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The asymmetric unit of the title compound, [Cu(C12H9O2)2], contains one half-molecule; the Cu atom lies on a centre of symmetry. The chelate ring is not planar and has a twist conformation. The dihedral angle between the naphthalene six-membered rings is 3.55 (3)°.
Supporting information
CCDC reference: 640369
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.006 Å
- R factor = 0.079
- wR factor = 0.218
- Data-to-parameter ratio = 18.8
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.100
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C1
PLAT412_ALERT_2_C Short Intra XH3 .. XHn H1C .. H4 .. 1.82 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C24 H18 Cu O4
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Bis(2-acetyl-1-naphtholato-
κ2O,
O')copper(II)
top
Crystal data top
[Cu(C12H9O2)2] | F(000) = 892 |
Mr = 433.93 | Dx = 1.556 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 2000 reflections |
a = 14.264 (3) Å | θ = 1.9–29.3° |
b = 6.1442 (12) Å | µ = 1.21 mm−1 |
c = 21.134 (5) Å | T = 294 K |
V = 1852.1 (7) Å3 | Prism, orange |
Z = 4 | 0.13 × 0.13 × 0.02 mm |
Data collection top
Stoe IPDSII diffractometer | 1885 reflections with I > 2σ(I) |
rotation method scans | Rint = 0.100 |
Absorption correction: numerical shape of crystal determined optically [Provide reference] | θmax = 29.3°, θmin = 1.9° |
Tmin = 0.849, Tmax = 0.980 | h = −18→19 |
10449 measured reflections | k = −8→7 |
2501 independent reflections | l = −28→27 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.079 | w = 1/[σ2(Fo2) + (0.0986P)2 + 5.0896P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.218 | (Δ/σ)max = 0.005 |
S = 1.10 | Δρmax = 0.75 e Å−3 |
2501 reflections | Δρmin = −1.52 e Å−3 |
133 parameters | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | −0.5 | 0 | 0.5 | 0.0262 (2) | |
C1 | −0.3433 (3) | 0.4633 (7) | 0.3955 (2) | 0.0328 (9) | |
H1A | −0.3903 | 0.4851 | 0.3636 | 0.039* | |
H1B | −0.2946 | 0.3714 | 0.3791 | 0.039* | |
H1C | −0.3172 | 0.6012 | 0.4075 | 0.039* | |
C2 | −0.3871 (3) | 0.3571 (6) | 0.4524 (2) | 0.0270 (8) | |
C3 | −0.3837 (3) | 0.4608 (6) | 0.5130 (2) | 0.0246 (8) | |
C4 | −0.3402 (3) | 0.6723 (6) | 0.5192 (2) | 0.0268 (8) | |
H4 | −0.3205 | 0.7437 | 0.4828 | 0.032* | |
C5 | −0.3271 (3) | 0.7707 (6) | 0.5757 (2) | 0.0269 (8) | |
H5 | −0.2994 | 0.9076 | 0.5774 | 0.032* | |
