | 0.082 (4) | 0.000 | 0.038 (4) | 0.000 |
Geometric parameters (Å, º) top
Cu1—O1 | 1.952 (3) | C5—C6 | 1.369 (5) |
Cu1—N1 | 1.987 (5) | C5—H5A | 0.930 |
Cu1—N3 | 2.093 (4) | C6—C7 | 1.410 (5) |
Cu1—N2 | 2.339 (3) | C6—H6A | 0.930 |
O1—C7 | 1.305 (4) | C8—C9 | 1.366 (6) |
N1—C1 | 1.283 (7) | C8—H8A | 0.930 |
N1—C2 | 1.493 (6) | C9—C10 | 1.353 (6) |
C1—H1 | 1.04 (6) | C9—H9A | 0.930 |
N2—C12 | 1.326 (5) | C10—C11 | 1.380 (6) |
N2—C8 | 1.350 (5) | C10—H10A | 0.930 |
N3—C13 | 1.351 (4) | C11—C12 | 1.392 (5) |
C2—C3 | 1.393 (6) | C11—H11A | 0.930 |
C2—C7 | 1.416 (5) | C12—C13 | 1.488 (5) |
C3—C4 | 1.372 (5) | C13—C14 | 1.391 (5) |
C3—H3A | 0.930 | C14—C15 | 1.371 (5) |
C4—C5 | 1.378 (5) | C14—H14A | 0.930 |
C4—H4A | 0.930 | C15—H15A | 0.930 |
| | | |
O1—Cu1—O1i | 177.48 (18) | C2—C3—H3A | 118.8 |
O1—Cu1—N1i | 101.73 (16) | C3—C4—C5 | 118.2 (4) |
O1i—Cu1—N1i | 75.75 (16) | C3—C4—H4A | 120.9 |
O1—Cu1—N1 | 75.75 (16) | C5—C4—H4A | 120.9 |
O1i—Cu1—N1 | 101.73 (16) | C6—C5—C4 | 121.3 (4) |
O1—Cu1—N3 | 91.26 (9) | C6—C5—H5A | 119.3 |
O1—Cu1—N2 | 90.03 (11) | C4—C5—H5A | 119.3 |
N1—Cu1—N2 | 106.2 (2) | C5—C6—C7 | 121.7 (3) |
N3—Cu1—N2 | 74.02 (8) | C5—C6—H6A | 119.2 |
O1—Cu1—N2i | 90.67 (11) | C7—C6—H6A | 119.2 |
N1—Cu1—N2i | 104.9 (2) | O1—C7—C6 | 120.4 (4) |
N3—Cu1—N2i | 74.02 (8) | O1—C7—C2 | 122.7 (4) |
N2—Cu1—N2i | 148.03 (16) | C6—C7—C2 | 116.9 (3) |
C7—O1—Cu1 | 118.6 (3) | N2—C8—C9 | 122.8 (4) |
C1—N1—C2 | 114.3 (5) | N2—C8—H8A | 118.6 |
C1i—N1—Cu1 | 165.9 (7) | C9—C8—H8A | 118.6 |
C1—N1—Cu1 | 123.4 (4) | C10—C9—C8 | 118.6 (4) |
C2—N1—Cu1 | 122.1 (3) | C10—C9—H9A | 120.7 |
C1i—C1—C2i | 162.8 (3) | C8—C9—H9A | 120.7 |
N1i—C1—C2i | 72.4 (6) | C9—C10—C11 | 120.2 (4) |
N1—C1—C2i | 116.4 (6) | C9—C10—H10A | 119.9 |
C1i—C1—H1 | 64.9 (17) | C11—C10—H10A | 119.9 |
N1i—C1—H1 | 155.1 (19) | C10—C11—C12 | 118.3 (4) |
N1—C1—H1 | 111.4 (18) | C10—C11—H11A | 120.9 |
C2i—C1—H1 | 132.2 (17) | C12—C11—H11A | 120.9 |
C12—N2—C8 | 118.3 (4) | N2—C12—C11 | 121.8 (4) |
C12—N2—Cu1 | 113.0 (2) | N2—C12—C13 | 115.9 (3) |
C8—N2—Cu1 | 128.6 (3) | C11—C12—C13 | 122.3 (4) |
C13—N3—C13i | 119.9 (4) | N3—C13—C14 | 120.7 (4) |
C13—N3—Cu1 | 120.1 (2) | N3—C13—C12 | 116.7 (3) |
C13i—N3—Cu1 | 120.1 (2) | C14—C13—C12 | 122.7 (3) |
C3—C2—C7 | 119.5 (3) | C15—C14—C13 | 119.4 (4) |
C3—C2—C1i | 103.7 (4) | C15—C14—H14A | 120.3 |
C7—C2—C1i | 136.8 (4) | C13—C14—H14A | 120.3 |
C3—C2—N1 | 140.1 (4) | C14i—C15—C14 | 119.8 (5) |
C7—C2—N1 | 100.4 (4) | C14i—C15—H15A | 120.1 |
C4—C3—C2 | 122.4 (4) | C14—C15—H15A | 120.1 |
C4—C3—H3A | 118.8 | | |
Symmetry code: (i) −x+2, y, −z+1/2. |
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