Bis(2-acetyl-1-naphtholato-κ²O,O′)copper(II)

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)°.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](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

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Computing details

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)

Crystal data

[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) Å^3	Prism, orange
Z = 4	0.13 × 0.13 × 0.02 mm

Data collection

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

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.079	w = 1/[σ^2(Fo^2) + (0.0986P)^2 + 5.0896P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Cu1—O2	1.891 (3)	C5—C6	1.431 (6)
Cu1—O2^i	1.891 (3)	C5—H5	0.93
Cu1—O1	1.944 (3)	C6—C7	1.415 (6)
Cu1—O1^i	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—O2^i	180	C7—C6—C11	118.5 (4)
O2—Cu1—O1	91.92 (12)	C7—C6—C5	122.2 (4)
O2^i—Cu1—O1	88.08 (12)	C11—C6—C5	119.3 (4)
O2—Cu1—O1^i	88.08 (12)	C8—C7—C6	120.8 (4)
O2^i—Cu1—O1^i	91.92 (12)	C8—C7—H7	119.6
O1—Cu1—O1^i	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)	O2^i—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)	O1^i—Cu1—O2—C12	−175.5 (3)

Symmetry code: (i) −x−1, −y, −z+1.