C6 | −0.3557 (3) | 0.6654 (7) | 0.6330 (2) | 0.0281 (8) | |
C7 | −0.3377 (3) | 0.7558 (7) | 0.6933 (2) | 0.0333 (9) | |
H7 | −0.3082 | 0.8904 | 0.6964 | 0.04* | |
C8 | −0.3632 (3) | 0.6474 (8) | 0.7473 (2) | 0.0374 (10) | |
H8 | −0.3498 | 0.7074 | 0.7867 | 0.045* | |
C9 | −0.4100 (3) | 0.4446 (8) | 0.7435 (2) | 0.0350 (9) | |
H9 | −0.4279 | 0.3732 | 0.7804 | 0.042* | |
C10 | −0.4290 (3) | 0.3528 (7) | 0.6858 (2) | 0.0294 (8) | |
H10 | −0.4599 | 0.2196 | 0.6836 | 0.035* | |
C11 | −0.4020 (3) | 0.4596 (6) | 0.6295 (2) | 0.0249 (8) | |
C12 | −0.4201 (3) | 0.3591 (6) | 0.56821 (19) | 0.0235 (7) | |
O1 | −0.4246 (2) | 0.1729 (5) | 0.44216 (13) | 0.0285 (6) | |
O2 | −0.4688 (2) | 0.1815 (4) | 0.56915 (14) | 0.0273 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0300 (4) | 0.0158 (3) | 0.0327 (4) | −0.0047 (3) | 0.0003 (3) | −0.0014 (2) |
C1 | 0.036 (2) | 0.031 (2) | 0.031 (2) | −0.0069 (18) | 0.0034 (17) | 0.0024 (17) |
C2 | 0.0269 (18) | 0.0209 (17) | 0.0332 (19) | −0.0028 (15) | −0.0013 (16) | 0.0024 (15) |
C3 | 0.0215 (17) | 0.0165 (16) | 0.036 (2) | 0.0016 (14) | −0.0016 (15) | 0.0008 (14) |
C4 | 0.0253 (19) | 0.0175 (16) | 0.038 (2) | 0.0003 (15) | −0.0002 (16) | 0.0039 (15) |
C5 | 0.0247 (17) | 0.0134 (15) | 0.043 (2) | −0.0038 (14) | 0.0013 (16) | −0.0027 (15) |
C6 | 0.0247 (18) | 0.0218 (18) | 0.038 (2) | 0.0020 (15) | −0.0034 (15) | −0.0091 (16) |
C7 | 0.029 (2) | 0.0261 (19) | 0.045 (2) | −0.0011 (17) | −0.0021 (18) | −0.0129 (18) |
C8 | 0.033 (2) | 0.041 (2) | 0.038 (2) | 0.003 (2) | −0.0022 (18) | −0.016 (2) |
C9 | 0.036 (2) | 0.035 (2) | 0.034 (2) | 0.0056 (19) | 0.0019 (18) | −0.0043 (18) |
C10 | 0.029 (2) | 0.0208 (17) | 0.038 (2) | 0.0002 (15) | −0.0013 (16) | −0.0017 (16) |
C11 | 0.0244 (18) | 0.0162 (16) | 0.034 (2) | 0.0017 (14) | −0.0002 (15) | −0.0039 (14) |
C12 | 0.0226 (17) | 0.0130 (15) | 0.0349 (19) | −0.0013 (13) | −0.0020 (14) | 0.0004 (14) |
O1 | 0.0356 (16) | 0.0197 (12) | 0.0302 (14) | −0.0065 (12) | 0.0012 (12) | −0.0023 (11) |
O2 | 0.0322 (14) | 0.0151 (11) | 0.0345 (14) | −0.0064 (11) | −0.0007 (12) | 0.0000 (11) |
Geometric parameters (Å, º) top
Cu1—O2 | 1.891 (3) | C5—C6 | 1.431 (6) |
Cu1—O2i | 1.891 (3) | C5—H5 | 0.93 |
Cu1—O1 | 1.944 (3) | C6—C7 | 1.415 (6) |
Cu1—O1i | 1.944 (3) | C6—C11 | 1.428 (5) |
C1—C2 | 1.503 (6) | C7—C8 | 1.371 (7) |
C1—H1A | 0.96 | C7—H7 | 0.93 |
C1—H1B | 0.96 | C8—C9 | 1.416 (7) |
C1—H1C | 0.96 | C8—H8 | 0.93 |
C2—O1 | 1.270 (5) | C9—C10 | 1.371 (6) |
C2—C3 | 1.432 (6) | C9—H9 | 0.93 |
C3—C12 | 1.422 (6) | C10—C11 | 1.411 (6) |
C3—C4 | 1.446 (5) | C10—H10 | 0.93 |
C4—C5 | 1.351 (6) | C11—C12 | 1.459 (5) |
C4—H4 | 0.93 | C12—O2 | 1.294 (4) |
| | | |
O2—Cu1—O2i | 180 | C7—C6—C11 | 118.5 (4) |
O2—Cu1—O1 | 91.92 (12) | C7—C6—C5 | 122.2 (4) |
O2i—Cu1—O1 | 88.08 (12) | C11—C6—C5 | 119.3 (4) |
O2—Cu1—O1i | 88.08 (12) | C8—C7—C6 | 120.8 (4) |
O2i—Cu1—O1i | 91.92 (12) | C8—C7—H7 | 119.6 |
O1—Cu1—O1i | 180 | C6—C7—H7 | 119.6 |
C2—C1—H1A | 109.5 | C7—C8—C9 | 120.4 (4) |
C2—C1—H1B | 109.5 | C7—C8—H8 | 119.8 |
H1A—C1—H1B | 109.5 | C9—C8—H8 | 119.8 |
C2—C1—H1C | 109.5 | C10—C9—C8 | 120.4 (4) |
H1A—C1—H1C | 109.5 | C10—C9—H9 | 119.8 |
H1B—C1—H1C | 109.5 | C8—C9—H9 | 119.8 |
O1—C2—C3 | 124.2 (4) | C9—C10—C11 | 120.3 (4) |
O1—C2—C1 | 115.2 (4) | C9—C10—H10 | 119.9 |
C3—C2—C1 | 120.6 (4) | C11—C10—H10 | 119.9 |
C12—C3—C2 | 121.8 (4) | C10—C11—C6 | 119.7 (4) |
C12—C3—C4 | 118.5 (4) | C10—C11—C12 | 120.2 (4) |
C2—C3—C4 | 119.7 (4) | C6—C11—C12 | 120.1 (4) |
C5—C4—C3 | 122.8 (4) | O2—C12—C3 | 125.4 (4) |
C5—C4—H4 | 118.6 | O2—C12—C11 | 116.0 (3) |
C3—C4—H4 | 118.6 | C3—C12—C11 | 118.6 (3) |
C4—C5—C6 | 120.4 (4) | C2—O1—Cu1 | 127.8 (3) |
C4—C5—H5 | 119.8 | C12—O2—Cu1 | 127.7 (3) |
C6—C5—H5 | 119.8 | | |
| | | |
O1—C2—C3—C12 | 2.3 (6) | C7—C6—C11—C12 | −178.8 (4) |
C1—C2—C3—C12 | −176.7 (4) | C5—C6—C11—C12 | −0.1 (6) |
O1—C2—C3—C4 | −179.2 (4) | C2—C3—C12—O2 | −8.8 (6) |
C1—C2—C3—C4 | 1.8 (6) | C4—C3—C12—O2 | 172.7 (4) |
C12—C3—C4—C5 | 4.6 (6) | C2—C3—C12—C11 | 171.1 (4) |
C2—C3—C4—C5 | −173.9 (4) | C4—C3—C12—C11 | −7.3 (5) |
C3—C4—C5—C6 | 0.7 (6) | C10—C11—C12—O2 | 6.1 (5) |
C4—C5—C6—C7 | 175.7 (4) | C6—C11—C12—O2 | −174.8 (3) |
C4—C5—C6—C11 | −2.9 (6) | C10—C11—C12—C3 | −173.8 (4) |
C11—C6—C7—C8 | 0.7 (6) | C6—C11—C12—C3 | 5.3 (5) |
C5—C6—C7—C8 | −177.9 (4) | C3—C2—O1—Cu1 | 8.6 (6) |
C6—C7—C8—C9 | −1.4 (7) | C1—C2—O1—Cu1 | −172.3 (3) |
C7—C8—C9—C10 | 1.0 (7) | O2—Cu1—O1—C2 | −10.6 (3) |
C8—C9—C10—C11 | 0.1 (7) | O2i—Cu1—O1—C2 | 169.4 (3) |
C9—C10—C11—C6 | −0.7 (6) | C3—C12—O2—Cu1 | 3.5 (6) |
C9—C10—C11—C12 | 178.4 (4) | C11—C12—O2—Cu1 | −176.4 (3) |
C7—C6—C11—C10 | 0.3 (6) | O1—Cu1—O2—C12 | 4.5 (3) |
C5—C6—C11—C10 | 179.0 (4) | O1i—Cu1—O2—C12 | −175.5 (3) |
Symmetry code: (i) −x−1, −y, −z+1. |
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